The Best Man marked one of Taye Diggs' first big movie roles following his film debut in 1998's How Stella Got Her Groove Back with Angela Bassett. He later went on to reprise his Broadway role as Benny in the 2005 movie adaptation of Rent, and has starred in dozens of films and TV shows since, including All American, Set It Up, Private Practice, Day Break and Kevin Hill, to name a few.
Nia Long was a booked and busy actress before she starred as Jordan in The Best Man, having appeared on shows like Guiding Light and The Fresh Prince of Bel Air. In recent years, she's taken on roles in NCIS: Los Angeles and Empire, and starred in films such as Beaches, 47 Meters Down: Uncaged, Fatal Affair, and most recently, Netflix's Look Both Ways.
The Best Man marked Regina Hall's film debut, and she has certainly come a long way since. The actress cemented herself as one of Hollywood's funniest stars through her role as Brenda in the Scary Movie franchise and other comedies such as Think Like a Man, Girls Trip and Little.
In addition to serious roles in projects like The Hate You Give, Master and Nine Perfect Strangers, Regina most recently starred in the Netflix comedy Me Time with Kevin Hart and Mark Wahlberg.
Terrence Howard appeared in dozens of TV shows and movies prior to playing Quentin in The Best Man. But perhaps the actor's most notable role in recent years is as Lucious Lyon on the hit series Empire.
After The Best Man, Terrence went on to star in TV shows like Sparks, Street Time and Law & Order: LA, as well as films like Big Momma's House, The Salon, The Butler, Prisoners, Triumph, Iron Man and Hustle & Flow, for which he was nominated for an Oscar.
The Best Man: The Last Chapters is the latest among Morris Chestnut's long list of TV credits, having starred on shows such as Our Kind of People, The Resident, The Enemy Within, Rosewood, Nurse Jackie and more. He has even reunited with a few of his The Best Man co-stars on-screen, including Taye Diggs on the show All American and Regina Hall in the film Girls Trip.
Harold Perrineau has some of film and TV's most iconic titles on his resume, having appeared in projects like Romeo + Juliet, The Matrix films and the hit show Lost. Among his most recent credits includes the series From, Claws, The Rookie and Star, as well as the 2018 Netflix film Dumplin', which he starred in alongside Jennifer Aniston.
A year after playing Robyn in 1999's The Best Man, Sanaa Lathan went on to star in another beloved rom-com Love & Basketball with Gabrielle Union and The Best Man co-star Regina Hall. She also reunited with her on-screen husband Taye Diggs in the 2002 film Brown Sugar.
She went on to voice Donna Tubbs on the animated series The Cleveland Show and Family Guy, as well as appeared in movies and shows such as Succession, Nappily Ever After, Now You See Me 2 and Nip/Tuck, among many other credits.
Before The Best Man, Melissa De Sousa starred in the TV series Valley of the Dolls. And she has been in quite a few projects since. You may recognize her as Karen (a.k.a. Miss New York) from Miss Congeniality or Gabriella on the sitcom Reed Between the Lines with Tracee Ellis Ross. In recent years, she has made several TV appearances on shows like Black Lightning, Our Kind of People, On Becoming a God in Central Florida, Criminal Minds and more.