The Best Man (1999)
The Best Man (1999) poster
Directed by Malcolm D. Lee
Produced by Spike Lee
Sam Kitt
Bill Carraro
Written by Malcolm D. Lee

Taye Diggs
Nia Long
Morris Chestnut
Harold Perrineau
Terrence Howard
Sanaa Lathan
Monica Calhoun
Melissa De Sousa

Music by Stanley Clarke
Cinematography Frank Prinzi
Editing by Cara Silverman
Distributed by Universal Pictures
Release October 22, 1999 (US)
Running time 120 minutes
Country United States
Language English
Budget $9,000,000
Gross revenue $34,102,780
Followed by The Best Man Holiday

The Best Man is an American 1999 romantic comedy-drama film, written and directed by Malcolm D. Lee. It was produced by 40 Acres and a Mule Filmworks, with Lee's cousin, Spike Lee, serving as producer. The film stars Taye Diggs, Nia Long, Morris Chestnut and Sanaa Lathan, and is considered to be a male-centered answer to female-targeted films such as Waiting to Exhale.

A Christmas-themed sequel, The Best Man Holiday, was released on November 15, 2013 with a reunited cast.


Harper Stewart (Diggs) is a young man living in Chicago who is about to hit the big time professionally. His debut novel, ominously titled Unfinished Business, has been selected by Oprah's Book Club. He has a beautiful and devoted girlfriend, Robin (Lathan), and his best friend Lance (Chestnut) is getting married on the weekend in New York. In an early scene with Harper and Robin lounging in a tub, it becomes clear that all is not well. Robin merely sighs contentedly and idly mentions that she could stay like this forever. For Harper, life is just beginning, and he feels that committing to a woman now that he is on the verge of success would be a death-knell for him.

To complicate matters further, Harper's new book, which is autobiographical, has fallen into the wrong hands. Jordan (Long), an old woulda-coulda-shoulda flame of Harper's, has read an advance copy that seems to be working its way through Harper's inner circle, coincidentally the other members of the wedding party. In the novel are several unsavory fictionalized characterizations of Harper's real-life friends during their college years. These friends all take it in good stride when they talk to Harper face-to-face, but their hurt causes at least one of them to want to teach Harper a lesson. Jordan learns that Harper's book is unabashedly flattering in its portrayal of a character based on her, however, and she decides to test the waters with Harper at this vulnerable stage. To make matters worse, while in college Harper had an affair with Mia, Lance's then-girlfriend and current bride-to-be. Lance does not know, and Harper is anxious to keep the secret.


  • Taye Diggs as Harper Stewart, the main protagonist and titular best man of Lance
  • Nia Long as Jordan Armstrong, a good friend of Harper's from college
  • Morris Chestnut as Lance Sullivan, Harper's best friend, a star professional running back, and the groom
  • Harold Perrineau as Julian Murch, another friend of Harper's and a groomsmen
  • Terrence Howard as Quentin Spivey, another friend of Harper's and a groomsmen. He serves as both the comic relief and a minor antagonist.
  • Sanaa Lathan as Robin, Harper's girlfriend
  • Melissa De Sousa as Shelby, Murch's snobbish, high maintenance girlfriend
  • Monica Calhoun as Mia Morgan, the bride, who had an affair with Harper
  • Regina Hall as Candace (aka Candy), a kind-hearted stripper with whom Murch falls in love upon meeting her
  • Jim Moody as Uncle Skeeter, Lance's silly uncle
  • Jarrod Bunch as Wayne
  • Victoria Dillard as Anita
The Best Man films

The Best ManThe Best Man Holiday