My 11th Grade Sad Bastard Playlist

In my junior year of high school (2000–2001) I was moody, lovelorn, pathetic and dedicated to making embarrassing emotion-specific mix CDs. This year on Valentine’s Day I’ve decided to compile a playlist as I look back with horror, shame, & a little fondness on some of the best cuts from my sadness era. This is a typical (but certainly not comprehensive) list of my favorite 11th grade depression jamz.

1. Staind — It’s Been A While

You know, I’m not even ashamed of this one anymore. I’ll own it. I loved this song. I listened to it every day for weeks in 2001. I thoroughly internalized the lyrics and thought they were practically about me, even though at the time I wasn’t actually addicted to anything nor had I dated or been dumped by anyone yet.

Looking back I see that it went to # 5 on the Billboard Hot 100 so yeah, not just for me. I’ll also admit this song came out just before I heard of Napster, thus making Staind’s Break The Cycle the last album I ever bought specifically to hear one song. I did this at the Newbury Comics in the Burlington Mall while staying the weekend on the Brandeis campus for some sort of junior achievement mock-CEO business retreat. Later that night my roommate asked me point blank if I’d bought it just for the hit and I lied and said “Nah, I’m pretty into Staind”. Yes, you’ve read that correctly. I’m confessing to you now that I was the only person in history to ever lie about being more of a Staind fan than they actually were. I want you to know that I tried really really hard for a week to be pretty into Staind, but my nu-metal heart belonged to Limp Bizkit.

2 . Alice In Chains — Nutshell

I’ve never felt more sorry for myself than listening to this song in a theatrically darkened bedroom on Friday nights in high school. It was the song I had on repeat during junior year prom night when I stayed at home filling out info-request cards for colleges because the girl I wanted to take was going with my best friend instead (such drama!).

I’ll note that between the jagged body waves of grief I was taking way too much pride in having created a new Hotmail account with my real name that afternoon as it would most definitely give me a leg up in the application process over the aliased AOL handle I’d been using since 7th grade.

Make no mistake, this song exists so that you the listener can rest doubtless in your conviction that no miserable soul in history has ever felt such sorrow as that which you carry. Best of all, it makes you feel OK about all of the self-pitying navel gazing by easing you into it. The first few lines tell you that “WE chase misprinted lies / WE face the path of time” See? You’re an empathetic person that recognizes the (admittedly less-intense) pain of others. Then cuts the BS and gives you exactly what you came for: “And yet I fight, and yet I fight this battle all alone/ no one to cry to, no one to call home” Beautiful. And I use that Hotmail account as a burner to this day - some things really last…

3. Thomas Newman — American Beauty — Plastic Bag Theme

Yes. I admit it. I was enough of a wannabe artistic high school piece of shit that I put the backing track for maybe the most parodied scene in millennium-era cinema on not one but several of my sadboy mix CDs. I’m still trying to atone.

I remember watching American Beauty for the first time. It was kind of a formative weekend as I’d convinced my mom to rent both it and Fight Club on VHS from Knapp Video in the next town over. While Fight Club supplied me with AIM away message quotes for years to come it was American Beauty that was the more emotionally resonant. Also I ended up watching it with mom. About halfway through the scene (where angsty teen Ricky presents a 15 minute video of a windblown plastic bag to angsty teen Jane as “the most beautiful thing I’ve ever filmed”, thus sealing their burgeoning love) my mom turned away from the screen, looked me in the eye, and said “Wes…just so you know…no girl would be attracted by something like this. Don’t ever try this.”

Well, TOO LATE MA! By that point I already thought it was the most badass thing ever. AND the actor playing Ricky was also named Wes…so there was no turning back.

I’d like to formally apologize to every girl I ever showed my “deep” and “misunderstood” photography to in an inept attempt at seduction.

4. Jimi Hendrix — Little Wing

Jimi Hendrix: The Ultimate Experience was the very first CD I ever owned personally. I’d had a decently extensive cassette collection before that, consisting mainly of mixtapes I’d cobbled together from the radio and my mom’s CDs (with pride of place belonging to the Saturday Night Fever soundtrack that my aunt Erica had gotten for me in 6th grade after much begging). But on Christmas day in 7th grade my dad rolled through and blessed me with some Jimi on disc. Felt like I was in the big time. I started off loving the most driving & energetic stuff: All Along the Watchtower, Purple Haze, The Star Spangled Banner from Woodstock, etc. But as I grew into my utterly routine high school sadness I came to love the tracks that burned slow. By then I’d discovered the wordless Olympic Studios version of Little Wing on the Jimi Hendrix Experience box set and I played more weeping air guitar to this track than I can ever tell you.

Me being uncharacteristically happy for the period. Sporting my then standard uniform of cargo pants & a polo shirt. Also, I had a thing about saving empty water bottles in my locker…

5. Red House Painters — Medicine Bottle

This is what you’re getting if you put a gun to my head and demand the most depressing song I can think of. I want to call it an avalanche of melancholy but avalanche is a bit too intense . This is more like a babbling brook of melancholy, an isolated regret-filled babbling brook that flows straight from Hades with the tears of the damned. If you’re going to listen to this you should probably write down some long term goals, hide your sharp objects, and think of the best friend you have who likes to listen, you’ll want to call them soon. This was a late night staple. With an impressive track length of nearly ten minutes I could dim the lights, roll into a ball, put my depression mix CD on repeat and hear the line blood dripping from the bed to a neatly written poem six times in an hour without having to lift my head off a tear-spotted pillow. Good times.

6. Apocalyptica — Fade to Black

Nothing is going to make you feel like a sophisticated & fashionably depressed 17 year old artisté like listening to the saddest song by one of the most iconic metal bands ever…as performed by a group of classically trained cellists. The “I bet no one else even knows about this” factor was strong with this one, but of course many many other people did know about this since I’d heard about it from at least 2 different classmates in the back row of trigonometry class.

Don’t get me wrong, I thoroughly enjoyed and was equally depressed to Metallica’s album version. It just felt more palpably sad to belt the lyrics myself over the strings cover version in the cool glow of the Lava Lamp my mom got me for my birthday. That’s what Rimbaud would have done.

7. Jon Secada — Just Another Day

Aww yeah, this song managed to bridge two periods of heartache a decade apart from each other. I clearly remember the first time I heard it: a Friday night in 1992 while in my mom’s car as we drove back to the suburbs from Boston (I think we’d gone in so she could by black haircare & beauty products because it was 1992 and aisle nine of the Stoughton, MA Osco Drug wouldn’t get stocked with Luster’s Pink Oil Moisturizer Hair Lotion for at least another decade).

I was as much in love then as it’s possible for an 8 year old to be, but alas, C.G. Hughes didn’t know I existed. That was fairly impressive in school which had maybe forty 3rd graders who saw each other every day. And I’m only pretty sure her name was C.G. Hughes, it’s been a few decades, but she definitely peed her pants at indoor recess one day that year and while most of the other kids ruthlessly ripped on her I promised myself that if I were her boyfriend I’d make it all OK.

That never happened, but as I stared into the headlights on the opposite side of I-93 with my head pressed against the window I heard Secada’s gift to the human race, and for five and a half minutes in the back of a Toyota Corolla I stopped worrying about getting home in time for TGIF and realized what it truly meant to yearn for the unattainable…

The song was really hot for a few months and eventually grew to became a standard on the type of adult contemporary programming where latenight lonelyhearts still call in requests dedicated to long-distance flames, but it wasn’t until illegal file sharing became big that I was really able to hear it much again. I think it was one of the first 20 songs I ever got off Napster and I appreciated being able to hurt to it with almost another decade of “life experience” under my belt.

8. Blink 182 — Adam’s Song

I was a sad high school kid in a mostly white suburb at the turn of the millennium. What can I say? This shit was gospel. Oh the hours I spent thinking of how bad all the people who never understood me would feel about themselves at my funeral… You live, you learn, you go to college and discover Wu-Tang, EDM, & post-rock, we’ve been there.

9. Bonnie Raitt — I Can’t Make You Love Me

When I was feeling the specific suburban-divorcee-blitzed-on-white-zinfandel strain of depression my go to tracks were this and Dido’s Thank You but I’d been listening to this for much longer so it usually won out. The album version from Luck of the Draw is an undisputed classic but I’d downloaded an mp3 of the live version from the 1992 Grammys and yeah, I’ll admit I wept to it on multiple occasions. Feels good to get that off my chest.

10. Pearl Jam — Black

Looking back at this one I’m kind of torn. On one hand it’s a raw & perfect embodiment of post-breakup despair. On the other I simply have no doubt that this has been the anthem of legions of “can’t-let-it-go” stalkers since grunge’s heyday. There’s plaintive and then there’s ominously plaintive and considering this track shows up right before Jeremy on the Ten LP I think we can guess which way it tilts.

Once, on the bus home from school, my Sony Discman played this twice in a row while on random. I knew then that my pain was special & unique.

11. The Spinners — I’ll Be Around

This is on my top 50 desert island all-time playlist. I grew up hearing this at cookouts, family reunions, and in the Buicks, Cadillacs, & Oldsmobiles of my uncles and I’ve never stopped hanging on every note during every listen. The smoothest vocals, that guitar riff, sadness with dignity, resignation with a little bit of hope, it is perfect. If you feel the need to lip sync serenade your mirror but you’re stuck on what song to pick I assure you that this is a worthy selection on all occasions. Bonus points if you develop your own version of the choreography seen in their Soul Train video.