Paul Dinello moved to Chicago to study at DePaul University, where he got involved with the Second City comedy troupe and met fellow comedians Amy Sedaris and Stephen Colbert. The three of them moved to New York to create the sketch comedy show Exit 57, which originally aired on Comedy Central. After making his film debut in the Dolly Parton comedy feature Straight Talk, he appeared in the 1998 parody Plump Fiction, starring Tommy Davidson, Julie Brown, and Sandra Bernhard. He also appeared in the TV movie The Howard Beach Story. His stage credits include Jackie's Kosher Khristmas and Stitches (written by Amy and her brother David Sedaris). In 1999, Dinello re-teamed with the gang from Exit 57 to create Strangers With Candy, an after-school special parody of sorts on Comedy Central. In addition to writing and producing the series, he starred as art teacher Geoffrey Jellineck. The team also collaborated on a book called Wigfield: The Can-Do Town That Just May Not, published by Hyperion. Strangers With Candy was canceled in 2000, though Dinello began working on a movie version of the show in 2004.