Early career Despite his parents' objections, he was able to support himself doing
stand-up routines at clubs near his home in Vancouver. He frequently performed at
strip clubs early in his career. He helped Rich Elwood start Punchlines Comedy Club. During this time, he was the head writer of
The Don Harron Show on
CTV and the host of
Comedy College on
CBC. Stiles was a regular improv performer with the Vancouver Theatresports League and Punchlines' "No Name Player" before joining
The Second City comedy ensemble at
Expo 86. He continued performing with Second City in
Toronto and later in
Los Angeles.
Whose Line Is It Anyway? and The Drew Carey Show By 1989, Stiles had gained the attention of the producers of the British improvisational comedy show
Whose Line Is It Anyway? Stiles was a regular on the show until its end in 1998. His performance on the program earned him both critical praise and a devoted fan following in the UK. In 1995, Stiles was asked by American comic
Drew Carey to be a regular on his sitcom
The Drew Carey Show. Stiles played Carey's erudite but underachieving best friend, Lewis Kiniski. In 1998, Carey successfully lobbied ABC to produce an
American version of Whose Line Is It Anyway? Following the final season of the British version in 1998, the American version premiered, with both Stiles and Carey credited as executive producers. Stiles received a nomination for the
Primetime Emmy Award for Outstanding Individual Performance in a Variety or Music Program in 2002 for his work on the show. A running gag of the show is Stiles' flashy dress shoes as well as his frequent impressions of American actress
Carol Channing. Though he never appeared in the series, Stiles (along with
Kaitlin Olson) performed in the taping of the unaired pilot episode of ''
Drew Carey's Green Screen Show, which involved improv games similar to Whose Line'' games played in front of a massive
green screen. Animation was later added to the improv footage. Stiles returned as performer and executive producer for
The CW's revival of
Whose Line Is It Anyway? in the summer of 2013.
Other television and film work Stiles appeared in the 1991 film
Hot Shots! as Mailman Farnham and its 1993 sequel,
Hot Shots! Part Deux, as marine Rabinowitz. He portrayed recurring character Dr. Herb Melnick on
Two and a Half Men from 2004 until the show's end in 2015. He made short guest appearances on ''
Parker Lewis Can't Lose, Murphy Brown, Mad About You, Mad TV, and Dharma & Greg. In July 2008, he was a guest star on Reno 911!'' as Sergeant Clift, an acting coach. During the
1994 Major League Baseball strike, Stiles appeared in several commercials for
Nike, spending time in an empty ballpark, doing things such as playing the organ and attempting to do
the wave alone. The commercials ended with the line: "Play ball. Please." In 2005, Stiles appeared in the
mockumentary Conker: Celebrity Squirrel produced for the promotion of the
Xbox video game
Conker: Live & Reloaded. This role led to gamers voting to induct him into the 2015 class of the DK Vine Hall of Fame. He appears as Bill, the soon to be ex-husband of Leanne, on the
Netflix comedy
Leanne, which debuted in July 2025. == Philanthropy ==