Boys n the Hood and breakout

Chestnut's first professional acting role was as Jason in Freddy's Nightmares – A Nightmare on Elm Street: The Series, season 2, episode 19 ("A Family Affair"), which aired on February 18, 1990. His first feature film role was as Ricky Baker in Boyz n the Hood (1991).^[7] He followed that up with roles in various TV movies, notably including the Peabody Award winning Disney Channel film The Ernest Green Story, in which he played Ernest Green. Chestnut also appeared in Patti LaBelle's short-lived sitcom Out All Night.^[8] His career continued to rise steadily with co-starring roles in standard big-budget studio films such as Under Siege 2: Dark Territory (1995) with Steven Seagal and Katherine Heigl, and G.I. Jane (1997) with Demi Moore. He was also a regular cast member on C-16, in the role of Special Agent Mal Robinson, from 1997 to 1998.^[9]

The Best Man and other films

In 1999, Chestnut starred in The Best Man with Taye Diggs and Nia Long, as a professional football player on the eve of his wedding.^[10] The Best Man earned positive reviews from the press and did well at the box office. For his performance, Chestnut earned an NAACP Image Award nomination.^[11] He again played a football player in Disney's The Game Plan (2007), co-starring opposite Dwayne Johnson.

Chestnut starred in The Brothers (2001), a film centering on the themes of fidelity and success among young Black professionals.^[12] That same year, he portrayed Keith Fenton, the love interest of Vivica A. Fox, in the romantic comedy Two Can Play That Game^[13] and appeared as basketball player Tracey Reynolds in 2002 film Like Mike.^[14] In 2004, he played firefighter Tommy Drake in Ladder 49, opposite John Travolta and Joaquin Phoenix.^[15]

He has worked with Steven Seagal three times: Under Siege 2: Dark Territory (1995) as his reluctant partner^[16] and lead male villain in Half Past Dead (2002)^[17] and Prince of Pistols (2008).

Chestnut appeared in four films in 2013: Identity Thief, The Call, Kick-Ass 2 (playing Omari Hardwick's character from the first film), and The Best Man sequel The Best Man Holiday, in which he reprised his role as Lance Sullivan, earning him another NAACP Image Award nomination.^[18]

Recent cinema work includes The Perfect Guy, Heist (both 2015) and When the Bough Breaks (2016)

Television work

In recent years, the majority of Chestnut's work has been in television.

From 2009 to 2011, Chestnut starred in the ABC science fiction drama V, based on the classic 1983 miniseries. In 2013, he joined the cast of Showtime's medical dramedy Nurse Jackie as war veteran Dr. Ike Prentiss, staying for two seasons.^[19] For his performance in the latter, he won the NAACP Image Award for Outstanding Supporting Actor in a Comedy Series.^[20] Shortly afterward, he co-starred in the TNT crime drama Legends opposite Sean Bean.

From 2015 to 2017, Chestnut played the lead role of pathologist Dr. Beaumont "Rosie" Rosewood Jr. in the Fox crime procedural Rosewood,^[21] receiving another NAACP image Award nomination as a result.^[22]

Chestnut had main roles in the second season of Prime Video's Goliath, and NBC's The Enemy Within. He played cold-hearted neurosurgeon Barrett Cain in seasons three and four of the Fox medical drama The Resident, and appeared as Raymond Dupont in the short-lived Our Kind of People, also for Fox.^[23]

In 2022, he once again played Lance Sullivan in the Peacock limited series The Best Man: The Final Chapters. As of 2023, he hosts the OWN docuseries Rebuilding Black Wall Street, produced by Sunwise Media.^[24] In 2024, he starred opposite Diarra Kilpatrick in the BET+ mystery-dramedy Diarra from Detroit.

In 2025, Chestnut will star in the CBS medical-mystery series Watson, playing Dr. Watson from the Sherlock Holmes stories.^[25]

Film

Television