You've Most Likely Seen Him In ...
...the groundbreaking 1991 film Boyz N the Hood. While Cuba Gooding Jr. got the biggest career boost from the film, and Ice Cube laid the groundwork for a post-hip-hop career in the movies, it was Chestnut who played the pivotal character of Ricky, whose fate provides the movie's emotional climax.

Unless You've Really Been Paying Attention, in Which Case You Remember Him From ...
...early '90s television. Perhaps you were into NBC's streak of sitcoms starring African-American music stars? To go with Will Smith in The Fresh Prince of Bel Air and LL Cool J on In the House, we got one glorious season of Out All Night, where Chestnut co-owned a swanky nightclub with none other than Patti LaBelle.

"Wait, So He's That Guy From ..."
...A whole bunch of turn-of-the-century dramadies that explored the eternal interpersonal tug-of-war between African-American men and women, often co-starring Gabrielle Union. Before Tyler Perry went and made those movies silly. There was The Best Man in 1999, then The Brothers and Two Can Play That Game in 2001, and Breakin' All the Rules in 2004.

You Can Also Go Back and Spot Him In ...
...any number of action movies as a sidekick. He fought alongside Steven Seagal in Under Seige 2: Dark Territory. He fought alongside Demi Moore in G.I. Jane. He played football with The Rock in The Game Plan. He switched things up by fighting against Steven Seagal in Half-Past Dead. There's a sense of disappointment that Chestnut never graduated to an action blockbuster of his own. He sure cuts the right silhouette for it.

Perhaps Your Cultural Tastes Extend Beyond the Movies, In Which Case...
...Recent television appearances have brought Chestnut in front of quite a few eyeballs. He rode the rollercoaster of ABC's remake of the alien-invasion thriller V, and he spent a good bit of time poking around the haunted house during the first season of American Horror Story.

You Can Find Him Now In ...
..Brad Anderson's The Call, reuniting him with his The Last Boy Scout co-star Halle Berry. When he'll be reunited with Patti LaBelle, well, we can only wait and hope.
 

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Working Actor: Where You've Seen Josh Hamilton Before