Is an excellent Texas Hold 'Em poker player. Recently (2005), held his own against 6 established poker professionals in a made for TV tournament.

Winner of the 1998 Madden Bowl, beating other celebrity talent as well as NFL stars in a tournament of John Madden Football.

Has worked with Steven Seagal twice. He was both Seagal's character's partner and main enemy. In Under Siege 2: Dark Territory (1995), Chestnut is Seagal's character's reluctant partner. In Half Past Dead (2002), he co-starred as the main villain.

Purchased $1.5 million estate in suburban Los Angeles.

Is a member of Phi Beta Sigma Fraternity, Incorporated.

Had a cameo appearance, but was uncredited, in the movie Higher Learning (1995) as one of the track runners on the team.