Ryan Stiles, the youngest of five children was born in Seattle, Washington to Canadian parents. He grew up in a modest but loving environment provided by his mother, a homemaker, and his father, a supervisor at a Vancouver-based processing plant. When he was 10, his family moved to Vancouver. Although he was a good student, Stiles admits that "being a high-school senior gave me too much freedom." He got so carried away with his flexible schedule that he quit school a few months shy of graduation. At age 17, he dropped out of high school to pursue comedy full-time. In spite of his parents' objections, he was able to support himself doing stand-u proutines at small comedy clubs near his home in Vancouver, British Columbia and co-founding the Punchlines comedy club with Rich Elwood. During this time he was the head writer of The Don Harron Show on CTV and the host of Comedy College on CBC. Ryan was a regular improv performer with the Vancouver Theatresports League and Punchline's No Name Player before joining Second City comedy ensemble at Expo 86. He continued with the Second City in Toronto, and later in L.A. Then in 1990 he landed a spot in the original British version of Whose Line Is It Anyway?, which lasted for 9 years. His performance on the program earned him both critical praise and a devoted fan following in the U.K. This break lead to numerous guest shots on U.S. TV programs such as Murphy Brown,Mad About You, and The John Larroquette Show, and an audition for the part as Lewis Kiniski on The Drew Carey Show. Work in the U.S. film industry soon followed, including roles in such feature films as Hot Shots!, Hot Shots! Part Deux, Courting Courtney, as well as the Academy Award-nominated short, Rainbow War.
In 1981, Stiles met Patricia McDonald at Punchlines where she was waitressing. They lived together for seven years before marrying in 1988. They have three children: Sam, Mackenzie, and Claire. When not working in Hollywood, he lives at his home on Lake Samish, outside Bellingham, Washington,where he has opened the Upfront Theatre, a small theatre dedicated to live improv comedy.
Stiles once lived in a house previously owned by Liberace in Sherman Oaks, California, but he sold it.
Stiles appeared in the 1991 film Hot Shots! as Dominic "Mailman" Farnum; Charlie Sheen and Jon Cryer also appear in the same movie as LT Sean "Topper" Harley and LT Jim "Wash Out" Pfaffenbach, respectively. He had another role in the 1993 sequel Hot Shots! Part Deux, as marine Rabinowitz. However, Jon Cryer didn't appeared in this move, Just Sheen