Colbert originally studied to be an actor, but became interested in improvisational theatre when he met famed Second City director Del Close while attending Northwestern University. He first performed professionally as an understudy for Steve Carell at Second City Chicago; among his troupe mates were comedians Paul Dinello and Amy Sedaris, with whom he developed the sketch comedy series Exit 57.
Colbert also wrote and performed on the short-lived Dana Carvey Show before collaborating with Sedaris and Dinello again on the cult television series Strangers with Candy. He gained considerable attention for his role on the latter as closeted gay history teacher Chuck Noblet. His work as a correspondent on Comedy Central's news-parody series The Daily Show first introduced him to a wide audience.
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