All 100+ Lonely Island Songs, Ranked from Worst to Best
For as long as humans have been able to compose music, they’ve been able to use it to make other humans laugh. Unfortunately, we all too often bifurcate quality and humor. We assume a comedic song is a novelty song, a bit of doggerel to be cast to the side of the street when its been listened to and guffawed at once or twice. The songs that radio host Dr. Demento used to play on his show are not generally held in high esteem by critics or musicologists. You can’t really feel something about a song that makes you giggle, can you?
To that claim, the Lonely Island say: bullshit.
Andy Samberg, Jorma Taccone, and Akiva Schaffer have been recording laugh-inducing ditties since they were youngsters, first under the collective name Incredibad. But it was only with their ascent to the hallowed halls of Saturday Night Live as the Lonely Island (hereafter styled as TLI) that they started affecting the course of American comedy — and, dare we say, music. The trio are an enormously talented outfit with gifts for composition in a dizzying array of genres, but their best work goes beyond mere satire and into expressions of awe at the world and its wonders. In honor of the group’s first live tour, we have assembled a definitive ranking of their massive catalog, from their earliest lo-fi goof-offs to their expertly assembled recent work.
Although many of these songs have accompanying visuals in the form of music videos, SNL Digital Shorts, and even filmed appearances in their underrated 2016 film Popstar: Never Stop Never Stopping and the recent visual album The Unauthorized Bash Brothers Experience, we have chosen to evaluate each one on its merits as a standalone musical entity. We have also excluded their occasional skits (although, if we were to rank those, “Normal Guy” would, of course, be number one).
112. “Owen’s Song,” Popstar: Never Stop Never Stopping (2016)
I’ll say this: I admire TLI for even bothering to release this plot-advancing 98-second snippet of EDM stupidity from the Popstar film as a track. The deft production makes for a beat of convincing mimicry, but despite the title, this doesn’t really add up to a song.
Best/Only Lyric: “Earth, wind, and birds / They fill my heart up with darkness, so cold.”
111. “Maximus,” Popstar: Never Stop Never Stopping (2016)
Podcaster Tom Scharpling used to have this thing called the Frankie Teardrop Challenge. In order to win it, you had to listen to the entirety of Suicide’s infamously horrifying “Frankie Teardrop” alone while wearing headphones and not lose your mind. One could set up a similar test of will with “Maximus,” Popstar’s ode to a perished turtle. It’s essentially two and a half minutes of listening to Andy’s blaring, autotuned voice with no backing track other than a lone synth near the end. Once he starts weeping, I always think to myself, I’m not Joanna Newsom, I am under no obligation to listen to Andy Samberg cry.
Best Lyric: “I miss you, my old friend / You took a little doo-doo in my hand.”
110. “Spell It Out,” The Wack Album (2013)
The flutes and whistles of the beat can’t make up for the fact that this isn’t a song so much as it is a word puzzle with an idiotically vulgar secret message. Who cares?
Best Lyric: “Lenny!”
109. “We’ll Kill U,” online video (2011)
The ongoing Guy Number One / Guy Number Two song cycle reaches its nadir with this sucker. The bits are fun when they follow the Guys as they navigate their quotidian existences, but in this track, the humor is derived from the fact that we’re listening to two stereotypically “white” characters adopting the more violent aspects of racist stereotypes of people of color. Even if you don’t find that offensive, it’s hard to argue that it’s anything more than a cheap gag. Snore.
Best Lyric: “Each jerk we kill, our hearts grow colder / I could shoot all day, doesn’t hurt my shoulder.”
108. “Iran So Far,” SNL Digital Short (2007)
At the risk of sounding too woke, I have to say, as a queer man, this is the rare TLI track about queer male sexuality that I find actively offensive. Gay panic isn’t funny, even if you’re using it to lambaste a homophobe like Mahmoud Ahmadinejad! And, again, the problem isn’t just that it’s a touchy subject, it’s also just hack. I guess 2007 was a long time ago.
Best Lyric: “And even though I disagree with almost everything you say / You ain’t wrong to me / So strong to me / You belong to me / Like a very hairy Jake Gyllenhaal to me.”
107. “Awesometown Theme Song,” Please Incredibad Don’t Hurt ’Em (2005)
This is barely a song, but it’s an early demonstration that Andy, Jorm, and Kiv were able to play around in wholly non-rap genres and come up with something serviceable and at least mildly clever. If they hadn’t broken into SNL, they could’ve been great jingle writers.
Best Lyric: “My name is Jorma, motherfucker / The sensitive one / Break your motherfucking face with the butt of my gun!”
106. “Ashley Wednesday,” Popstar: Never Stop Never Stopping (2016)
Popstar’s saccharine and syrupy “Mona Lisa” reprise is 100 percent skippable. Nothing funny happens and the melody is regurgitated from a far better track. The only reason this isn’t in, like, the bottom three is that I just can’t deny Seal’s dulcet pipes. We’re overdue for a Sealaissance, to be honest.
Best Lyric: “Step into my carriage / We’ll park inside my garage.”
105. “Metaphor,” Please Incredibad Don’t Hurt ’Em (2005)
The best thing I can say about “Metaphor” is that it’s the kind of grainily recorded comedy detritus that you’d download from Napster at age 13, find enormously funny, and learn how to play guitar just so you can do it for your friends. You later look back on this decision and are glad you learned how to play the guitar, but you have to do some serious work in therapy to forgive your younger self for crimes of good taste. It’s only notable in that it sounds nothing like anything they’d done before or have done since, which is absolutely for the best.
Best Lyric: “Flank steak is delicious / Wish I was eatin’ it right now / And every time that I see one / I wanna titty-fuck the flank steak / ’Cause it’s a metaphor / For fuckin’ flank steak.”
104. “My Pants,” online video (2005)
Inoffensive and cute but utterly forgettable. I guess it’s worth noting that, at 29 seconds, this is the shortest TLI song ever released. Only necessary for true Jorm completists.
Best Lyric: “Why does everyone make fun of my pants? / They’re just pants, why not give ’em a chance?”
103. “I’m a Hustler,” The Wack Album (2013)
Another instance of TLI’s cultural-appropriation bugaboo rearing its weasley head: a “white”-sounding character does a stilted job of rapping lines about doing something that racist caricatures of black people do — in this case, dealing crack cocaine. One wants to shake the lads by the shoulders and scream, “You’re better than this!”
Best Lyric: “You have to be born with a certain swag / A je ne sais quoi that makes hustling your bag.”
102. “Trouble on Dookie Island,” Turtleneck & Chain (2011)
Christ, do I hate this song. Maybe I’m just a fecalphobe, but I simply can’t get myself to find jokes about feces to be anything other than stomach-churningly gross. Given that that’s literally all this song is about, this is probably my least-favorite TLI song. However, this is a list of the best, not my personal ranking, and “Trouble on Dookie Island” at least features competent production and I’m sure someone enjoys this sort of thing, so I’m giving it the benefit of the doubt.
Best Lyric: “We hit the dirt, this rottweiler snarlin’ and smilin’ / He ripped my pant-leg off, a bunch of dookies went flyin’.”
101. “Cool Beans,” Hot Rod (2007)
Oh right, “Cool Beans.” There’s no particular reason for this remix of two men saying the words “cool beans” to each other to exist. Nothing of note happens and the whole thing feels like a final project for a ProTools 101 course. Yes, B-Legit shows up to do some generic rhymes about being a gangster, but it feels like running a marathon to get from the beginning of the track to that part, and it’s hardly a reward. Pass.
Best Lyric: “Cool beans!”
100. “Semicolon,” The Wack Album (2013)
I mean, I get it. The joke is about how hip-hop is plagued by that kind of lazy wordplay where you say a thing and then abruptly say a slightly related thing as a kind of auditory hashtag. So here, we get TLI running through a million examples of that notion, fumbling around in the dark as they search for an execution of the concept that actually makes you do anything other than silently acknowledge an attempt at a gag. But Solange sounds great, so this one gets a bump up from the bottom of the heap.
Best Lyric: “I’m loud and I’m zipping around: jet ski / Your dick is little like Wayne: Gretzky / But Gretsky’s got a big dick: clarification / Everyone was rude to me: Paris vacation.”
99. “Thumpasaurus,” demo (2002)
I can’t really tell you what the conceit behind “Thumpasaurus” is. I guess it’s a series of vignettes about bystanders who witness a monster attacking a city? I guess it’s fine?
Best Lyric: “Thumpasaurus / This is the chorus / Not Tour de France / But it’s our tour de for-us.”
98. “We Are a Crowd,” The Wack Album (2013)
I’m not exactly sure why TLI chose to write, let alone record and release this song. It’s not bad, it’s just totally pointless. Are there really that many songs about crowds singing together at sporting events? Plus, there’s no narrative to the endeavor, which means you’re left with a woeful flatness of delivery and theme.
Best Lyric: “We’re gonna cheer, ’cause we are here / With all of us together, we have nothing to fear.”
97. “I Think I Might Have Killed the President,” Please Incredibad Don’t Hurt ’Em (2005)
This one feels a lot like a short story a fifth grader might compose, find hilarious, and get in trouble for writing. It’s a reasonably coherent (which can’t always be said for early TLI) musical tale and the arch vocal delivery from Kiv is sorta entertaining. It does, however, feature the group’s weird obsession with abusing the homeless, so that’s a point not in its favor.
Best Lyric: “Well it’s been a year now, since that fateful event / I framed a hobo to take the cops off my scent / And every time I hear a bell, I stab someone in the face / But besides that, I’d say that everything is going great!”
96. “Hugs,” The Wack Album (2013)
There are a lot of TLI songs where the conceit works because of the contrast between the harshness of the music and the wholesomeness of the words. “Hugs” attempts that magic trick and largely fails. Perhaps the contrast is too extreme and thus shades into abstraction? I find Pharrell’s vocals mildly enchanting, but that could definitely be because the rest of the track is so dull.
Best Lyric: “Hugged so many ladies, arms shaky and shit / Because I’m the Wilt Chamberlain of the upper-body grip.”
95. “Cool Guys Don’t Look at Explosions,” MTV Movie Awards video (2009)
One of the least Lonely Island-ish of all the Lonely Island songs. It feels like a pretty standard-issue SNL goof-off song-skit from the days before TLI revolutionized the genre, right down to the presence of a faux-basso Will Ferrell. Like a few others on this list, it only really works if you can see the video at the same time, which makes it suffer as an independent musical work.
Best Lyric: “Keyboard solo, J.J. Abrams!”
94. “Rocky,” Turtleneck & Chain (2011)
You have to give TLI credit for going deep on the object of their parodizing here. It had been decades since the Fresh Prince and DJ Jazzy Jeff released “I Think I Can Beat Mike Tyson” when “Rocky” was released, so the idea of a rapper challenging a boxer to a duel wasn’t exactly a zeitgeist-y topic. The song relies almost entirely on its granular descriptions of ultraviolence and, by that standard, it more or less pulls off what it needs to do.
Best Lyric: “I was quivering and twitching when I soiled my shorts / Then Rocky pissed on me — customary in sports.”
93. “Ka-Blamo!” Please Incredibad Don’t Hurt ’Em (2005)
A mediocre ode to categorization. In this track, the boys posit that everything in life can be defined as either “ka-blamo” (good) or “not ka-blamo” (bad). That’s more or less the entirety of the song’s pitch, and it pulls it off decently.
Best Lyric: “When you’re mining for coal and you forget what coal is / And you’re sure to be fired, because that’s your job!”
92. “Go Kindergarten,” The Wack Album (2013)
TLI have a penchant for lampooning the ways in which people choose to have fun, and that’s never been more clearly on display than in this tolerable track. As the modes of enjoyment get more extreme, you keep expecting to find yourself guffawing, but the best the song can draw out is a few appreciative chuckles.
Best Lyric: “Have a motherfucking baby on the floor / Raise it in the club, home-school it by the door.”
91. “Hey Ya Ho,” Popstar: Never Stop Never Stopping (2016)
Chris Redd’s rapping is stunning on his Popstar tracks, and that’s definitely still the case when it comes to “Hey Ya Ho.” But — and, again, I hate to make everything political — the title and its accompanying premise of the narrator being as savage as a stereotypical Native American is deeply offensive in a way that can’t be excused by its intention to ape the button-pushing of Tyler, the Creator.
Best Lyric: “Fuck your whole team and that horse you rode in on / Seriously, the horse looks great / (Hunter!)”
90. “Donkey Roll,” Popstar: Never Stop Never Stopping (2016)
A riff on songs that urge the listener to engage in a particular dance sequence, “Donkey Roll” serves a somewhat crucial plot purpose in the film of Popstar, but as a song, it’s just a bit of mild fun. The beat is a convincing attempt at late-’80s synth nonsense, the moves described are silly, and the aggressively pitch-shifted uttering of the title words is pretty fun. Not much else to write home about.
Best Lyric: “Don’t be a MILF and just let me see that Donkey Roll.”
89. “Daddy,” The Unauthorized Bash Brothers Experience (2019)
The weakest point in an exceedingly strong work of art. The Unauthorized Bash Brothers Experience EP is one of the finest products TLI have ever produced, but “Daddy” feels a little too on-the-nose to merit its status as the closing track. The beat is appropriately desolate and there’s a certain amount of pathos in a line like Kiv’s agonized “Daddy, do you hear me cryin’? Daddy, can you see I’m dyin’?”, but not enough to elevate this one into the heights of the group’s catalog.
Best Lyric: “Buy all my steroids in bulk (Costco) / Wanna be big as the Hulk (Hogan) / Stronger than Wolverine teeth (Logan) / Answer to ‘Where’s the beef?’ (Slogan)”
88. “Shrooms,” Incredibad (2009)
Look, “Shrooms” is lowkey a banger. Sure, it’s only 34 seconds long and solely consists of the guys yelling, “I’m on shrooms!” “Yeah!” and “La la la” on top of a synthesizer. But the thumping hyper-pointillism of the 8-bit beat would have been a great backing track in F-Zero for the Super Nintendo, and I mean that as praise.
Best/Only Lyric: “I’m on shrooms! (Yeah!)”
87. “Zanzabar,” Please Incredibad Don’t Hurt ’Em (2005)
Okay, so, on a personal level, “Zanzabar” is one of my favorite early TLI tracks. But objectively, it’s got a lot of problems. For one thing, the narrative is pretty incomprehensible: I guess it’s about a white adventurer in some non-Western desert who has a Peter Lorre-voiced wolf sidekick, and it’s revealed that the sidekick is making the whole story up in his room? Plus, there are weird toss-off references to the title character raping said sidekick, which is a trope TLI thankfully never chose to explore again. These are serious demerits, but Andy’s Will Ferrell-esque delivery is genuinely charming and the beat is as sick as it gets.
Best Lyric: “Zanzabar, raised by the wolves / Oxford education as phrased by the wolves.”
86. “The Old Saloon,” Incredibad (2009)
To be fair, “The Old Saloon” is supposed to be bizarre and hard-to-follow. At least I think that’s the case. The vocals are jammed together like Venn Diagrams and the fictitious DJ keeps yelling his own name at key lyrical points. The whole thing becomes a little amusing by song’s end, but you can’t really remember what you just listened to, except for that narcissistic DJ’s moniker.
Best Lyric: “DJ Larry!”
85. “When Will the Bass Drop?” SNL Digital Short (2014)
Another song that really only works if it’s paired with its video. Taken on its own, there’s nothing even resembling a conceit — it’s just an exercise in assaultive dubstep. But hey, it does that surprisingly well! Whoever produced this one really knew how to get the party moving, even if there’s nothing to laugh at.
Best Lyric: “Get turned up to death!”
84. “Shy Ronnie,” SNL Digital Short (2009)
I expect to get in trouble for putting “Shy Ronnie” and its sequel so far down on this list. I accept that. I don’t know, man, I just don’t see why we should think these things are so funny. The concept is so threadbare and the main fun parts are when Andy finally bursts into aggressive gangsta rap, which are, of necessity, parts that only last a few seconds. The videos improve them a little bit, but not by nearly enough. They’re wastes of perfectly good Rihanna availabilities.
Best Lyric: “Oh boy / Should have just paid Kanye.”
83. “Shy Ronnie 2: Ronnie & Clyde,” Turtleneck & Chain (2011)
See above. The only reason this is higher up than the original is the increased absurdity of Andy’s portion.
Best Lyric: “Don’t get the name twisted, ’cause I’m crazy as shit / I hung a giant-ass noose off my giant-ass dick.”
82. “Saturday Night,” Please Incredibad Don’t Hurt ’Em (2005)
This is the earliest instance I can find of one of my favorite of the group’s tropes, which I call “narrative drift.” The song starts out on one clear topic (in this case, the dull notion of otherwise-straight dudes hanging out to engage in sex acts while watching porn on a Saturday night), then gradually shades into something wholly unrelated (an ode to pro tennis player Michael Chang). In “Saturday Night,” the drift is wholly welcome because the initial idea is pretty thin and the endpoint is genuinely hilarious.
Best Lyric: “When we rhyme about tennis, you know we’ll always be drunk / My man Michael Chang’s got legs like a tree trunk.”
81. “Everybody Dance,” Please Incredibad Don’t Hurt ’Em (2005)
There’s no clear conceit for “Everybody Dance,” but it really doesn’t matter. I suppose you can interpret it as a bunch of vignettes from various people enjoying themselves at a nightclub? Whatever, the beat and vocal performances go so hard that you can’t help but shake your booty and giggle a little.
Best Lyric: “Your jam’s on / The jimmy jam song / This is your time to get your jimmy jam on / Hey jimmy / No, it’s jimmy jam / Time to slam bam / It’s your jimmy jam.”
80. “Everything Is AWESOME!!!” The Lego Movie (2014)
Pure sugar. In this kid-friendly, sorta-diegetic song from The Lego Movie, TLI supplement Tegan and Sara with uptempo rapping about how lovely life can be and if you can’t crack a smile at the end result, I’m not sure what your deal is.
Best Lyric: “A Nobel prize, a piece of string / You know what’s awesome? Everything!”
79. “Ras Trent,” Incredibad (2009)
This gentle poke at white trustafarians just barely avoids being racist and is, in fact, quite catchy. The narrator’s embrace of the tropes of reggae without any awareness of their racial and socioeconomic underpinnings is a solid gag — and, in a way, a bit of self-awareness about their own career-long skirting of the line between appreciation and appropriation.
Best Lyric: “Have you ever noticed how baldheads suck? / Bada-ding-ding-ding-ding-dong-ding-ding-dong duck / Excuse I for my skanking, give thanks and praise / Me toil part time at jah Cold Stone Creamery.”
78. “Legalize It,” Popstar: Never Stop Never Stopping (2016)
There isn’t a ton going on in “Legalize It” — it’s just a story about how a guy got addicted to crack after accidentally smoking some during an intended marijuana session. But the trippy dub beat, endlessly catchy chorus, and Andy’s intense vocal performance make it a worthwhile listen. That said, guys, can you lay off the jokes about crack?
Best Lyric: “I love crack (holy shit) / And now I am invincible (fuck yeah) / If anyone tries to take my crack / I’ll kill them on principle.”
77. “Wait (You Guys),” Please Incredibad Don’t Hurt ’Em (2005)
Hey, remember the Ying Yang Twins? I sorta do! This track serves solely as a vehicle to parody that duo’s profoundly rapey “Wait (the Whisper Song)” and pulls off its mission with flying colors. Like some of the best TLI songs, it takes the macho overconfidence of the original and excavates the beta-male desperation that was always just beneath the surface.
Best Lyric: “Hey, pretty girl, did you go to college? / Did you get your B.A. with all that knowledge? / I like your boobies in your shirt / Please let me show you my penis.”
76. “Meet the Crew,” The Wack Album (2013)
TLI wouldn’t have gotten as far as they have if they weren’t good at vocal chameleonship, and this track is where they show that skill off to its fullest extent, embodying dozens of one-off characters in a Wu-Tang-esque roundup. I’m particularly glad that Jorm finally gives a name — “Smooth Guy” — to the character he’s used in “Punch You in the Jeans” and “I Don’t Give a Honk.” World-building, folks!
Best Lyric: “I’m a little lost / Is this the right studio? / I work for Rod Stewart / You know what? I’m gonna go.”
75. “Cocaine,” single (2004)
“Cocaine” stands alone in the TLI corpus in that there is nary a trace of a wink in it. It’s a completely straight-faced rap about a trio of men who both snort and sell cocaine, performed with extreme brashness and braggadocio. On the surface, there isn’t a single joke; however, the joke is, of course, derived from the listener’s knowledge of who they’re listening to and that this is all a pastiche. It’s not a work of genius, but that commitment to the bit is compelling and the lyrics are bizarrely evocative. Plus, it introduced the below lyric, which was then copied, word-for-word, in the far superior “Focused AF.”
Best Lyric: “Walk in the party with my dick in my hand / Then straight to the bathroom with my dick in my hand / You wanna step up, I got the brick in my hand / Then leave your ass face-down with my dick in my hand.”
74. “Things in My Jeep,” Popstar: Never Stop Never Stopping (2016)
One marvels at the sheer audacity of even bothering to record this song, much less do so with the late Chester Bennington of Linkin Park. It stems from a stupid joke in the film of Popstar and we should all be glad that the boys chose to bring it to life. It remains too dumb to be very high on this list, but it’s a hell of a lot better than it should be.
Best Lyric: “Hi, come inside, look around my Jeep / You will find such marvelous things / A broken stapler, some crumpled paper / Prepare for adventure, inside my Jeep.”
73. “Feed the Beast,” The Unauthorized Bash Brothers Experience (2019)
“Feed the Beast” is the most predictable song on Bash Brothers. Lyrically, it’s just a list of the things that rich and desirable men get stressed about, from crowds to crabs. The music rises to that particular occasion with a fair amount of technical skill, its electronic warbles and wet drums reminding us that the fictional Jose Canseco and Mark McGwire have no one they can truly trust. The thing that keeps this one from being totally skippable is the oddly moving sequence at the end when Andy / Jose lists all the people he feels close to without seeming to realize that they’re all either paid by him or destined to betray him. It’s a fine track, but I get why they chose not to include it in the film version.
Best Lyric: “My mom / My burden / I’m not / A virgin!”
72. “Japan,” Turtleneck & Chain (2011)
The originality of the concept is what keeps this one as high up in the list as it is: the TLI guys decide they want to go to Japan so they record a single with so many specific references to locations and activities there that the label will be required to fly them to the Land of the Rising Sun for the music video. The narrative drift toward a bizarre obsession with throwing things in a river is fun, too, and the fact that it never really gets racist is a nice surprise.
Best Lyric: “We’re three cool white friends in Japan / The fact that we’re white isn’t why we’re friends / But we are white and we’re friends.”
71. “Daiquiri Girl,” SNL Digital Short (2008)
I can’t exactly explain the charm of “Daiquiri Girl.” It shouldn’t work as an independent song, given that the primary joke of this Digital Short bit is visual in nature. And yet, it feels so sweet and kind and lovely that you can’t help but fall in love with it a little bit. Sip away, Andy.
Best Lyric: “When I first met you, you were not a daiquiri / Then you went and had a scientific discovery / One part rum, two parts ice / Three parts love, you are so nice.”
70. “Sax Man,” Incredibad (2009)
It’s only fitting that Jack Black would appear on the first real TLI album, as the group is in many ways the inheritor of the goof-off mantle of Tenacious D. Black, as always, completely commits to the silly and slightly hard-to-comprehend bit and the joke — a guy keeps introducing a musician who sucks — feels like it could have emerged from vaudeville. The song also features a great TLI trope, later repeated in “Jack Sparrow,” which is the idea that the performers can’t stop performing the song even though it’s going horribly awry. Y’know, like life.
Best Lyric: “Well, he was a sax man from the state of Tennessee / First sat in with the band at the ripe old age of three weeks old.”
69. “Ardy Party,” Please Incredibad Don’t Hurt ’Em (2005)
As noted earlier, TLI have a bad habit of using street cocaine and the homeless as narrative props, and that tendency has never been more apparent than it is on this early TLI song. However, the construction and performance of the song are so fantastic (and the unwoke era from which it emerged so different) that one partially forgives the shortcomings of the premise. I simply adore this hardcore, over-the-top ode to a party guy whom two men both admire and abuse, and it employs the TLI motif of repeating one non sequitur detail (in this case, the title character’s love of wearing sandals with socks) to a point where it becomes outright hilarious.
Best Lyric: “If Ardy ever stopped rocking you know we would kill him / Roll him up in a carpet and throw him off of a buildin’.”
68. “Oakland Nights,” The Unauthorized Bash Brothers Experience (2019)
TLI are sorta the victims of their own success on this one. They’ve already composed so many excellent songs about doofy douchebags attempting to seduce women that “Oakland Nights” can’t help but pale in contrast to, say, the legendary trio of Andy / Justin Timberlake R&B collaborations. Nevertheless, this one gets the job done without making any unforced errors and the steam-room echo of the production is evocative. One wishes Sia had more interesting things to do here, but her presence is always welcome.
Best Lyric: “Ooh, that shit is sexy / Tell the maitre’d at your booty to expect me.”
67. “Turtleneck & Chain,” Turtleneck & Chain (2011)
Much like the superior “Santana DVX,” this little ditty riffs on the idea, first popularized in Run-DMC’s “My Adidas,” that listeners for some goddamn reason would want to hear about the favored consumer products of their musical idols. The joke is a little weak, what with its reliance on the contrast between the hardness of rap and the softness of the attire, but the elaborate descriptions of the titular jewelry and shirts make it a fun one.
Best Lyric: “Got more chains than the snow patrol / Every one razor-thin like an insect stripper pole.”
66. “Ibitha,” Popstar: Never Stop Never Stopping (2016)
As is so often true of TLI songs, the conceit here is almost astoundingly stupid: what if you performed a song about Spain using a Spaniard’s lisp? However, the beat is so lofty and thrilling and the bit where Andy just starts listing the ingredients of paella makes this one to remember.
Best Lyric: “Our tummies are full of paella / Here’s a recipe of the paella.”
65. “Just 2 Guyz,” Please Incredibad Don’t Hurt ’Em (2005)
The introduction of Guy Number One and Guy Number Two manages to avoid the racial insensitivity of the characters’ “We’ll Kill U” and, although it doesn’t ascend to the heights of their “We Like Sportz” or “We Need Love,” it’s still very entertaining in the way it celebrates (as TLI so often do) male friendship. The narrative drift into aggression toward the listener is fun and sparing and the overall result is a charmer.
Best Lyric: “How would you like to be shot? / Me and my friend smoke pot.”
64. “Should I Move?” Popstar: Never Stop Never Stopping (2016)
An epic drama of the one percent. This track is perhaps the best summation of Andy’s Conner4Real character from Popstar, what with his completely tone-deaf angst about whether he should buy a second home just after buying a different one, and the depth of his torment pairs well with the story’s even-more-tone-deaf conclusion. Plus, we get some prime time with Akon, TLI’s most prolific superstar collaborator.
Best Lyric: “I had to get away so I flew to Majorca / Dove in the ocean, went swimming with orca / I drank too many piña coladas and fell asleep / Had a dream about both houses and began to weep.”
63. “Me Likey Dat,” Popstar: Never Stop Never Stopping (2016)
BWAMP-bwomp-BWAMP-bwomp — so begins this infectiously catchy little piece of fluff. It’s partially an improved version of the concept from “Ka-Blamo!” with the added delight of describing how the TLI’s Popstar doppelgangers, the Style Boyz, like to attend parties: i.e. completely naked and smoking weed. There’s something so endearingly stupid about the repeated titular cry that you can’t help but grin.
Best Lyric: “When the girls blow us kisses: me likey dat! / And when your momma does our dishes: me likey dat! / When a genie grants wishes / About girls blowing kisses / And your momma doin’ dishes: me likey dat!”
62. “Who Said We’re Wack?” Incredibad (2009)
I distinctly remember hearing Incredibad for the first time and being blown away by the comedic aggression of this opening track. Though my admiration for it has dimmed with time, it remains a solid effort, diving into the assertive paranoia of a rap group so insecure that they can’t stand the very idea of being dissed. It’s the princess and the pea of hip-hop.
Best Lyric: “How could a person up and call a person wack? / How could the devil turn the blue sky black? / How many babies born will never reach their dreams? / And how could a person call another person wack?”
61. “We Like Sportz,” Incredibad (2009)
This Guy Number One / Guy Number Two expedition is brutally simple in its premise: two guys, uh, like sports and want to tell you about it. I’m not exactly sure what kind of song it’s supposed to be parodying, but the narrative drift into silly personal declarations that have nothing to do with sporting events puts it over the top into being entertaining.
Best Lyric: “I drink whiskey cause I like the taste / You think it’s bitter but I think it’s great.”
60. “Incredibad,” Incredibad (2009)
As the superhero movies tell us, every team has an origin story. In this chronicle of a foursome sexual encounter with an extraterrestrial, TLI present us with a driving backing track and a tale that, as per usual, manages to be cute and celebratory without being homophobic. Not their best story-song, but a solid one.
Best Lyric: “Three-way climax, best friends forever / What a blessing to have lost our virginity together.”
59. “Focus on the Game,” The Unauthorized Bash Brothers Experience (2019)
What’s weird about “Focus on the Game” is that there aren’t any jokes in it. Not a single one. That is, in a way, admirable — as is true of so much on Bash Brothers, the song demonstrates a maturity and willingness to take emotional risks that wasn’t present in Popstar. Here, Andy and Kiv deliver what are essentially a pair of soliloquies that would fit perfectly well in a piece of musical theater, where two characters are making the pain in their hearts known to the audience in song form. The highlight is the haunting foreshadowing of the final line, the irony of which the group wisely and surprisingly never really delves into within the plot of the album. We don’t need the men’s eventual falling-out to be made explicit in Bash Brothers because the work is not a narrative so much as a vignette of a brief moment when everything was going right and no one was happy about it.
Best Lyric: “And if one day they should come for us and strip us of our crowns / I know that, if I am going down, you’re also going down.”
58. “Great Day,” SNL Digital Short (2010)
It’s sort of bizarre that this one never made it to an album, as I seem to recall it being pretty popular when it made its SNL debut. It’s about as far removed from rap as you can get, with its whistling woodwinds and zip-a-dee-doo-dah attitude toward a manic drug binge. I’d argue it’s even better without the video component, which always struck me as the worst kind of Samberg broadness.
Best Lyric: “Something today makes me feel fine and fancy-free / Much of the ocean is still unexplored, how did I get up in this tree?”
57. “You’ve Got the Look,” The Wack Album (2013)
Back in college, I knew this one girl who went to a party and accidentally released a breast from her dress. A friend told her about the faux pas and she paused, looked the friend dead in the eye, and said, “Titties gotta mingle.” The object of “You’ve Got the Look” is her spiritual cousin, wandering a party with a single boob swinging free. I love the fact that the song spends whole minutes on an internal thought process — is that intentional? — that could only have lasted seconds before the lady fixed the situation. Kristen Wiig’s abrupt turnabout coda takes it from good to very good.
Best Lyric: “Squirrel, you’re the center of attention / Tell me, is that good or bad? / ’Cause if it’s not on purpose, it would be really sad.”
56. “2 Banditos,” Popstar: Never Stop Never Stopping (2016)
Chris Redd is an indisputably better rapper than Andy Samberg, and the latter elevates his game when he has to verbally spar with the former on this track. They spit rhymes at a charging pace and their evocatively conjured boasts are a delight to the ear. The lyrics are relatively dull and aimless, but the delivery is aces.
Best Lyric: “Yeah, I’m also on my white-boy shit / That’s my birthright.”
55. “100th Digital Short,” SNL Digital Short (2012)
A delicious smorgasbord. If you’re a TLI superfan, this non-album track will make your heart sing as it runs through the rolodex of characters that the group has conjured up over the course of their rise to power. Oh, and Justin Bieber’s there, too. I used to date someone who, prior to this song’s release, always used to say the culmination of TLI’s sex obsession would be an act of autofellatio, and this song proves her absolutely right.
Best Lyric: “I was tricked into doing this / I don’t endorse this song / No, no, no, no, no.”
54. “Attracted to Us,” Turtleneck & Chain (2011)
As my colleague, Jesse David Fox, once pointed out, you can argue that TLI’s whole deal is that they’re parodying toxic masculinity and the very idea of what it means to be a man. That idea powers “Attracted to Us,” in which the boys assert their appealing natures over and over, only to undercut it all by pointing out that the opposite sex will never get to taste their forbidden fruit because they’re too shy. Somehow, they’re not sad sacks about it, but instead seem triumphant in this act of self-awareness. Beck pops in for some hypnotic vocals and, given his historic commitment to goofball white-boy rap, this feels like a father-and-sons reunion.
Best Lyric: “Space girls! / You are attracted to us! / In-your-face girls! / You are attracted to us!”
53. “Mama,” Turtleneck & Chain (2011)
In this update of the final section of “Zanzabar,” TLI find themselves in an increasingly heated argument with their mother (I guess they’re brothers now?) over her attempts at affection while they’re recording, ironically enough, an ode to their love for her. The joke should get old, but TLI wisely prevent that from happening by upping the ante of their fury with every passing interruption and keeping that in stark contrast to the persistent calm of the mother. By the time Dad shows up, you’re in stitches. Not much of lasting thematic value, but a fun one, to be sure.
Best Lyric: “Just checking on my guys!”
52. “I Run NY,” The Wack Album (2013)
The first time I heard “I Run NY,” in the final months of Michael Bloomberg’s three-term tenure as mayor of New York City, I was disappointed that the lyrics don’t seem to exactly correspond to the travails of that controversial billionaire technocrat. But as time has gone on, I’ve realized I’m an idiot. This is a really, really fun song about the frustrations of leadership and one man’s eternal battle against fire-breathing mutant rats, and I’m now more than satisfied that Andy at least nailed the Bloomie impression in the intro.
Best Lyric: “Yo, I double literally run New York: I run the marathon / Plus I organize it, so I double run the marathon / But no one seems to give a fuck that I’m a paragon / Instead, they Photoshop me so it’s looking like I wear a thong.”
51. “IHOP,” The Unauthorized Bash Brothers Experience (2019)
The beat here is frickin’ sick. The unnerving human yips and yodels that populate the sparse backing track are hardly what the International House of Pancakes would want to be musically associated with, but they capture the loneliness of a late-night visit to the dining establishment with aplomb. There are two bits in the lyrics that stand out, one for each protagonist: Jose shouting, “Hit the ball so fucking hard you can hear the cow it came from scream” and Mark’s jaw-droppingly funny and tragically brief visit to to the puka-shell shop. Not anywhere near the best song on Bash Brothers, but an admirable effort.
Best Lyric: “Yo, shut the fuck up and put the pukas in the box.”
50. “Perfect Saturday,” The Wack Album (2013)
God, what a story. One thinks it’s gonna be a riff on Ice Cube’s “It Was a Good Day” or Ludacris’s “Saturday (Oooh! Ooooh!)” and, for a little bit, it is. Then things get gross. Then they get shockingly dark. By the time we hear Andy yelling directly at the listener on this album-ending endeavor, we’ve forgotten how weak most of The Wack Album is.
Best Lyric: “This is Lonely Island! Oh, ’cause we got a little paper now and you see us on the TV, you think we don’t do fart jokes no more?”
49. “Equal Rights,” Popstar: Never Stop Never Stopping (2016)
The joke isn’t the point. The performance is. Ostensibly a parody of Macklemore’s treacly and cloyingly performative ode to the gays on “Same Love,” “Equal Rights” gradually shifts into what is easily Andy Samberg’s most dazzling display of rapping skill. The final verse will leave you breathless.
Best Lyric: “True love trumps all / Predator / Flying kicks, not gay, big watch / Not gay, missionary / One Love / Gym socks, nunchucks, and not gay / Lighter fluid, HD, ninja / World peace / Four-wheel drive / Gay marriage / Love beav / Free love / Golf clubs / Two guys / Not gay / Rainbow / Muff dive / Harvey Milk, Sean Penn / Not gay / Drum solo, courtside seats / Same sex / One-armed push ups / Lynyrd Skynyrd.”
48. “I Fucked My Aunt,” The Wack Album (2013)
Once again, we’re presented with a TLI track where the conceit doesn’t totally make sense, but that only adds to the charm. The title and first two verses would suggest that the song is about incestuous relations with a parent’s sister, but over and over, they seem to say that’s not exactly what happened. You get to the part about fucking an ant and you’re all in, and then Akon pops up and takes the whole thing home to glory. And the beat is weirdly sexy? Look, I’m as confused as you are.
Best Lyric: “I mean, I fucked my aunt, too, but you don’t see me making songs about it / Although we technically didn’t have sex / Just some above the clothes stuff / And some under the clothes stuff / I mean, what is sex, really? Is it just penetration? / Or do you have to finish? ’Cause I finished.”
47. “The Compliments,” The Wack Album (2013)
Another TLI song about mutual male boosterism that is surprisingly inspiring and sweet. It’s lovely to hear the boys bark out praise for one another and although Too $hort’s appearance is juuuuust this side of gay panic, the song as a whole is somehow as funny as it is kind.
Best Lyric: “Yo, you talking feminism? Andy loves that shit / Plus the femme fatales love him ’cause he’s got good dick.”
46. “Karate Guy,” Popstar: Never Stop Never Stopping (2016)
It’s hard to say, exactly, what “Karate Guy” is supposed to be lampooning. Figures of speech, I guess? And yet, against all odds, this is one of the better songs in the midlist of their catalog. It’s just so chill, the way they earnestly croon about the literal nature of having a nice time, and the chorus feels anthemic for reasons I can’t quite explain.
Best Lyric: “It could be any temperature / 60° or 80° / There just has to be friends / And drinks and ladies.”
45. “Sick Glenda,” Popstar: Never Stop Never Stopping (2016)
We’ve already noted how much TLI owe to Beck and Tenacious D, but there is no musical act to which they are more indebted than the Beastie Boys. Both triads knew there was a way to mine laughs from hip-hop without the blunt idiocy of, like, “Rappin’ Duke” or whatever. “Sick Glenda” is wholly indistinguishable from a Licensed to Ill-era Beasties track and that imitation-as-flattery makes one’s heart warm right up.
Best Lyric: “Sick Glenda, Sick Glenda / Get better or fuck you.”
44. “Turn Up the Beef,” Popstar: Never Stop Never Stopping (2016)
Like so much in the soundtrack to Popstar, this track could have just been a non-musical line of dialogue or a fragment of a song, but the guys chose to go all-out and record the entire goddamn thing. Here, the idea is that Conner4Real burst onto the scene as a solo act with a verse where all he did was shout catchphrase tags, and one sits in awe at the sheer number of them that TLI were able to come up with. And hey, God bless Emma Stone for showing up to do the accompanying vox — she’s actually quite good at it!
Best Lyric: “Patrick! Stewart! Money!”
43. “Jose & Mark,” The Unauthorized Bash Brothers Experience (2019)
The first time you hear the chorus to “Jose & Mark,” you think you’re going to get sick of it. I mean, it just consists of Andy screaming, “They call me Joseeeeeeeee” for eight solid seconds and Kiv following that with a murmured, “And I’m Mark.” Yet somehow, you can’t get enough of it. This first track from Bash Brothers does a masterful job of setting the tone for the epic chronicle one is about to listen to, all brashness and explosions. The piano power chords that form the bedrock of the beat are befitting of two self-involved, ‘roided-out goons on the top of the world. There isn’t quite enough substance to launch this one into the stratosphere, but it’s a perfect curtain-jerker.
Best Lyric: “Freaks hit up my Skytel / I’ll come mess up your Maybelline / My beeper beepin’ more than my dialysis machine / K-k-kidney failure’s just a part of the game / We’re not ashamed, now the world knows my motherfucking name.”
42. “I’m So Humble,” Popstar: Never Stop Never Stopping (2016)
The concept here is a little simple for my tastes, but the execution is flawless. Collaborator Adam Levine returns and backs up Andy / Conner as the latter boasts of how little he likes to boast, and the gentle flow of the rhymes pairs well with the nasal croon of the Maroon 5 frontman. Not as great as some have said, but still above average.
Best Lyric: “I feel more humble than Dikembe Mutombo / After a stumble left him covered in a big pot o’ gumbo.”
41. “We Need Love,” The Wack Album (2013)
The best of the Guy Number One / Guy Number Two songs is, like all of them, interesting for its mishmash of tone: one minute, they’re crooning about how lovely you are; the next, they’re talking about how much your poon smells. Nevertheless, they’re hardly misogynists and are, like all of us, merely trying to find companionship in a harsh world.
Best Lyric: “My ocean’s got motion, but also girth / The closest thing you’ll feel to giving birth.”
40. “After Party,” Turtleneck & Chain (2011)
A saga in the vein of “Like a Boss,” though inferior to that early TLI hit. “After Party” works because of TLI’s gift for escalation — they begin with a man who just wants to have a good time and by the end of the song, well, let’s just say he’s gone on quite a journey. I’m particularly fond of the beat here, which zips and zings along nicely, and the refrain’s vocals from Santigold, an artist who knows the subtle art of sad songs about having a good time.
Best Lyric: “And after that, I meet my totem spirit / It’s a rattlesnake, so I have to kill it / Then I drink all his blood and steal his powers / Slither around in the dirt for hours.”
39. “IHOP Parking Lot,” The Unauthorized Bash Brothers Experience (2019)
God, I wish this song was longer. I suppose it’s always best to leave them wanting more, but one can’t help feeling that an extended round of collaboration between the Haim sisters and the TLI boys would have yielded the ultimate summer funk jam. They get pretty close here in the middle of the track, when it kicks into high gear and you find yourself compelled to dance as though you’re rocking out to a boombox with your best friends on a hot July night. The bassline! The vocals! The presence of Maya Rudolph! (Sure, you can’t really distinguish her voice, but just knowing she’s there is enough.) What’s more, the whole thing very effectively transitions into sexually intimidating entropy, leaving you impressed — albeit still frustrated that you didn’t get to work it more.
Best Lyric: “It’s not phrased weird at all / Shake four halves of butt!”
38. “I Don’t Give a Honk,” The Wack Album (2013)
Much like “Karate Guy,” one wonders where the fuck the concept for “I Don’t Give a Honk” came from. I suppose maybe one of the guys said the phrase “I don’t give a honk” as a gag and another one of them pointed out that you could approach it literally? Whatever, it’s a lot of fun to hear Jorm and Andy go on and on about how much they don’t like bestowing honks on anyone. It’s not quite as good as its spiritual predecessor, “Punch You in the Jeans,” but it’s a delightful effort.
Best Lyric: “Man, I’m stingy when it comes to my honks (me too) / I literally stick ’em to my body with glue.”
37. “Focused AF,” The Unauthorized Bash Brothers Experience (2019)
Perhaps the most upsetting song TLI have ever recorded. “Focused AF” begins ominously enough with twenty seconds of echoing cries and micro-industrial electronics, then transitions into unprompted lyrical confrontation with the listener and strange boasts (“Bash Brothers / Fast lovers / We be fuckin’ faster than chattering teeth”). Then come some clever declarations of friendship and a solemn mutual vow to hit home runs to impress the characters’ fathers. Then it gets really intense. I kind of can’t describe how brilliant it is when Andy / Jose talks about sorrowfully screaming and sodomizing himself with a broom in front of 100 cardboard cutouts of supermodel Kathy Ireland. I can’t even laugh at it. It’s like something out of a goddamn David Lynch movie, that shit. Bravo.
Best Lyric: “I got 100 cardboard cutouts of Kathy Ireland all in one room / I run through that shit naked / Make ’em all watch me fuck myself with a broom / Oh, Kathies; all my Kathies / You’re the only ones that know my pain / And you’re the only ones that see my shame.”
36. “I’m On a Boat,” Incredibad (2009)
Man, remember when this song came out? If I recall correctly, it was so big that Foursquare (man, remember Foursquare?) gave out a badge for anyone who checked in from a boat. The fame was a bit overblown, but not wholly undeserved — this shouted banger about maritime fun somehow captures the thrilling rarity of being on a boat, which was a thing I’d never thought about prior to the song’s release. T-Pain, as is so often the case with him, turns in vox that amaze with their commitment to stupidity.
Best Lyric: “I got my swim trunks and my flippy-floppies / I’m flippin burgers, you at Kinko’s straight flippin’ copies.”
35. “Reba (Two Worlds Collide),” Turtleneck & Chain (2011)
I’ve never understood why “Reba (Two Worlds Collide)” was technically a bonus track on Turtleneck & Chain and subsequently not available on Spotify. It’s a great song, and it works really well as an album-closer! Kenan Thompson is a national treasure and his performance as a guy with a big dick who decided to dress up as Reba McEntire and have sex with Andy is one for the TLI-guest record books. I’m especially into the way Andy simply dismisses any attempt “Reba” makes to correct the record. Love makes fools of us all, I suppose.
Best Lyric: “Flashback to when I first met Reba / Sitcom dressing room, puffing on cheeba /
I said I was a fan; she said, ‘Prove it’ / Dropped her denim skirt and said, ‘Hop to it.’”
34. “Stork Patrol,” Please Incredibad Don’t Hurt ’Em (2005)
A deep, deep, deep cut that deserves a renaissance. “Stork Patrol” dates back to the prehistory of TLI, back when they were called Incredibad, and one longs for the return of conceits as vulgarly outré as this one. A group of dudes go on the prowl to put their dicks in and around storks, and that’s the entire track. Yet, as always, what makes this a TLI song is the attention to detail, exploring every corner and crevice of such an absurd notion. The beat and sample are gnarly as hell, too.
Best Lyric: “What up, Marabou-boo? Don’t I recognize you? / National Geographic cover, ‘92? / Turn around your back; yo, I can barely speak / Oops, there go my kids all over your beak.”
33. “Rock Roll Skate,” Popstar: Never Stop Never Stopping (2016)
Confrontation incarnate. I’m not sure exactly what genre or artist TLI are parodying in “Rock Roll Skate,” but I’m glad they did it. The boys offer no mercy to their foes and listeners in this one, hollering out one of the most disgusting choruses they’ve ever composed, and that’s saying something. Nevertheless, the sheer magnitude of their aggression, combined with the rad, fuzzed-out backing track, makes this one to remember.
Best Lyric: “Kid Brain, bat .280 with the ladies / Every fourth girl I’m gonna crush like crazy.”
32. “Lazy Sunday,” Incredibad (2009)
Although “Lazy Sunday” is the pivot point upon which the entire Lonely Island enterprise turns, it only sorta holds up. Your nostalgia for the time you first saw / heard it in college will make you think it’s one of the best TLI tracks, and yet, it feels amateurish compared to the genius of their later rapped odes to quotidian concerns. That said, it’s still a solid song and Chris Parnell does a great job of passing a comedic torch to Andy. “Lazy Sunday” may not be as titanic as it once was, but “Lazy Scranton”? Still bangs.
Best Lyric: “You can call us Aaron Burr from the way we’re droppin’ Hamiltons.”
31. “Diaper Money,” The Wack Album (2013)
There’s this song in Guys and Dolls called “Fugue for Tinhorns,” in which a trio of gamblers sound off, one by one, about the horses they’re betting on in the latest race. It was all I could think about when I first heard “Diaper Money,” which holds the same essential structure of a trio of dudes talking individually about one topic and eventually tripling up to take us home. The lyrics are so simple and the situations being rapped about so mundane that giggles are mandatory. Andy’s verse, however short, is one of the best-written of his career.
Best Lyric: “Wobbledy-wobbledy-drop into my grave plot / You afraid of death? Well, I’m afraid not.”
30. “The Creep,” Turtleneck & Chain (2011)
God, can you believe how perfect it was that they got John Waters to do the Vincent Price part for this sucker? “The Creep” has a laserlike focus on the execution of its aims, which are to (a) describe the habits of a particular sort of unnerving human and (b) provide a platform for a great Nicki Minaj verse. And, again, I can’t emphasize enough how well Waters does in his brief bookends. Please, lord, let him direct a film starring TLI. You could call it Male Trouble, I guess.
Best Lyric: “But when you sneak into a wake and you see a beefcake / Do the Creep.”
29. “Space Olympics,” Incredibad (2009)
Space opera at its finest. Andy takes charge in this one, wailing about a far-future sporting event gone awry, and his insane performance merges perfectly with the metallic sheen of the backing track. The way he does the little breathy stutter-step when he says “You’re a winner” is worth the price of admission, alone. Like so many TLI songs, it’s hard to say whether anyone knew they needed this sort of thing, but we certainly can’t live without it now.
Best Lyric: “And as I stare death in the face / I know my sins will take me to hell.”
28. “Bikini Babe Workout,” The Unauthorized Bash Brothers Experience (2019)
Maybe I’m missing a real-world reference point involving Mark McGwire and Jose Canseco lifting half-naked women in a gym, but I sorta feel like this song might have originated as a pre-Bash Brothers track. It has no specific character or plot references to the album and just feels like classic TLI: a bizarre, sorta-sexy-except-not premise carried out in excruciating and hilarious detail. The lyrics are specific to the point of being hypnotic — and speaking of hypnotic, the little choral interludes are simply fantastic. Yes, it’s goofy to say bench-pressing women would cause light to shine down, “bathing all in a moment of divinity,” but the idea is expressed with such conviction and Enya-like prowess that it stirs something deep in your soul.
Best Lyric: “A babe walked in and she wanted me to lift her / But she was wearing sweatpants, so I dismissed her / With a good bikini grip, you never risk a blister / Sweatpants slide, that’s a hazard to the lifter.”
27. “We’re Back!” Turtleneck & Chain (2011)
“We started this fake rap shit; the world needs us,” Jorm declares as “We’re Back” cuts out, and he’s not wrong. The absurdity of this ideal album-opener starts at a one, immediately jumps to an 11, and is somewhere in the upper 50s by song’s end. Narrative drift plays a key role here, with the initial stuff about malfunctioning phalluses (which is great on its own!) gradually shading into complete non sequitur boasts about helping the homeless and jerking off to Garfield. God bless.
Best Lyric: “I write freaky fanfiction where cartoons fuck / Got CGI Garfield lickin’ Marmaduke’s nuts.”
26. “I’m a Weirdo,” Popstar: Never Stop Never Stopping (2016)
The most underrated track on Popstar is chockablock with brilliant lines. In addition to the one I cite below, you’ve got “Use a banana as a telephone / use a banana as a telephone,” “I use a Mach3 razor on my beard / I use a Mach10 razor down here / Seven more blades cause I like it sheared,” and “I’m demented and deranged, motherfucker / Choose the middle seat on a plane, motherfucker.” Andy does such a great job of spitting it all out as though all of it is supposed to be impressive or intimidating, and the beat bloops and blorts of the beat are executed with menace. Not one to sleep on.
Best Lyric: “Ay papi, you crazy / Yeah, crazy for driving Miss Daisy / Best picture, must be doin’ somethin’ right / Chicken bit off my dick at a cock fight.”
25. “No Homo” / “No Homo Outro,” Turtleneck & Chain (2011)
We have to talk about homoeroticism in the TLI catalogue. I mean, we’ve already talked about it in this list, but we really have to talk about it in relation to “No Homo.” It’s completely understandable if you think their constant motif of dudes finding pleasure with one another is a form of homophobia, but I’d urge you to reconsider. They genuinely find nothing wrong with homosexual relations and although they delve into tropes about gay culture, they never do so disrespectfully. I mean, the whole idea here is to make fun of people who like sex with men but perform internalized homophobia! What a noble goal! Plus, the Betty Wright sample (also notably used in Beyoncé’s “Upgrade U”) is top-notch, especially in the glorious outro track.
Best Lyric: “Hey yo, I can’t decide who wore it best (no homo) / But I’m feelin’ Diane Keaton’s vest (no homo).”
24. “Hunter the Hungry is Gon’ Eat,” Popstar: Never Stop Never Stopping (2016)
Look, let’s just come out and say it: this ostensible parody of Tyler, the Creator is 100 percent indistinguishable from an actual Tyler, the Creator track. Chris Redd puts in a monster of a performance on this lyrical tour through the hell of one sick mind and the horror-movie production fits oh so well. TLI often go for the gross-out, but they wisely never went this far in their own voices. However, the fact that they can do it is further proof of their genius. The only thing keeping this sucker out of the upper echelons is its unfortunate double use of the word “retarded,” which is understandable, given the object of the parody, but still.
Best Lyric: “Hey yo, I fucked your girl with her baby inside / And then that baby had a baby with rabies and didn’t survive / Think that’s disgusting? Peep this booger I picked / And if you think that’s sick, check this wart on my dick.”
23. “Punch You in the Jeans,” Incredibad (2009)
What I love about “Punch You in the Jeans” is that it just keeps escalating the specificity of how much these two guys hate jeans. Well, they hate them, but they also respect them, as evidenced by the bit where they compliment someone on how good his jeans are by pointing out how much they make them want to punch said jeans. What’s more, the faux-Jurassic 5 beat is a welcome tribute to the Bay Area ’90s milieu in which the boys grew up.
Best Lyric: “Gonna go back in time, find the man who made jeans / And choke him to death, if you know what I mean.”
22. “Fuck Off,” Popstar: Never Stop Never Stopping (2016)
The Disney Channel never knew what hit it. In this eye-widening parody of sugary tween-pop drivel, Andy / Conner exploits the magic of redirected expectations, introducing the song with a verse that is entirely devoid of jokes before jumping to the epically vulgar chorus, darting back again for the second verse, then going even bigger in the subsequent chorus and coda. The melody is perfection and it’s one of those TLI songs where you forget the concept after the 100th play-through and just dig it on its musical merits.
Best Lyric: “Fuck off / ’Cause I might be young / But I’ll dig your grave ’til the job is done.”
21. “The Heist,” Please Incredibad Don’t Hurt ’Em (2005)
This zenith of the proto-TLI songs predicts so much that would come to define the group: rapping about mundanity, celebrating male bonding, and executing surprisingly deft rhymes. We hear a dialogue between two dudes, one of whom just went through a breakup and needs consolation and the other of whom earnestly wants to help his pal get through this tough time. The narrative is clear and heartfelt and the humor comes not from jokes, per se, but rather from your knowledge that none of this really belongs in a hip-hop song, yet feels utterly natural in that environment. By the time you get to the nudity at the end, you can’t help but wish you had friends as genuine as TLI to be there for you when things get rough.
Best Lyric: “I’m pretty broken up, I might not make it there alive / (Don’t talk like that, now you’re makin’ me wanna cry).”
20. “Santana DVX,” Incredibad (2009)
In which the boys celebrate a hometown hero. “Santana DVX,” with its E-40 cameo, is as much a tribute to the Bay Area as it is to the titular champagne, and the enthusiasm with which our heroes present their lyrics is infectious. Sure, it’s silly to pick a vanity champy from Carlos Santana as the official drink of TLI, but they don’t ever really make fun of it, and one comes away feeling like you should pick up a bottle. The galloping beat is a grand old time and hey, if you wanna sample the goods for yourself, be Carlos’s guest.
Best Lyric: “Won hella Grammys, batches throw me they panties / I’m probably your daddy, I probably nutted in your mammy.”
19. “Jizz in My Pants,” Incredibad (2009)
I wish I could go back to the first time I heard this song on SNL, when I didn’t know what the conceit would be. The first verse is ominous, then the literal and figurative abruptness with which the first chorus presents itself is truly hilarious if you have no idea what’s coming. But even if you’ve heard it a million times, “Jizz in My Pants” continues to work exceedingly well with its sinister whispering and pitiful goofiness. I also love how Andy’s character seems to get irritated with his own repeated vocal sample by the end. Poor guys; spontaneous ejaculation can’t be much fun.
Best Lyric: “She turned to me, that’s when she said it / Looked me dead in the face and asked, ‘Cash or credit?’”
18. “Let’s Bash,” The Unauthorized Bash Brothers Experience (2019)
This really oughtta become some baseball player’s entrance music. “Let’s Bash” is everything that people love about the energy of a young athlete, what with its lyrical declarations of physical and attitudinal supremacy and its confidently strutting rhythms. Of course, no athlete will have the balls to adopt it, what with its open admission of steroid use and endorsement of physical violence against the fans of other teams. Oh, and while we’re on the subject of teams: holy shit, that list of every baseball club’s name in the form of boastful puns! That’s gotta be one of the most ambitious verbal challenges the TLI guys have ever embarked upon and, upon doing it, they hit a tater out the stadier, to borrow a phrase.
Best Lyric: “[Litany of team-name puns; too long to include here]”
17. “Finest Girl (Bin Laden Song),” Popstar: Never Stop Never Stopping (2016)
God, what I would give to be in the room when this one got pitched. Why someone would choose to describe a sexual encounter in terms of the illegal and era-ending execution of Osama bin Laden is totally beyond me, but that choice was followed by a flawless execution. It’ll always make one a bit queasy, what with the subject matter, but it all comes together so nicely that it’ll remain in rotation for as long as TLI are remembered by the public. The lyrical shout-out to President Obama is sure to make you wistful, so be prepared.
Best Lyric: “She said, ‘You finished me off, now throw my body in the ocean’ / I yelled, ‘Geronimo’ and took some pictures for postin’.”
16. “Mona Lisa,” Popstar: Never Stop Never Stopping (2016)
TLI-style escalation and surprise at their finest. We begin with Conner bragging about his international travels, then suddenly find ourselves hearing about how unimpressed he was with da Vinci’s most famous work, and ultimately sit through a takedown of said painting that is exquisite in its brutality. The weird part is, I’m kinda with him on this one! Appreciating paintings is hard, man! It sucks when people act like you’re uncultured for being unmoved by them! Say what you will about Conner4Real, but he’s never dishonest with you.
Best Lyric: “You could land a helicopter on that baked-potato forehead / Get this chick some Rogaine / You a bloated corpse, girl.”
15. “Natalie’s Rap,” Incredibad (2009)
Who knew she had it in her? Natalie Portman’s initial turn as a gangsta rapper is one of the best guest appearances in the entire TLI catalog, which is a competitive field to be in. The boasts and attacks are shocking and Portman does a remarkable job of never winking or going too far over the top. It’s all weirdly convincing, and Andy’s crooning cameo at the end takes it from good to great. They should play this shit at Harvard graduations.
Best Lyric: “All the kids looking up to me can suck my dick / Portman, motherfucker; drink ’til I’m sick!”
14. “Threw It on the Ground,” Turtleneck & Chain (2011)
The world is a bad place and we’re confronted every day by enticements and inducements that leave us wondering why we bother to put up with all this bullshit. However, there is one man who dares to fight back. The narrator of “Threw It on the Ground” is a folk hero for his insistence that no one push him around, ask him to do anything, or even be in his presence, really. He is the defiant id, unleashed, and we are lucky to have been in his vocal presence.
Best Lyric: “Man, this ain’t my dad / This is a cell phone!”
13. “Like a Boss,” Incredibad (2009)
TLI didn’t invent the idea of using the phrase “like a boss” in a song. But then again, Jimi Hendrix didn’t write “All Along the Watchtower” — sometimes someone brings an existing idea to its apotheosis. This litany of vignettes about one deeply troubled professional supervisor’s journey to madness and back is another example of the group’s commitment to comedic escalation: we go from “approve memos” to “crash into the sun” and it all feels seamless, somehow. I can’t prove that the titular words became a meme because of TLI, but I’d be disappointed if they didn’t.
Best Lyric: “Call a sex line (like a boss) / Cry deeply (like a boss) / Demand a refund (like a boss).”
12. “Uniform On,” The Unauthorized Bash Brothers Experience (2019)
Sometimes, less is more. The backing track for “Uniform On” is astoundingly simple, consisting primarily of a drum-machine beat and some blips and bloops. But what that really means is there’s nothing distracting you from Andy and Kiv delivering some of the most charismatic and exciting rhyming of their careers. Here are two men in their prime portraying two other men in their prime and basking in the luxurious waters of confidence. There’s nothing high-concept in “Uniform On,” just 106 seconds of pure adrenaline and testosterone injected into your eardrums like ‘roids into a well-sculpted butt.
Best Lyric: “Lift that tire, bitch! / Put your back in it and lift it higher, bitch! / Stab that needle in my ass ’til I am rich! / Make me a god with the chemical sciences!”
11. “Incredible Thoughts,” Popstar: Never Stop Never Stopping (2016)
The high point of Popstar comes near the film’s conclusion, when legendary TLI collaborator Michael Bolton pops up to lend gravitas to this ode to faux-profound idiocy. It’s such a weirdly specific conceit, and yet, as soon as you hear it, you can understand how much it applies to so many situations in which a writer thinks they’re onto something and is, in fact, spouting utter nonsense. Musically, it begins with ominous synth tinkles and elevates itself into arias of blandness, and by the time Justin Timberlake shows up for his uncredited vocal cameo as a talking fish, you’ve fallen utterly in love.
Best Lyric: “A Milk Dud, sitting in the acid rain / A house cat, addicted to the cocaine.”
10. “Spring Break Anthem,” The Wack Album (2013)
It’s entirely possible that I’m ranking this one so high because of my status as a bisexual man. A lesser version of “Spring Break Anthem” would depict three douchey bros who are performing a false heterosexuality as an insecure cover for the fact that they’re secretly gay. But no, these are truly pansexual gents, it seems — they are as into girls baring their breasts as they are into sharing a life with a dude. It’s beautiful, to be honest! And the Skrillex-esque beat makes this a banger about bi men of epic proportions, which is something that can’t be said about literally any other song ever recorded. Hell yeah.
Best Lyric: “Promise to cherish, trust, and respect him / Crushing pussy; marry a man.”
9. “Natalie’s Rap 2.0,” SNL Digital Short (2018)
Much like The Empire Strikes Back, the sequel is an inarguable improvement on the original when it comes to Natalie Portman’s guest appearances on TLI tracks. Although she was charismatic on the original “Natalie’s Rap,” she is stunning as a rapper on “Natalie’s Rap 2.0.” When she brags and attacks here, she almost out-Cardi B’s Cardi B. Real talk, she’s a better rapper here than any of the TLI trio. Her mastery of flow and delivery is nothing short of extraordinary, the beat is sick, and the lyrics are genius. And hey, speaking of Star Wars, any hip-hop track that defends the prequels and glorifies Jar-Jar Binks (and his 17 dicks) is alright by me.
Best Lyric: “They say I’m sex positive / Hell yeah, I’m positive / That you’re going down while I’m bumpin’ ‘My Prerogative.’”
8. “Jack Sparrow,” Turtleneck & Chain (2011)
It’s simply wonderful how Michael Bolton has become a kind of grown-up mentor to the TLI boys, and their wonderful synergy was immediately evident on this first collaboration. A strange and yet entirely comprehensible story-song, it is another example of a track where everything within the narrative goes off the rails but the characters are just so into musical creation that they can’t stop the song and are compelled to incorporate what they’re doing into the text. What’s especially great is that Bolton is right when he croons, “Now back to the good part” and riffs on Pirates of the Caribbean again — the song that the fictional TLI were recording is the worst kind of aggressively sexy male toxicity, and the elder statesman of blue-eyed soul is here to remind us what real passion sounds like.
Best Lyric: “Keira Knightley!”
7. “Boombox,” Incredibad (2009)
I’ve always liked to think “Boombox” is narrated by the same self-satisfied Andy character who sings “Threw It on the Ground.” He’s eternally confident that only he understands how to be cool in a terminally unhip world, isn’t afraid to preach his gospel, and in both cases, he learns an important lesson about going too far with his own philosophy. The racial element is key here, too — the narrator seems to think the very idea of white people dancing can never be cool and we roll our eyes at such hipster bullshit. Also, it’s great that the song, itself, is kinda hard to dance to! It’s so slow and menacing that you can’t imagine getting down too hard with it, but its sonic lusciousness certainly lends itself to some A+ headphone listening.
Best Lyric: “I saw a Spanish guy doing the Bartman.”
6. “Dick in a Box,” Incredibad (2009)
Much like “Lazy Sunday,” “Dick in a Box” isn’t quite as transcendent as you remember it being from the first time you saw / listened to it. Nevertheless, it holds up a ton better than “Lazy Sunday” and is a visionary bit of parody, expertly satirizing the silliness of ’90s R&B crooner groups in a way that would change comedy songwriting forever. “Dick in a Box” is so deeply ingrained in the culture at this point that it’s all too easy to overlook how original the notion of putting one’s phallus in a box is. Who thinks of this shit? You’ll notice that this is the first appearance on the list of the main Justin Timberlake collaborations, and that’s because they all belong in the top 10. Thank you, JT, for helping to start it all here.
Best Lyric: “Backstage at the CMAs / A dick in a box.”
5. “Dreamgirl,” Incredibad (2009)
The best example of narrative drift that TLI have ever recorded. We begin with a promise that we’ll be hearing about the object of someone’s affection, transition into a series of insults uttered with praising earnestness, and — in defiance of sense and causality — wind up with an ad about Chex Mix™. The journey from point A to point B is littered with genius descriptions of a horrifying woman that somehow avoid being misogynist in any way. Perhaps it’s the tone of adoration (the shouts of “I LIKE THAT” are a particularly nice touch) or perhaps it’s the ludicrousness of each trait, but you walk away with your sides aching and your eyes opened to the notion that beauty can be found in anyone and everyone.
Best Lyric: “Last week, thought I saw you on the street / Turns out it was a bag of trash / Just a big, old bag of trash / I thought you looked like a bag of trash.”
4. “3-Way (The Golden Rule),” The Wack Album (2013)
It’s appropriate that this was the culmination (so far) of the Timberlake / Samberg trilogy, as it demonstrates that they were always building up to banging each other. “Here in the dark / It’s hard to tell / Where her body ends / And my homie’s begins” — we laugh at this description of sexual congress, but isn’t there something magical about it? In real life, a menage a trois can be awkward and confusing, but this is its platonic ideal, in which three bodies are conjoined in one conduit of sensual energy. The presence of Lady Gaga, that patron saint of sexual connection, is almost too perfect to be believed.
Best Lyric: “Well, I should diggity-ask you the same.”
3. “YOLO,” The Wack Album (2013)
First of all, let’s talk about the production here: it towers above the listener like an ancient monument, its guitars and drums reverberating through your consciousness. Next, let’s talk about the melody: the boys and Adam Levine introduce us to an earworm that’s almost unparalleled in the TLI catalog. And finally, let’s talk about the most important element of any TLI song, the lyrics: here, we get an anthem for our paranoid times, one in which we are told of how dangerous and intrusive the world has become and how hard it is these days to achieve independence and a fulfilled existence. Andy declares it to be “the battle cry of a generation” and, bizarrely enough, he’s completely right.
Best Lyric: “You know that we are still young / Burn the prints off your thumbs / And pull out all your teeth / So you can’t bite your tongue.”
2. “Motherlover,” Turtleneck & Chain (2011)
By this point, it should have become clear that a lot of TLI songs are about banging. This is entirely understandable for a comedy group, as sex is one of the most fundamentally ridiculous acts a human can engage in. Nevertheless, a person arguably cannot be fully realized until they explore themselves through the indulgence of this most basic biological impulse. We learn about ourselves through sex, and in “Motherlover,” we find two men fumbling toward self-actualization by engaging in copulation with each other’s mothers. Of course, they’re really lusting after their own mothers, though this fact remains blissfully implicit (TLI’s catalog is proof that ribaldry is usually funnier than outright vulgarity, though not always), and although thinking about this universal human perversity is like staring at the sun, we nevertheless are obligated to contemplate it without doing it in real life. What’s more, this is also a song about friendship: “It would be my honor to be your new stepfather,” they tell each other, and the fact that they mean it is something to be treasured.
Best Lyric: “I know just what you mean, my mom’s been so sad and gray / My dad can’t satisfy her in the bedroom ever since he passed away.”
- “I Just Had Sex,” Turtleneck & Chain (2011)
The spoken words that begin “I Just Had Sex” sorta say it all: “Sometimes, something beautiful happens in this world. You don’t know how to express yourself, so you just gotta sing.” In this unbelievably good track, the lads and Akon present an ode to the ineffable wonder of human intimacy, and I’m not being hyperbolic when I say that. Sure, the narrators aren’t the most skilled sexual operators, but that’s sorta the point. They’re inexperienced and being introduced to the idea that someone can make them feel whole for the first time. The words, if taken seriously, are heartfelt prayers of gratitude: “I’m so humbled by a girl’s ability to let me do her,” “Was sure nice of her to let you do that thing / Nice of any girl ever / Now sing,” “If you’re near or far, whether short or tall / We wanna thank you all for letting us fuck you.” When they get to the list of negative traits of the situations in which they bared their bodies and souls, Akon swoops in like an angel to remind them, “Doesn’t matter — had sex.” Yes, the beat is simple, but so is some of the best poetry. In no other TLI track is there such awesome and heartfelt beauty. Bless these boys and the magic they’ve brought us.
Best Lyric: “I’m so humbled by a girl’s ability to let me do her / ’Cause honestly, I’d have sex with a pile of manure / With that in mind, a soft, nice-smelling girl’s better / Plus, she let me wear my chain and my turtleneck sweater.”
