The W S H Black Love Movies of the New Millennium Tournament

15 min readMay 10, 2017

Background

This was initially conceived as an essay dedicated to Love Jones, a movie I’d sorely underrated but have come to increasingly appreciate over the past couple years. Love Jones debuted in theaters on March 14, 1997, in the midst of what I’d argue is a peak in Black cinema. Although this renaissance arguably begins as far back as the late-1980s, the Black romance films of the mid-1990s introduce this extremely wild concept of young, successful, upwardly-mobile African-Americans having the same love issues as, you know, everybody else. Crazy stuff, amirite?

Funny enough, all the movies we’re here to discuss tend to share permutations of the same casts. (Another friendly reminder that Taye Diggs doesn’t seem to love his blackness very much, but will take your Black dollars all the same.) However, the casting similarities alone make comparing and ranking these movies a worthwhile task. Now that we’re in the midst of the NBA Playoffs (also known as “A Boring Prelude for Dubs-Cavs III”), I thought it’d be cool to seed 11 of the most memorable Black romance films of that period and have a tournament of sorts to determine the winner.

Da Rules

Only movies released between 1997 and 2003 are considered. Seedings were given based on each film’s cumulative Rotten Tomatoes score: the average of the movie’s “Tomatometer” and “Audience Score,” as listed on each film’s RT page. The bottom four seeds were placed in a Twitter poll, with the leading vote-getter earning the 8-seed and a spot in the official tournament.

The tournament is single-elimination, and although Rotten Tomatoes provides a subjective foundation for each movie’s seeding, this is otherwise an objective exercise, because these are my personal preferences, and I just so happen to be curator of this here website. Don’t like how this tournament ends? Feel free to print out the bracket and make your own.

(But, seriously, do your own brackets and share them with me on Twitter. It’ll be cool to see the differences in opinion and whatnot.)

**Da Movies (listed in order of seeding*)**

(1) Love & Basketball (88.5 cumulative rating): “Quincy and Monica grew up in the same neighborhood and have known each other since childhood. As they grow into adulthood, they fall in love, but they also share another all-consuming passion: basketball. … As Quincy and Monica struggle to make their relationship work, they follow separate career paths through high school and college basketball and, they hope, into stardom in big-league professional ball.”

(2) Love Jones (82): “Darius is a novelist who is giving a reading at the Sanctuary. … Shortly before his set, he meets Nina, a woman who is a gifted photographer, despite the fact that she just lost her job. … A mutual attraction is sparked between them; but neither Darius or Nina are sure where to go next after this promising start.”

(3) Baby Boy (79): “Tyrese Gibson stars as Jody, a jobless 20-year-old African-American man who has fathered two children by two different women, Yvette and Peanut, although he still lives with his 36-year-old mother Juanita. As Jody grapples with the increasing pressures of adult responsibility, he also contends with his troubled best friend Sweetpea and new adversary Rodney. Then there’s his mother’s live-in boyfriend Marvin, a reformed gangsta who agrees with Juanita that her son should grow up, move out, and move on.”

(4) The Best Man (79): “Harper is an author whose first novel is soon to be published, just as he’s been asked to be Best Man at the wedding of his friends Lance and Mia. Harper is suffering a worse case of publication-day jitters than most authors, and with good reason: much of his book has been drawn from real life, and he’s afraid that his friends and family will spot the sometimes unflattering literary versions of themselves. What’s worse, Mia and Harper had a fling years ago, and their affair made it into the book; Lance doesn’t know, and Harper would just as soon he didn’t find out before the wedding.”

(5) Brown Sugar (78): “Dre and Sidney became best friends when they were ten years old — the same time that both first became aware of the first rumblings of the Hip Hop revolution in New York City. Today, Dre runs a successful record label, and Sidney is a respected music journalist; both have managed to turn their love for the music into careers, and both are still close friends. Close enough, in fact, that many of their pals wonder why they’ve never become boyfriend and girlfriend.”

(6) The Wood (76.5): “Roland is a few hours away from getting married, and he is starting to have second thoughts; as much as he loves his fiancée, he can’t stop thinking about Tanya, his first serious girlfriend in high school. Roland is hanging out with his two best friends, whom he also first met in school, Mike and Slim. They talk about the old days and flash back on growing up in Inglewood, California in the 1980’s … At the last minute, Roland takes off, wanting to pay Tanya a visit, and Mike and Slim are determined to track him down and make sure that he gets to the altar on time.”

(7) The Brothers (74.5): “Terry, Jackson, Brian, and Derrick are four close friends who get together once a week to play basketball and compare notes on their problems with women. And as it turns out, they have a lot to say in that area. Terry has just gotten engaged to BeBe, who is more than a bit controlling. Jackson has a deep fear of commitment, symbolized by a recurring dream in which he’s attacked by women wearing wedding gowns; what’s more, he’s started seeing Denise, who he learns once had a fling with his dad. Brian is a lawyer who has discovered his next court date will see him pleading a case in front of a judge who used to be his girlfriend. And Derrick’s marriage to Sheila is falling apart at the seams.”

(8) Two Can Play That Game (63.5): “Vivica A. Fox stars as Shante, a knowledgeable veteran of the dating game who thinks she’s found the perfect mate in the handsome Keith. When Keith is spotted stepping out with Shante’s arch-rival Conny, the spurned lover institutes what she labels the ‘ten-day plan,’ an all-out assault on Keith designed to make him come crawling back to her.”

(9) Deliver Us from Eva (60): “Eva Dandridge developed a sense of responsibility early on in life, when after the death of her parents she was left to care for her three younger sisters, Kareenah, Bethany, and Jacqui. All four of the Dandridge sisters have grown up to be attractive, intelligent, and successful; Kareenah is happily married to Tim, while Bethany is engaged to Michael, and Jacqui is going steady with Darrell. However, Eva still watches over her siblings like a hawk, and while her sisters love Eva dearly, Tim, Michael, and Darrell wish their sister-in-law would stay out of their business. The guys decide that if Eva had a boyfriend, she might be less interested in running other people’s lives, and they turn to Ray, a notorious ladies’ man, for help.”

(10) How Stella Got Her Groove Back (57.5): “San Francisco stockbroker Stella, a 40-year-old divorcee, has a nice Marin County home and an 11-year-old son, Quincy. With Quincy off to see his dad, Stella and her best friend Delilah vacation in Jamaica, where she meets sexy, good-looking Winston Shakespeare. He’s the man of her dreams in every way except one — he’s half her age.”

(11) Def Jam’s How to Be a Player (45): “When it comes to loving women, Drayton Jackson is a real player, at least when his girlfriend Lisa isn’t around. He is assisted in his quest for more girls by his buddies Kilo and Spootie and by his love-lorn cousin David. Appalled, but somewhat fascinated by her brother’s secret avocation, Dray’s sister Jenny and her sweet girlfriend Katrina decide to study his life-style for their anthropology class. They also start trying to scam him into cleaning up his act by tricking him into attending a special party in Malibu.”

(*although Baby Boy and The Best Man tie for the 3-seed, Baby Boy earns the 3-seed by virtue of alphabetical order. Besides, methinks The Best Man at 4 makes for an interesting quarterfinals matchup.)

Da Twitter Poll

The Twitter poll, which ran from Wednesday, April 26 through Sunday, April 30, allowed folks to vote for their favorite amongst the four lowest seeds (Two Can Play That Game, Deliver Us from Eva, How Stella Got Her Groove Back, and How to Be a Player). Much appreciation to the 51 participants and anyone else who retweeted the poll or told some friends to cast some votes.

By virtue of its Twitter victory (ha!), Deliver Us from Eva earns a spot in the tournament, where it’ll go head-to-head with overall 1-seed Love & Basketball.

Da Quarterfinals

(1) Love & Basketball vs. (9) Deliver Us from Eva

I’m assuming you all have listened to the podcast by now. (If you haven’t, here’s the SoundCloud link for your convenience.)

If you haven’t listened yet, I can’t avoid this spoiler, so apologies in advance. But Deliver Us from Eva won this matchup. Which is patently absurd, but I was outvoted, and I believe in a fair vote and a democratic process, so it is what is is.

I say this as one who believes Love & Basketball is super overrated AND the one who plotted on getting Deliver Us from Eva in this tournament in the first place: there is absolutely no chance Eva is better than Love & Basketball. Do I enjoy Eva more? Sure. If Eva and Love & Basketball were on at the same time, would I have a hard time picking which one to watch? Probably. That doesn’t mean I can convincingly argue Eva deserves to advance.

Love & Basketball can be super corny and has a few easy-to-spot plot holes, but Deliver Us from Eva just isn’t good. “Enjoyable” and “good” are mutually exclusive concepts. Eva has too many beauty salon scenes, too much Kym Whitley, a scene where “I can bench-press your house and squat your car” LL Cool J gets successfully kidnapped by 3 guys I’m not sure could kidnap me … I’m not buying it. Issa no from me, dog.

(Don’t worry, the Love & Basketball evisceration comes next round, guys. Stay tuned.)

(2) Love Jones vs. (7) The Brothers

I’ll admit it, I like The Brothers. But is the storyline hella problematic? Definitely. Bill Bellamy swears he won’t date black women again. D.L. Hughley might divorce his wife because she finds fellatio disgusting. Morris Chestnut somehow (?!) begins dating the same woman who once dated his father. What are the odds? I shake my head at like 80% of that movie, and that might be a low estimate.

Love Jones wins this matchup going away, and I don’t really feel compelled to explain why, considering I’m sure the majority of you have watched both these movies and have come to the same conclusion. But The Brothers is another one of those bad, enjoyable movies. I enjoy seeing 4 successful black men, regardless of how ridiculous their lives in storyline may be. It’s silly, and it’s fun, and it has Tatyana Ali. But I’d never pretend that it’s better than Love Jones, because it’s not. Next matchup.

(3) Baby Boy vs. (6) The Wood

This is my second-favorite matchup of the first round. Prepare for the first official hot take of this article, because this right here might make some folks mad.

Okay.

Ready?

(… I don’t really like The Wood.)

Okay, that might be overstating it. I’ve always liked it, I suppose. It’s a cool movie, and definitely one of the better movies in this field. But I’ve never been able to devote my full attention to it while it’s playing. I mean, The Wood wins the tournament, according to the podcast, and fairly easily, too. I watched it the other day after we recorded the podcast, wondering if I’d missed … something.

I fell asleep.

I woke up maybe 45 minutes later, fully cognizant of what scene was on, but definitely not pressed to rewind it or start the movie over. And I guess that explains my relationship with the movie: it’s always been akin to good background noise to me, a movie I can turn on while doing chores or some homework. I might take a break and peek at the television and laugh, but rarely do I just want to sit down and watch that movie. Any time I make that the goal, I fall asleep. Just like I did the other day.

So, I mean, Baby Boy could win.

It won’t, of course, but I’d be willing to entertain the argument.

I hadn’t seen Baby Boy until maybe my sophomore year of college, simply because I can’t stand Tyrese. (Seriously, we either have to stop giving him platforms on which to sound ridiculous or trade him in the next racial draft. Word to Chappelle.) Despite my distaste for all things Jody, I really really like that movie. It’s real-life hilarious, but I feel like we all know or know of somebody living like Jody and Yvette. I like movies that allow you to root for the bad guy, because Jody isn’t really bad, per se. He’s just really dumb. He needs to grow up, and once he begins that process, all of life’s problems don’t magically disappear, but he’s much better equipped to, you know, handle them.

As I write this, I’m beginning to reconsider this round’s winner, but despite my personal preferences, I know The Wood is better. Let me state one more time, for the record, I do not hate The Wood. I just wish I could watch it from start-to-finish. I don’t feel like that’s wrong to ask. Let’s move on before I change my mind.

(4) The Best Man vs. (5) Brown Sugar

Sorry, Donny.

Like nine months ago, this tournament doesn’t happen, because The Best Man comes in as the undefeated, dominant 1-seed who wins every matchup by like 25 points.

However, I’ve since had a change of heart.

If this tournament were based on watchability alone, Best Man still wins comfortably. But that movie is so flawed. So very flawed. Allow me to count the ways:

No caring, generous, responsible Best Man writes this book even remotely close to the wedding.
Nobody in this friend group is a decent human being? Really? (I guess Murch is the exception, but he a) can’t keep a secret, and b) seems exceptionally spineless. So, yeah.)
Harper Stewart, the aforementioned Best Man responsible for the movie’s debacle, completely disregards Nia Long’s Jordan Armstrong in full lingerie because his feelings are hurt. Mind you, he’s the reason for 97% of the problems in this movie.

I’ll stop there. But, come on. Problem #4 is that the wedding definitely doesn’t happen the day after Morris Chestnut’s character discovers his soon-to-be-wife cheated on him with his best friend, but I’ll let that one slide only because I guess it’s possible. Like 19% possible, but possible all the same.

Yeah, this movie can’t win. I have much more to say about Brown Sugar, but “when did you fall in love with hip-hop” is all it needs to advance right now.

Dang, Best Man. Can’t come stumbling into the playoffs. That’s how you get upset.

WHAT’S NEXT?

Da Semifinals

(1) Love & Basketball vs. (5) Brown Sugar

Before the podcast, I never noticed the similarities between the two. Although one is centered around basketball (obviously) and the other around hip-hop, they’re both stories rooted in childhood, where a boy and girl forge deep ties due to their love of the same thing. And Sanaa Lathan plays the female lead in both, so there’s that.

Nonetheless, Brown Sugar is a superior movie, in so many ways. Love & Basketball ends with so many unanswered questions. You mean to tell me Quincy and Monica never had sex until the night Monica got her USC offer? I’m really supposed to believe Q committed to Monica months before becoming a star — a freshman star! — at USC? Monica really kept holding out hope for Q even though he definitely wasn’t waiting around for her? “Double or nothing?” Word?

Quincy does Monica bold THE ENTIRE MOVIE, and they still wind up married with a kid. I suppose. At least she gets the upper hand at the end of the movie, with her basketball career still flourishing while he’s forced to play the dutiful husband and father, if you’d call that getting the upper hand. (Side note: I’m fairly certain Monica moving back to Los Angeles to play in the WNBA was supposed to be triumphant, right? I feel like that league is in way worse shape today than it was in 2000, but that’s a topic for another article that I’ll likely never write. Shoutout to the Detroit Shock, though.)

Brown Sugar tells a more believable story. Like the good brother William says on last week’s podcast, it uses hip-hop as something of a conduit. I’m sure we all have the friend we share music with, who loves rap music just as much, if not more. They spend essentially their entire lives pretending their shared love of hip-hop hasn’t formed a mutual admiration, a desire to discover if something else could exist, but their friendship remains the foundation upon which the relationship is built. Both movies end happily — and maybe even a bit contrived — but at least Brown Sugar’s ending is heartwarming. Love & Basketball leaves me wondering why Monica was ever so drawn to Quincy to begin with.

It pains me that I’m essentially choosing Taye Diggs over Omar Epps, but there’s nothing I can do. Brown Sugar moves on to the championship round.

(2) Love Jones vs. The Wood

I’ve already said my piece on The Wood. Let’s move on. Love Jones advances.

Da Championship

(2) Love Jones vs. (5) Brown Sugar

Coincidentally (or maybe not), these are my two favorite movies of the bunch. And, to be honest, I still haven’t picked a winner. So let’s sort this out.

Love Jones is … stunning. I think that’s the most appropriate word. I think I like it so much, especially right now, because of my ability to relate to the storyline. These two beautiful mid-20s black hipsters with their cool clothes and cool music and jazz clubs who are kind-of just feeling their way through this phase of their lives … it’s a really good hook. Once upon a time, I didn’t like Love Jones, either. I didn’t really get the point. Over time, I’ve come to understand that movie only works if you’ve personally experienced the feelings it tries to evoke. And although some might argue that not everyone encounters that type of love, I’d vehemently disagree. All of these movies are about a “love jones,” in one way or another. Monica can’t shake Q; Yvette can’t shake Jody; apparently none of the women in The Best Man can shake Harper. Love Jones just deals with that dilemma without any of the pretense, I think.

Brown Sugar is definitely funnier, but it somehow manages to be cornier and hokier than the movie explicitly about black hipster love. This is the fate of the romantic comedy in general: some jokes fall flat, some lines don’t age as well as the writers would have liked. I do think Brown Sugar is insulated from these complaints far better than the rest of the romantic comedies listed, if only because “when did you fall in love with hip-hop?” is a pertinent question still asked on the Twitters and the broader internets. But its predictability serves as its downfall in this matchup. In hindsight, it’s fairly easy to assume both couples wind up together, but Brown Sugar feels like it’s building to that point in a way Love Jones doesn’t. Both Nia Long and Larenz Tate’s characters are remarkably flighty and flaky; a hypothetical Love Jones sequel could pick up 3 weeks later with them not speaking again, and I wouldn’t be surprised at all.

I don’t know. I’ll give the nod to Love Jones, but someone could give me a 15-minute lecture on why Brown Sugar is better, and I wouldn’t ask that person to leave me alone.