- 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.
- Is an excellent Texas Hold 'Em poker player. Recently (2005), held his own against six established poker professionals in a television tournament.
- Winner of the 1998 Madden Bowl, beating other celebrity talent as well as NFL stars in a tournament of John Madden Football.
- Had a cameo appearance, but was uncredited, in the movie Higher Learning (1995) as one of the track runners on the team.
- Has two children: Grant Chestnut and Paige Chestnut.
- He was awarded a Star on the Hollywood Walk of Fame at 6353 Hollywood Boulevard in Hollywood, California on March 23, 2022.
- Purchased $1.5 million estate in suburban Los Angeles.
- Despite the fact that his birthday is on New Year's Day, he does not celebrate his birthday.
- He has appeared in one film that has been selected for the National Film Registry by the Library of Congress as being "culturally, historically or aesthetically" significant: Boyz n the Hood (1991).
- A former bank teller.
- Born on the same date as Verne Troyer.
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