His television roles have included Ryan Nichols in ABC's V, Ike Prentiss in Showtime's Nurse Jackie, the lead role of Beaumont Darius Rosewood, Jr. in Fox's Rosewood, Hakeem Rashad in Prime Video's Goliath, and Barrett Cain in Fox's The Resident.

[1] Chestnut has been nominated for six NAACP Image Awards, winning for Nurse Jackie and The Best Man: The Final Chapters.

[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.

[9] In 1999, Chestnut starred in The Best Man with Taye Diggs and Nia Long, as Lance Sullivan, a professional football player on the eve of his wedding.

Chestnut starred in The Brothers (2001), a film centering on the themes of fidelity and success among young Black professionals.

Fox, in the romantic comedy Two Can Play That Game[13] and appeared as basketball player Tracey Reynolds in 2002 film Like Mike.

[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.

[23] In 2022, he once again played Lance Sullivan in the Peacock limited series The Best Man: The Final Chapters, winning his second NAACP Image Award.

[30] To prepare to reprise his role as professional football player Lance Sullivan in the movie The Best Man Holiday, Chestnut had to get into shape.

[33] In 2024, Chestnut reunited with The Best Man director Malcolm D. Lee, and co-stars Harold Perrineau and Taye Diggs, to found Sable Bourbon, a spirits brand.