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Chestnut's first professional acting role was as "Jason" in Freddy's Nightmares: A Nightmare on Elm Street: The Series in the episode "A Family Affair" (season 2, episode 19) which aired on February 18, 1990. His first feature film role was as "Ricky Baker" in Boyz N the Hood (1991). He followed that up with roles in various TV movies. Chestnut also played a role on Patti LaBelle's short-lived sitcom Out All Night. His career continued to rise steadily with co-starring roles in standard big-budget studio films like Under Siege 2 (1995) and G.I. Jane (1997). As the decade ended, movies about young, professional African-Americans and their problems with family and relationships began to fill the cineplexes creating roles for Chestnut and many other talented black actors who had been stuck in minor television and film roles.
In 1998 he won the annual Madden Bowl. In 1999 Chestnut starred in The Best Man with Taye Diggs and Nia Long in which he played a professional football player on the eve of his wedding. 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. He subsequently starred in The Brothers, another film centering on the themes of fidelity and success among urban professionals.
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