At the dawn of a new era for hip-hop and rom-coms, Brown Sugar hit all the right notes

There are two standout sequences in the 2002 romantic comedy Brown Sugar. The first is a sleekly edited opening prologue that features rappers like Kool G Rap, Talib Kweli, Common, Questlove, and Method Man explaining when they first fell in love with hip-hop. We’ll later learn it’s the question that music journalist Sidney Shaw (Sanaa Lathan) asks all her interview subjects. But here it serves as a cinematic statement of purpose: Hip-hop isn’t just a backdrop for the film, it’s part of its lifeblood. And while Brown Sugar warmly invites all of its viewers to fall in love with the music, it isn’t here to school its audience. Instead it’s a love letter to those who already adore the genre.

The other standout sequence is a nine-minute dialogue scene in which the film’s six main players swirl around each other during a slightly tipsy New Year’s Eve party. As the characters move back and forth between the kitchen and the dining room, they keep rearranging themselves in new two-person combos to vent, gossip, flirt, and fight—sometimes all at the same time. It’s the sort of funny, cleverly staged character-centric action that romantic comedies do best. If Brown Sugar’s prologue is rooted in the specificity of hip-hop, the party scene artfully deploys the sort of subtle verbal and physical comedy that has fueled the rom-com genre going all the way back to the 1930s.

Both sequences speak to the unique perspective of director Rick Famuyiwa, an under-appreciated auteur. The son of Nigerian immigrant parents, Famuyiwa has been interested in blending the specific with the universal going all the way back to his 1996 student film, “Blacktop Lingo,” which earned him a spot at the Sundance Filmmaker’s Institute. These days, Famuyiwa is best known for his work as a writer and director on The Mandolorian (as well as his brief connection to The Flash movie). But his film career is defined by two semi-autobiographical Inglewood-set coming-of-age stories: 1999’s The Wood and 2015’s Dope. Both redefined the Black teen film for their respective eras. And in between them, Famuyiwa tried his hand at bringing some of that same originality to the world of studio rom-coms.

“Love stories happen in communities outside of just the Upper West Side of Manhattan,” Famuyiwa explained around Brown Sugar’s 15th anniversary. “I loved films like When Harry Met Sally and Annie Hall, but these were very specific, white Manhattan experiences. You don’t see a single person of color anywhere, but somehow these films are universal.” Brown Sugar—which was one of the first films to shoot on location in New York City after 9/11—offers its own take on the New York rom-com template, one anchored around Brooklyn and the Bronx and scored by generations of hip-hop artists. Famuyiwa wanted to bring out the romanticism of a musical genre that was becoming increasingly associated with violence and excess in its mainstream commercial form.

The sometimes-clunky central conceit of Brown Sugar is that the evolution of hip-hop mirrors the evolving dynamic between lifelong friends Sidney and Dre (Taye Diggs). “Hip-hop was as young, naive, confused, sometimes innocent, and sometimes as mischievous as I was,” Sidney narrates as she reflects back on the summer of 1984, when she and Dre were kids watching Slick Rick, Dana Dane, and Doug E. Fresh battle in the Bronx. It was the birth of the golden age of hip-hop, and it inspired Sidney and Dre to pursue their own careers in the burgeoning industry. By 2002, she’s the newly hired editor-in-chief of XXL magazine, and he’s an A&R exec for Millennium Records. Through it all, they’ve maintained the sort of close-knit best friendship that tends to make the people they date slightly wary. But as hip-hop finds itself at a crossroads, so do Sidney and Dre. His engagement to elegant attorney Reese (Nicole Ari Parker) puts a ticking time clock on their unresolved sexual tension.

Though Famuyiwa has a co-writing credit on Brown Sugar, the idea for the project came from screenwriter Michael Elliot, who took inspiration from a Mary J. Blige song. In “Seven Days,” Blige sings, “I never thought we would be together / I can’t believe I just made love to you / After all the things that we’ve been through / Now what are we gonna do?” Elliot thought the story of two lifelong friends navigating the sometimes blurry line between platonic and romantic love would make for a compelling film. Plus, it came with a ready-made elevator pitch: When Harry Met Sally in the world of hip-hop.

As with so many of our most iconic rom-com pairings, there’s a meta comfort to seeing Diggs and Lathan reunite in Brown Sugar. In addition to working with Famuyiwa on The Wood, they’d previously played lovers in 1999’s The Best Man, which was a cornerstone of the Black rom-com boom of the late ’90s. And they’d each had their own individual successes in the rom-com genre, too. Diggs first burst onto the scene as the Jamaican heartthrob in How Stella Got Her Groove Back, while Lathan helped redefine romantic dramas in the stellar Love & Basketball—a film that shares more than a little DNA with Brown Sugar.

Though Brown Sugar doesn’t reach the sky-high heights of Love & Basketball or When Harry Met Sally, it’s still a really solid early 2000s rom-com—one that leans into the comedic side of the genre while still feeling grounded. Diggs, in particular, gets to be more relaxed and goofy than in his previous rom-com work; for all his reputation as a suave sex symbol, he knows how to pull a funny face like an old-school vaudevillian, and Brown Sugar takes full advantage of that. Especially when it pairs him with a gimmicky rap group called Ren & Ten, the Hip-Hop Dalmatians. A Black and white duo aiming for “that whole unity thing,” their first single is a cover of the Michael Jackson/Paul McCartney duet “The Girl Is Mine” they’ve redubbed “The Ho Is Mine.” Famuyiwa loves hip-hop enough to know just how to poke fun at its foibles.

But the real measure of Brown Sugar’s success is how thoughtfully Famuyiwa treats his supporting characters, which is often what separates a mediocre rom-com from a good one. Instead of writing off Dre’s fiancée as a villain, Brown Sugar makes a point of humanizing her, even after she proves less than loyal. Elsewhere, Queen Latifah makes a funny but grounded impression as Sidney’s no-nonsense cousin Francine, so much so that Elliot would later write an entire rom-com vehicle for her in 2010’s Just Wright. And Boris Kodjoe is equally fun as an NBA player trying to launch a rap career.

But the film’s biggest scene-stealing turn comes from Yasiin Bey, then still going by Mos Def, who plays the talented emcee and part-time cab driver who inspires Dre to quit his job at Millennium and start his own record company. As Chris, Bey gives a god-level rom-com best friend performance, one that’s winkingly self-aware about how it fits into the narrative. “I’m not the Humphrey Bogart in this,” he tells Dre at one point. “I’m the Peter Lorre. I’m the sidekick character. You’re the Humphrey Bogart.” The real-life rapper brings a quirkily breezy naturalism to his role as a self-possessed artist who has no interest in selling out. (He also performs the film’s title track, which was produced by a young Kanye West.) Chris provides a crucial contrast to the film’s satirical jabs at the Hip-Hop Dalmatians. But he also feels like a fully three-dimensional character in his own right, one who’s as confident about his craft as he is nervous to ask out Latifah’s Francine. In a just world, we would’ve gotten a whole spinoff film about the two of them.

Chris is also key to Brown Sugar’s central (and painfully unsubtle) theme about authenticity and integrity. What’s the best way to evolve while staying true to yourself? Is it by innovating in a new direction or trying to recapture the past? It was the question facing hip-hop as it headed into the 21st century and also the problem facing Sidney and Dre as they head into their 30s. And just in case we missed it, the film makes sure to drive that point home over and over again via Sidney’s metaphor-heavy voice over: “I always thought one day I would outgrow my relationship with hip-hop. I never thought it was a fad, like many. But I never thought it could grow and mature.”

Brown Sugar sort of gets away with the lack of subtlety because Sidney’s flowery narration is supposed to be from a book she’s writing. In fact, Ravynn K. Stringfield has written beautifully about how Brown Sugar functions as an ode to the long lineage of Black women writers: “Given that writing is often Sid’s fullest expression of self, it’s important for her to be read. To be read is to be seen, to be heard, and to be understood.” When Dre casually quotes one of her articles to her, Sidney realizes he sees her in a way no one else does. “You are the perfect verse over a tight beat,” Dre tells her at one point. A love of hip-hop requires a love of words, and Sidney and Dre have an endless supply of that.

Though Brown Sugar was a solid box office success, it took Famuyiwa eight years to direct his next film—and not for his lack of trying. “I’m not Terrence Malick, waiting around for inspiration,” Famuyiwa explained of his long gap between projects. “As a Black man working in the business, it’s a challenge sometimes to get some of these things and these stories told when they don’t quite fit in a box or convention of what people expect of you or what you should be telling.” He dove back into the rom-com genre to diminishing returns with 2010’s Our Family Wedding, an interracial romance that succumbs to the worst, most pained excesses of that era of studio rom-com filmmaking. In fact, the frustrating experience is what inspired Famuyiwa to return to his indie roots with Dope. “I felt like I had gotten so far away from my original voice,” he told Buzzfeed.

With Brown Sugar, Famuyiwa found a way to inject his voice into a familiar formula. Between the unique hip-hop premise and the film’s overall buoyant tone, Brown Sugar is a rom-com with real personality and originality, something the genre was increasingly in need of as the highs of the ’90s rom-com renaissance started to curdle into the excesses of the 2000s. In other words, Brown Sugar is a mainstream rom-com that doesn’t sell out. And that’s something Famuyiwa’s characters would surely be proud of.

Next time: Forget your troubles, come on get happy with Judy Garland and Gene Kelly in 1950’s Summer Stock.