Ryan also starred in the comedy sitcom, "The Drew Carey Show " from 1995 to 2004 playing Drew's quick-witted friend, Lewis Kiniski. Ryan appeared in the Academy Award-nominated film, Rainbow War. The film was centered on the World’s Fair that occurred in 1986 in Vancouver. Both Ryan and Colin were cast in the film. During the Oscars, Rainbow War received an Oscar nomination for Best Short Film.

Ryan tours with Greg Proops, Chip Esten, and Jeff B. Davis with the “Whose Line Is It Anyway?” live show. He had a recurring role on a famous television sitcom called "Two and a Half Men". He filmed a pilot for a Canadian sitcom called "Memory Lanes" starring him and Sean Masterson.

Ryan has also been successful in starring in many commercials. In 1994, Nike opted to start baseball ads where they targeted ending the strike involving the MLB. For the ad campaign, Ryan starred in several ads where he tried various moves in an empty stadium by himself. Apart from Nike’s ads, Stile has been featured on many other commercials including ads for Zaxby’s, Kinko’s, Progressive Insurance, KFC, Pizza Hut and Playskool.