His first on-screen appearance was on King of Queens as Kirby Palmer in 1999. He appeared as "Mack Jr." in Johnson Family Vacation. Other film appearances include The Animal and Little Nicky.
On television, Bolden has guest starred on According to Jim, CSI: Miami, Malcolm in the Middle and has had recurring roles on both My Wife and Kids and The King of Queens. He also appeared in the telefilm Play'd: A Hip Hop Story. In 2001, he had a leading role in Macy Gray's music video "Sweet Baby". In 1999, he appeared in a commercial for McDonald's along with NBA's Kobe Bryant.[citation needed] Bolden took a decade-long hiatus from his acting after appearing in Fly Me to the Moon in 2008. But he has returned to acting, recently being cast as a main cast member in the 2021 AMC show, Millennials as Travis Lewis.

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