The film stars an ensemble cast led by Taye Diggs and Nia Long, with the debut of Regina Hall.

In Chicago, Harper Stewart is an up-and-coming author whose debut novel, Unfinished Business, has been selected by Oprah's Book Club.

None of the friends approve of Murch's domineering girlfriend Shelby, and Harper chastises Quentin Spivey for being unable to settle down in a job.

The weekend reveals that Quentin has always been a free spirit, Lance has renounced his womanizing behavior, Harper is unsure about remaining a bachelor, and Murch has never been able to keep a secret.

Confronting Harper about their mutual attraction, Jordan admits she wants to have sex with him that night, before Robyn arrives for the wedding the next day, and they share a kiss.

As the groomsmen depart for the bachelor party, Jordan invites Harper to meet her later, and Murch finally stands up to Shelby.

As the party gets increasingly drunk, Murch falls for one of the strippers, Candy, and Harper calls Jordan, accepting her invitation.

[4][5] Jason Clark of AllMovie stated Howard "commands the screen with such abandon that one secretly wishes the film could have been all about his oddly captivating character".

[2] Rotten Tomatoes gives the film a 72% positive rating based on reviews by 71 critics, with the site's consensus stating "With a strong cast and a host of well-defined characters, The Best Man is an intelligent, funny romantic comedy that marks an impressive debut for writer/director Malcolm D.

All eight principal cast members received nominations at the 2000 NAACP Image Awards, with wins for Howard and Long, and for Outstanding Motion Picture.

Chestnut, Diggs, Hall, Howard, Lathan, Long, Perrineau, Calhoun and De Sousa returned from the first film.