The Best Man Cast: Their Ages And Careers

The cast of the 1999 comedy-drama film The Best Man and its subsequent franchise instalments have become household names. The film's ensemble cast includes Taye Diggs, Nia Long, Morris Chestnut, Harold Perrineau, Terrence Howard, Sanaa Lathan, Melissa De Sousa, and Regina Hall, who made her on-screen debut with this film. The cast has gone on to achieve success in various film and television projects, with some becoming staples of Black culture. The franchise's latest instalment, The Best Man: The Final Chapters, premiered in 2022, bringing the story and its beloved characters to a close.

Taye Diggs' career after The Best Man

Scott Leo "Taye" Diggs, born on January 2, 1971, in Newark, New Jersey, has had a prolific career in film, television, and theatre since his role in The Best Man in 1999.

In 2002, Diggs reprised his role as The Bandleader in the film adaptation of the Broadway revival of Chicago, and also played opposite Christian Bale in the dystopian sci-fi thriller Equilibrium. In the same year, he appeared in the film Brown Sugar, which further established his career as a leading man in Black cinema.

Diggs continued to take on a variety of roles in the following years, including a major role in the live-action adaptation of the comic Dylan Dog: Dead of Night (2011), and a guest role on The West Wing as a Secret Service agent. He also returned to his stage roots, filling in as Billy Flynn on Broadway and appearing in the Broadway production of Hedwig and the Angry Inch in 2015.

From 2014 to 2016, Diggs starred in the TNT serial crime drama Murder in the First, which ran for three seasons. He also returned to the Best Man franchise, reprising his role in The Best Man Holiday in 2013 and The Best Man: The Final Chapters in 2022.

In addition to his acting career, Diggs has written four children's books and is the co-artistic director of a dance company, Dre.dance. He has also made appearances on reality competition shows such as Lip Sync Battle, where he is the only two-time winner.

Most recently, in 2023, Diggs co-starred in the Peacock streaming film The Comeback, and the BET+ films Love & Murder: Atlanta Playboy. He also starred and was an executive producer for Terry McMillan Presents: Forever, which premiered on Lifetime in 2024.

Nia Long's career before The Best Man

Nia Long, born on October 30, 1970, is an American actress known for her work in Black cinema. Before starring in The Best Man in 1999, Long had already built an impressive career in both film and television.

Long's first notable role was on the soap opera Guiding Light, where she portrayed Kathryn "Kat" Speakes from 1991 to 1994. However, her breakthrough role came in 1991 when she starred in John Singleton's classic film Boyz n the Hood. Long played the role of Brandi, and the film helped launch her career and build her confidence as an actress. She also worked with Singleton on the film Poetic Justice in 1993.

In addition to her film roles, Long found success on television. From 1991 to 1995, she played Will Smith's girlfriend and fiancée, Beulah "Lisa" Wilkes, on the NBC sitcom The Fresh Prince of Bel-Air. She also appeared as Claudia, another love interest of Smith's, in the second season of the show. Long's other television credits during this time include appearances on Living Single and The B.R.A.T. Patrol.

Long continued to build her film resume throughout the 1990s, appearing in movies such as Made in America (1993), Friday (1995), and Soul Food (1997). She also starred in the romantic cult classic Love Jones (1997) alongside Larenz Tate, portraying the character Nina Mosley. This role is particularly beloved by fans, who have longed for Long to reprise it.

In 1999, Long took on the role of Jordan Armstrong in The Best Man, an American comedy-drama film written and directed by Malcolm D. Lee. The film received positive reviews and was a groundbreaking moment in Black cinema, featuring an ensemble cast of actors who have since become household names. Long's performance in The Best Man earned her a Best Actress (Theatrical) award at the 2000 Black Reel Awards.

Regina Hall's career after The Best Man

Regina Hall's career took off after her role in The Best Man. The film marked her debut as an actress, and she has since become a household name in Hollywood.

Hall's portrayal of Candace "Candy" Sparks in The Best Man left a lasting impression on viewers. The role was small, but her charisma shone through, and she was soon offered a range of other film and television roles.

In the years following The Best Man, Hall appeared in several notable productions. She gained recognition for her role in the comedy-horror-spoof Scary Movie (2000) and its sequels, Scary Movie 2 (2001), Scary Movie 3 (2003), and Scary Movie 4 (2006). She also had a recurring role on the prime-time drama Ally McBeal in 2001-02 and starred in the action-drama Paid in Full (2002). Hall's versatility as an actress was further demonstrated in leading roles in films such as Malibu's Most Wanted, King's Ransom, and The Honeymooners.

In addition to her film career, Hall has also appeared on television. From its fall 2010 debut until a series overhaul in January 2011, she portrayed Deputy District Attorney Evelyn Price on Law & Order: LA. She has also had roles in other TV movies and series, including Disappearing Acts, Mardi Gras: Spring Break, and Second Generation Wayans.

Hall returned to the role of Candace "Candy" Sparks in the 2013 sequel The Best Man Holiday, reprising her character from the original film. She also appeared in the 2014 film About Last Night, co-starring Kevin Hart, and the 2015 film People Places Things, where she played the love interest of a newly divorced man.

In 2016, Hall starred in Barbershop: The Next Cut and Girls Trip (2017), which became a critical and commercial success. In 2018, she received critical acclaim for her performance in Support the Girls, becoming the first African American to win the New York Film Critics Circle Award for Best Actress. That same year, she was invited to join the Academy of Motion Picture Arts and Sciences.

Hall has continued to build an impressive résumé, starring in films such as Little (2019) and The Hate U Give (2018). She has also ventured into television, with roles in Black Monday (2019-21) and Nine Perfect Strangers (2021). In 2022, she hosted the Academy Awards and appeared in the horror film Master and the megachurch dramedy Honk for Jesus. Save Your Soul.

Terrence Howard's career before The Best Man

Terrence Howard, who played Quentin Spivey in The Best Man, had already been acting for several years before the film's release in 1999. He made his acting debut in 1992, portraying Jackie Jackson in the ABC miniseries The Jacksons: An American Dream. The following year, he appeared in the TV series Living Single and NYPD Blue. In 1995, he landed his big break in film, starring in Dead Presidents and Mr. Holland's Opus. He also appeared in the music video for Ashanti's 2002 single "Foolish".

Howard's career progressed with several notable TV appearances, including a lead role in the UPN TV series Sparks (1996) and a role in Soul Food (2000). He also played Cassius Clay in King of the World (2000) and Ralph Abernathy in Boycott (2001).

In 2004, Howard played the role of musician Ray Charles in Ray, a film that earned him significant critical acclaim. The following year, he portrayed a pimp and aspiring rapper in Hustle & Flow, a performance that earned him an Academy Award nomination for Best Actor.

In 2008, Howard played James "Rhodey" Rhodes in the Marvel film Iron Man. He was slated to reprise his role in the sequel as War Machine but was replaced by Don Cheadle after allegedly being asked to take a significant pay cut.

In addition to his acting career, Howard is also a self-taught musician, playing both the piano and the guitar. He has also worked as a film producer and hosted the PBS series Independent Lens in 2008.

Morris Chestnut's career after The Best Man

After his role in The Best Man, Morris Chestnut went on to star in several other films and TV shows. In 2001, he played Keith Fenton, a playboy attorney, in the romantic comedy Two Can Play That Game, alongside Vivica A. Fox and Gabrielle Union. Chestnut has worked with Union on three other occasions, including The Brothers (2001), a film exploring the themes of fidelity and success among young Black professionals.

Chestnut's other early 2000s roles include firefighter Tommy Drake in Ladder 49 (2004), opposite John Travolta and Joaquin Phoenix, and a cameo as a caddish ex-boyfriend in the Taraji P. Henson rom-com Think Like A Man (2012). Chestnut has also worked with Steven Seagal on three films: Under Siege 2: Dark Territory (1995), Half Past Dead (2002), and Prince of Pistols (2008).

In 2013, Chestnut reprised his role as Lance Sullivan in The Best Man Holiday, the sequel to The Best Man. That same year, he joined the cast of the Showtime medical dramedy Nurse Jackie, playing war veteran Dr. Ike Prentiss for two seasons. Chestnut won the NAACP Image Award for Outstanding Supporting Actor in a Comedy Series for this role.

Chestnut has since taken on several television roles, including starring as pathologist Dr. Beaumont "Rosie" Rosewood Jr. in the Fox crime procedural Rosewood (2015-2017), and as Hakeem Rashad in the second season of the Prime Video series Goliath. In 2022, Chestnut once again reprised his role as Lance Sullivan in the Peacock limited series The Best Man: The Final Chapters, winning his second NAACP Image Award for the role.

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