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After graduating from high school, Myers was accepted into the Second City Canadian touring company.

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In 1998, Myers played one of his rare non-comedic roles in the film 54: Steve Rubell, proprietor of New York City's famous Studio 54, a 1970s discotheque.

The film was moderately successful, and Myers's performance was widely praised.

The next year, he starred in the British children's TV program Wide Awake Club, parodying the show's normal exuberance with his own "Sound Asleep Club", in partnership with Neil Mullarkey.

He returned to Toronto and Second City in 1986 as a cast member in the Second City's Toronto main stage show, Second City Theatre.

Myers wrote another sketch, "Kurt and Dieter", co-starring with Second City's Dana Andersen and also directed by Novak, which would later turn into the popular "Sprockets" sketch on Saturday Night Live.