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When Romance Met ComedyWhen Romance Met ComedyWith When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

From the late ’90s to the mid 2010s, Sanaa Lathan and Taye Diggs starred in five major romantic comedies, two of them opposite one another. Yet when people rattle off lists of the genre’s biggest stars, their names seldom appear alongside rom-com players like Kate Hudson and Hugh Grant. That’s partially because the films they starred in (Brown Sugar, Love & Basketball, and How Stella Got Her Groove Back, among others) made less money and had less widespread cultural impact than the biggest rom-coms of the era. But both of those things are also tied into the pervasive cultural segregation of the romantic comedy genre and how it’s marketed. Films about white people falling in love are considered rom-coms. Films about black people falling in love are considered “black movies.”

It’s an idea cultural critic Soraya Roberts explored in her 2018 Long Reads essay “RonCon: Our Failure To See Black Romantic Comedies.” She argues that ever since the romantic comedy’s resurgence in the 1990s, there’s essentially been a parallel black rom-com industry running alongside it, one that’s enjoyed frequent financial and critical success yet is still perceived as being separate from the traditional rom-com genre. The black rom-com boom kicked off in earnest with Eddie Murphy’s $131 million-grosser Boomerang. The 1992 hit was followed by films like Love Jones in 1997, How Stella Got Her Groove Back in 1998, and eventually The Best Man in 1999. The Best Man in particular established a template (and a casting pool) that rom-coms with all-black casts would use for the next two decades—right up through its hit 2013 sequel, The Best Man Holiday, a film that reignited conversations about how rom-coms with all-black casts are categorized.

The original Best Man has a simple yet effective premise: A group of close-knit college friends, now in their late 20s, reunite for a wedding. That alone would be enough to stir up old feelings, but complicating things even further is the fact that best man Harper Stewart (Diggs) has just written a buzzy debut novel that thinly fictionalizes their college experience. Long buried secrets and unresolved issues come to the surface, as Harper tries to figure out whether he wants to continue pursuing things with his free-spirited girlfriend, Robyn (Lathan), or revisit the might-have-been that he and career-driven college bestie Jordan Armstrong (Nia Long) never fully explored during their undergrad years.

Yet romance is just one aspect of a film that’s equally, if not more, interested in male friendship and friend group dynamics. The groom is rising NFL star Lance Sullivan (Morris Chestnut), a devout Christian and reformed playboy who’s about to marry long-time girlfriend and self-proclaimed “good girl” Mia Morgan (Monica Calhoun). Less reformed is Quentin Spivey (Terrence Howard), who’s more interested in wooing women with his Spanish guitar skills than finding any kind of direction in life. Rounding out Lance’s groomsmen is Julian “Murch” Murchison (Harold Perrineau), a soft-spoken intellectual who works with underprivileged inner city kids, even as his domineering girlfriend, Shelby (Melissa De Sousa), keeps pushing him to take a more prestigious gig as a lawyer. He eventually finds an unexpected spark with Candace “Candy” Sparks (Regina Hall, in her first film role), a stripper who’s hired to work Lance’s bachelor party.

In his debut feature, writer-director Malcolm D. Lee is observational rather than didactic. As in ’90s sitcoms like Seinfeld, Friends, and Living Single, part of the fun of The Best Man is watching a diverse group of personalities bounce off one another. And Lee isn’t afraid to let a lot of different world views co-exist. Jordan is an independent career woman who’s not necessarily looking for a committed relationship. Mia is a traditionalist who wants to dedicate herself to being a full-time wife and mother. Neither is framed as being in the wrong, and they’re still best friends. In fact, Lee has a keen sense for writing female characters who are intelligent, direct, and unapologetic about owning their sexualities, each in their own way.

“The movie really came out of my lack of seeing multi-dimensional black characters on screen, people I could really relate to on screen,” Lee explained in a 1999 CNN interview. Lee’s cousin, Spike Lee, loved the script and decided to produce the film. A benefit of The Best Man’s ensemble structure—which Lee cited as being influenced by the 1983 college reunion film The Big Chill—is that because we’re not rooting for just one central pair of characters, it’s less of a risk to make some of the characters flawed or even off-putting. Lance, in particular, engages in a fair bit of sexist hypocrisy that the film calls out but doesn’t necessarily try to resolve in an easy, simplistic way.

Fittingly, for a film about a novelist who turns his own life into fiction, The Best Man is interested in the line between reality and fantasy, in how our romantic projections can stop us from appreciating the strength of what we have in a real-world partnership. It’s about letting go of youthful dreams in order to forge new, more realistic ones. Because of the subtle way it delivers exposition and backstory, The Best Man is a rare rom-com that really rewards multiple viewings, not just as comfort food but to truly appreciate the intricate emotional dynamics.

The Best Man doesn’t reinvent the rom-com wheel, but Lee does a particularly nice job of anchoring familiar tropes in believable humanity. That’s most readily apparent in Howard’s unexpectedly grounded portrayal of Quentin, a character who could easily descend into a one-note playboy stereotype. Instead, Howard emphasizes Quentin’s humanity, intelligence, and slinkily provocative nature. He underplays the role in a way that makes Quentin genuinely magnetic, even as he’s frequently there for comedic relief. (Unfortunately, Howard is also one of many rom-com actors faced with real-life accusations of domestic assault, which makes it difficult to now simply sit back and enjoy his performance.)

Lee, who would later demonstrate a similar talent for working with ensembles in his 2017 smash hit Girls Trip, ensures the cast of The Best Man share a lived-in camaraderie that really makes them feel like a believable group of friends. They rib and support each other in equal measure. Freed from the uneven Jamaican accent that hindered him in his breakout performance in How Stella Got Her Groove Back, Diggs gets to put his charisma to much better use in his first true leading-man role. He’s got incredible chemistry with each of his co-stars, but the most important relationship in the film is the brotherhood between Lance and Harper, which is also the one most rocked by the revelations in Harper’s novel.

The Best Man certainly wasn’t the first black romance to focus on friendship as much as love. Forest Whitaker had explored that idea in his seminal 1995 romantic drama Waiting To Exhale, which is about a group of black women who rely on each other throughout their relationship ups and downs. And The Best Man was released the same year as Rick Famuyiwa’s curiously similar debut feature The Wood, which is about a group of lifelong friends from Inglewood who come together for a wedding. (There Diggs plays the groom instead of the best man.) But The Best Man solidified an ensemble-centric trend that would influence the genre for years to come. As Hunter Harris wrote in a 2017 Vulture essay: “[S]ometimes it feels like every modern black rom-com is nostalgic for The Best Man.”

Black rom-coms continued to find success in the early 2000s, but the late 2000s/early 2010s were just as artistically rough for romantic comedies with predominately black casts as they were for ones with predominately white ones. There were some exceptions, like Top Five, About Last Night, and Beyond The Lights, but otherwise the era was frequently an exercise in watching hugely talented actors like Taraji P. Henson, Gabrielle Union, Meagan Good, Michael Ealy, and Tasha Smith do their best with shoddy ensemble storytelling in films like Think Like A Man, Why Did I Get Married?, Jumping The Broom, and Baggage Claim.

So The Best Man’s 14-years-later sequel was a much-needed high point when it premiered in 2013. Rom-com sequels can be a mixed bag, but the nostalgia-tinged focus of The Best Man gracefully extends into a Christmas-themed reunion flick, one that explores how the events of the original film subtly rippled throughout its characters lives. Returning to writing and directing duties, Lee leaned harder into both comedy and melodrama, while still crafting an emotionally grounded film. The sequel even adds some appreciable depth to Shelby, the original’s worst-served character.

The Best Man Holiday exceeded box office expectations, eventually earning $70.5 million domestically on a $17 million budget. (The original had earned $34.1 million domestically on a $9 million budget.) The sequel also revealed some hypocrisies in the way the media discusses films with all-black casts. In a couple high-profile gaffes, The Best Man Holiday was referred to as “race-themed” or “urban,” despite the fact that it takes place in a high-end suburb with a cast that is all predominately one race—which also describes virtually every Nancy Meyers rom-com ever made. Lee was quick to push back on how the film was categorized. In a 2018 interview with The Root, he noted: “There’s gotta be different language around describing movies. If it’s a romantic comedy that’s got all black people in it, [it’s] still a romantic comedy.”

The groundbreaking success of Crazy Rich Asians and Black Panther (not to mention Girls Trip) may have finally started to shift that thinking a bit. Rather than target those movies at segmented audiences, there was a real push to embrace the universality of culturally specific stories. It’s yet to be seen how that shift will impact black rom-coms, however. After all, Crazy Rich Asians was to some extent paving new ground as a type of Asian-centric romantic comedy that hadn’t really existed before (at least not in American cinema). Romantic comedies with all-black casts have already been around for decades, so the shift will have to be in finally getting wider audiences to embrace them, something the box office success of Think Like A Man and The Best Man Holiday may have already started to pave the way for.

Although the Best Man’s promised third installment unfortunately seems to be indefinitely delayed, the first two films are worthy entries to the rom-com canons of their respective eras. The original, in particular, pulls off an impressive balancing act of tones, characters, and storylines. For many people, The Best Man has long been a beloved rom-com staple, one that’s even influenced real-life wedding traditions. But for those who may have mistakenly got the sense that The Best Man or other black rom-coms like it aren’t “for” them, it’s a great place to start delving into a brand-new corner of the rom-com canon. Take a glance at the filmographies of its talented stars, and you’ll have an even wider world of romances to discover.

Next time: In 1987, Cher and Nicolas Cage had us all Moonstruck.

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About the author

Caroline Siede

Contributor, The A.V. Club. Caroline Siede is a pop culture critic in Chicago, where the cold never bothers her anyway. Her interests include superhero movies, feminist theory, and Jane Austen novels.