Ryan Lee Stiles was born on April 22, 1959 in Seattle, Washington. Later his family moved to Richmond, near Vancouver in British Colombia. He went to high school at Richmond Secondary School. He was a good student, but as he said "being a high-school senior gave me too much freedom" and he quit high school just a few months away from graduation. He was able to support himself for several years doing standup comedy.

In 1986 he joined Second City Comedy Ensemble in Toronto. In 1990 he was invited to join the Second City group in Los Angeles. He had movie parts in "Hot Shots" and "Hot Shots Part Deux" His mother hung his publicity photo from the movie, which he was in an Air Force uniform for, right next the pictures of his three brothers who were all in the real Air Force.

He met his wife Pat McDonald in the 1970’s and they married in 1989. Together they had a daughter, Mackenzie and a son, Sam. He met his friend and partner in crime, Colin Mochrie, in 1985 when they were both supporting characters on a Canadian short film called "Rainbow War"

He has done the UK version of Whose Line is it Anyway? from 1989 to 1998. He didn’t enjoy that much, because of his fear of flying (he confessed in an interview that he once had to have a stewardess hold his hand during turbulence) He also helped convince ABC to create the U.S. version of Wliia as a summer replacement. He both produces and stars in the U.S. version, also know as Drew’s Line.

Besides being in Wliia Ryan also stars in the Drew Carey show as Drew’s best friend Lewis. He has guest-stared in several shows. He now lives with his family in a suburb of Los Angeles