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In 1999, the presence of black creatives on the big screen and behind the lens was in full bloom. Coming at the tail-end of a decade that introduced various films that helped shape the black consciousness and share our stories with the greater public, the year was considered a victory lap for actors, directors and audiences. One movie that arrived during this period was The Best Man, which added to the canon of pivotal films that spoke to urban America and captured the essence of the black community.

Written and directed by Malcolm D. Lee and produced by Spike Lee’s 40 Acres and a Mule Filmworks, The Best Man was released on October 22, 1999. Set primarily in New York City, the plot revolves around Harper (Taye Diggs), a rising author on the brink of releasing a book — that would turn him into a household name — who travels to the city to be the best man in his best friend Lance’s — who’s in the NFL — wedding. However, once a secret embedded between the lines of Harper’s book gets out, relationships are placed in jeopardy.

Boasting a star-studded cast also including Nia Long, Morris Chestnut, Harold Perrineau, Terrence Howard, Sanaa Lathan, Monica Calhoun, Melissa De Sousa and a pre-fame Regina Hall, The Best Man was a runaway hit, grossing $34 million on a $9 million dollar budget and was dubbed an instant classic. Critically acclaimed, the film, which won the award for Outstanding Motion Picture at the 2000 NAACP Image Awards, and earned all eight of the principal cast members nominations, as well, with Howard (Outstanding Supporting Actor in a Motion Picture) and Long (Outstanding Actress in a Motion Picture) both taking home hardware for their performances. Twenty years later, the movie remains one of the most beloved black films in modern history and continues to resonate with viewers, old and young.

In celebration of the 20th anniversary of this classic hitting theaters, REVOLT TV looks back at seven memorable moments from The Best Man that made it must-see cinema.

1. The Late-Night Jam Session

Emotions run high when Harper and Jordan reconnect, which conjures up memories of their potential romance that never happened. Harper, who reveals a passionate encounter between himself and Jordan to Murch, gives a play-by-play of what occurs when lust, fatigue and a little bit of Stevie Wonder are in the air.

2. The Poker Game

One of the first bonding exercises upon Lance’s groomsmen’s arrival in NYC is a friendly game of poker, during which he and the fellas reminisce on good times and become engrossed in a discussion about monogamy. However, when Quentin makes the suggestion that Lance’s fiancée may have been sexually involved with another man, things go awry, accounting for an intense moment that left viewers’ eyes glued to the screen.

3. The Bachelor Party

Any film about marriage without a bachelor party scene is simply incomplete and The Best Man doesn’t disappoint, as Lance’s crew of brethren put together the ultimate soiree for the groom-to-be. While Lance is subjected to the seduction of the adult entertainers, it is Murch who is ultimately the biggest winner of the night, as he receives the ride of his life.

4. The Fight

The climax of The Best Man occurs during the bachelor party, when a turned-up Harper loses possession of a valuable piece of information, which falls into the hands of the man of the hour. All hell breaks loose, hands are thrown, chaos ensues and strong bonds are on the verge of being broken.

5. The Argument

Jordan’s carnal desires are at their peak when the heated exchange between her, and a battered and bruised Harper occurs following his fight with Lance. As tempers flare, a sexually frustrated Jordan delivers the slap heard around the world before exiting stage left, leaving Harper with nothing left to do but curl up in the fetal position.

6. The Breakup

The toxic dynamic between Murch and girlfriend Shelby, who continuously exerts her control in the relationship, makes for one of the more intriguing subplots in the film. However, when Murch develops the will to walk away from Shelby and her demanding ways, his liberation is palpable and serves as a moment of triumph.

7. The Reception

Wedding bouquets are the apple of every single woman’s eye, as is the case for Shelby, who goes out of her way to increase her chances of finding undying love. However, she gets a bit more than she bargained for as she finally meets her match, who increases the temperature until it becomes to hot for the notorious man-eater to handle.