Stiles had first met Colin Mochrie years before while performing stand-up. They first performed together in Vancouver TheaterSports then in Second City, Toronto.There were a number of games which paired Mochrie and Stiles at every playing. Though other performers did so, he was the most common performer to make bald jokes at Mochrie. In return, Mochrie often made jokes about Stiles's height, nose, attractiveness, and tendency to wear exotic, flamboyant shoes, which were designed by George Esquivel. However, he would sometimes stand up to or make jokes at the other performers (including Drew Carey) who made fun of Mochrie's baldness or Mochrie in general, mostly during Scenes From A Hat.