In 1992, his potential was spotted by the makers of Whose Line Is It Anyway? who asked him to audition for an episode, which he did successfully. Consequently, Esten made his debut on the Channel 4 show and "won" the episode, reading the credits in the style of an auctioneer. He subsequently appeared in more episodes later the same year when the show did a run in New York . At the time, the show needed a second specialist improvisational singer to account for episodes when Mike McShane wasn't on, and thus Esten proved a worthwhile experiment.
Esten made one more appearance in the UK edition in 1994 before moving back to the USA and playing the role of Luke in Party of Five . Although in demand as a jobbing actor on stage and screen thereafter, it was his 1999 return to Whose Line Is It Anyway? — in the show's new-look American format, with Drew Carey as host — which established him with a mainstream American audience. He became a regular "fourth contestant" on the show and continues to be adept at the singing games in particular, though has satisfied his early potential to become an outstanding all-round improviser.
In 2001, Esten appeared in Billy Crystal's TV movie 61* as Kevin Maris, the son of legendary New York Yankees slugger Roger Maris. Esten had roles in two Kevin Costner movies, The Postman and Thirteen Days .
Esten also starred in a public service video, "Riding Straight", produced for the Motorcycle Safety Foundation's curriculum, "Motorcycle Rider Course: Riding and Street Skills" (MRC:RSS). Esten portrayed a surfer dude, a snuff-dipping hick, and a concerned friend in a bar. Esten's performance, in turns over-the-top comedy and sincere public service message, greatly invigorated the drug- and alcohol-awareness portion of the MRC:RSS. The video, part of a curriculum update for a younger "MTV generation" audience, replaced a filmstrip-like anti-alcohol short that was a more effective sedative (especially after a long weekend of rider training) than some of the drugs it warned about.
Esten appeared in several episodes of The Office as Josh Porter, the regional manager of Dunder Mifflin's Stamford branch. Chip's television guest star roles continue to increase with appearences on The New Adventures of Old Christine and several episodes of ER. He also appeared as Kelly Bundy's equally stupid ex-con boyfriend in the final episode of Married... with Children .
He portrayed a Klingon named Divok in the Star Trek: The Next Generation episode " Rightful Heir" as well as Dathan, an Enaran, in the Star Trek: Voyager episode "Remember."
Esten also had a recurring role on the TV show The Winner, playing the boyfriend of Alison. Chip appeared on the TV show Lois & Clark: The New Adventures of Superman in Season 4, Episode 10 "Stop The Presses" as Ethan Press as well as The
New Adventures of Old Christine and HBO's Big Love.
Look for Chip Esten in the new ABC series Nashville. Chip stars as Deacon Clayborne in this new highly-acclaimed television show which airs Wednesdays on ABC at 10 p.m.