Charles "Chip" Esten made his theatrical debut in London in 1991 when he portrayed Buddy Holly in the hit West End musical Buddy. It was during this run that he first appeared on the original British version of Whose Line is it Anyway? Later, while touring with Buddy in the United States, he was nominated for a Helen Hayes Award. He has also appeared as a different Buddy in the original cast of The Last Session.

Besides the American version of Whose Line Is It Anyway?, Esten's many television acting credits include The Brian Benben Show, The Crew, and the movies 61* and The Sleepwalker Killing. He's made guest appearances on such shows as Cheers, Murphy Brown, Married With Children, Just Shoot Me, JAG, Diagnosis Murder, Providence, Party of Five, and Star Trek: The Next Generation and Voyager. His feature film debut was in the Kevin Costner-directed The Postman. He has also appeared in Thirteen Days, Late Last Night, Save It For Later, and the Wim Wenders-directed Ten Minutes Older.