The Best Man & 9 Other Great Black Romantic Comedies Of The 1990s & 2000s

The ’90s and 2000s saw an explosion of black actors in television and Hollywood, the likes of which had never been seen before in American screen history. A distinct genre on its own, black romantic comedies became the flavor of the millennium. In the early 1990s, movies like Malcolm X, Passenger 57, and Blade shot black actors into fame. On television, Martin, In Living Color and Living Single enraptured audiences to the screen.

moreover, black culture was going through a renaissance, propelled by the blaxploitation films of the 1970s and the emergence of rap as a cultural force in the 1980s and 1990s. Originally, black political revolt during the 1960s and 1970s took to the streets, and found its representation in media at the same time, with films such as Sweet Sweetback’s Baadasssss Song.  By the 1990s and 2000s, the black cultural revolution moved from the streets to the mediatic sphere, with Black America craving to see everyday stories of black people on the screen. Thus, the black romantic comedy genre was born.

10 The Best Man (1999)

90s heartthrobs, Terrence Howard, Taye Diggs, and Morris Chestnut, starred in The Best Man alongside Nia Long, Regina Hall, and Sanaa Lathan. Produced by Spike Lee, the film recycles the classic best friends romcom plot. Close friends from the past meet together again for a wedding, but old secrets come to light, threatening to ruin the upcoming marriage.

In this case, the groom’s best friend has a one night stand with the bride, threatening his friendships and his relationship. The plot is undeniably a product of the ’90s, as the groom was unfaithful countless times, but could not handle the bride’s one moment of infidelity.

9 How Stella Got Her Groove Back (1998)

How Stella Got Her Groove Back is a classic starring Angela Bassett, about a forty-year-old woman who meets and falls in love with a twenty-year-old man in Jamaica. The movie is an adaptation of a best-selling novel of the same name, written by Terry McMillan. In the book, based on real events in McMillan’s life, the author really does fall in love with, and marries, twenty-year-old Winston (Taye Diggs).

The plot is a simple story about a middle-aged woman who learns to fall in love once more after being self-sufficient for a long time. It stars supporting cast, Whoopi Goldberg and Regina King. McMillan also wrote Waiting To Exhale. In 1995, it was adapted into the popular rom-com by the same name, starring Whitney Houston and Angela Bassett.

8 Last Holiday (2006)

Last Holiday stars Queen Latifah as Georgie Byrd, an average department store worker who learns that she has only a few weeks to live, because of a rare brain condition. The timid woman with a bland life spends all her money on one last extravagant holiday in Europe. Georgia is also in love with Sean, her co-worker.

Unbeknownst to her, George shares her feelings. When she leaves suddenly for the Czech Republic, Sean sets out to find her. He finds her at The Grandhotel Pupp and rushes there to confess his feelings for her. Unfortunately, the film made less worldwide than it cost to produce.

7 Just Wright (2010)

Ever since her Living Single days, Queen Latifah has been coupled with leading black figures in film and sports. She dated men like Morris Chestnut and Grant Hill and even married Ll Cool J in Last Holiday. Last Holiday and Just Wright are the continuations of her niche as the romcom girl next door with whom audiences fall in love. Just Wright deserves an honorable mention because it came right at the end of the Golden Era of black romantic comedies.

Although films like Act Like A Lady, Think Like A Man would come out later (2012), audiences had grown tired of the conventional romantic comedy by the early 2010s. Films Like 500 Days Of Summer and Trainwreck would supersede the romantic comedy, adding a bitter reality to the sappy happiness and camaraderie of the 90s and 2000s.

6 I Think I Love My Wife (2007)

Chris Rock plays Richard Cooper, a husband in love with his wife, but in lust with an old friend in I Think I Love My Wife. Co-written by Chris Rock and Louis C.K., the movie features Gina Torres as his wife and Kerry Washington as his old friend, Nikki, trying to lure him into an affair.

The movie deals with the issue of infidelity in a marriage delicately, honestly portraying the issues that can lead a spouse to cheat on the other. I Think I Love My Wife is a simple feel-good film with no deep complexity or lesson. Cooper eventually realizes he loves his wife too much to cheat, so he rebuffs Nikki and returns home to his wife.

5 The Brothers (2001)

Like Taye Diggs, Morris Chestnut was the sweetheart of black romcoms of the ’90s and ’00s. A regular face in TV and film at the time, he stars in The Brothers with Shemar Moore, D. L. Hughley, and Gabrielle Union.

Similar to The Best Man, The Brothers follows four close friends dealing with their relationships – one of whom is about to get married. Unlike many black romcoms of the time, the movie also deals with issues of black identity in the US and how this affects romantic relationships among the cast.

4 A Thin Line Between Love And Hate (1996)

Playboy, Darnell Wright (Martin Lawrence) meets his match when Brandi Webb (Lynn Whitfield) steps into the Chocolate City club in Los Angeles. Darnell sets out to prove that he can seduce the hottest, richest woman in the neighborhood. After a series of romantic gestures aimed at winning her over, Brandi makes Darnell promise not to break her heart.

She confides in him that she has been heartbroken in the past and never wants to feel that way again. Darnell pretends to be in love with her so he can sleep with her, promising to never hurt her. This is only the beginning of Darnell’s troubles as Brandi begins to terrorize him as only a femme fatale can.

3 Two Can Play That Game (2001)

Two Can Play That Game is a star-studded romcom with Morris Chestnut, Vivica Fox, Gabrielle Union, and Mo’Nique. With a plot similar to Act Like A Lady, Think Like A Man, Shante Smith (Vivica Fox) must keep her man in check after he starts dating a new woman.

Shante believes that a man who threatens to cheat can be ‘trained’ and ‘manipulated’ into staying in love with his partner. Looked at through a feminist lens, the film does not age well. However, it is a funny film that exploits the male-female heterosexual dynamic, while celebrating female friendships.

2 Deliver Us From Eva (2001)

In the battle of the sexes, Ray (Ll Cool J) is hired to seduce the ice queen, Eva (Gabrielle Union). The film is a retelling of Shakespeare’s The Taming Of The Shrew in modern-day Los Angeles. Eva is too much of a match for master player, Ray and Ray turns down the pay after one date.

In typical rom-com fashion, they accidentally meet again immediately after the date and begin a real romance. Ray does manage to tame Eva after all. Drama ensues after Ray and Eva fall in love. Ray is the perfect man and makes all the other men around him look bad. Things soon escalate up until Ray ends up crashing his own funeral.

1 Love And Basketball (2000)

Cult class, Love and Basketball is the most recognized black rom-com of the era. Starring Omar Epps and Sanaa Lathan, the movie was also produced by Spike Lee and set in Los Angeles. Next-door neighbors, Quincy and Monica both share a love of basketball that eventually lead them to fall for each other.

Written by Gina Prince-Bythewood (The Secret Life Of Bees), Love And Basketball has a beautiful romantic storyline that follows two soulmates over the course of many years, and many career highs and lows. Like any good rom-com, the two lovers end up together, forever.