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Flynn was born on Chicago's south side and raised in Waukegan, Ill., the third of six children. Although he acted in plays during his school years, it wasn't until he was getting ready to graduate from Bradley University in Peoria, Ill., that he began to think that performing was something he could actually do for a living. After college, Flynn returned to Chicago and pursued live theater. He appeared at the Steppenwolf and Goodman theaters, and worked with Aidan Quinn (in Hamlet) and Brian Dennehey (in Galileo, at the Goodman), among others. Always seeking to expand his skills, he later became a mainstay at Chicago's ImprovOlympic, renowned for performing and teaching long-form improvisational theater, and went on to be a member of the Second City Comedy Troupe in Chicago.

A two-time Jefferson Award nominee, Flynn has also made many appearances in feature-films, including Magnolia (working with director Paul Thomas Anderson), Home Alone 3, The Fugitive, Chain Reaction, Rookie of the Year, Baby's Day Out and Major League. On television, Flynn has performed a variety of guest-starring roles on such series as C.S.I.: Crime Scene Investigation, Boston Public, NYPD Blue, Arliss, The Drew Carey Show, That ‘70s Show, Seinfeld, Ellen and Family Law.

Away from the set, Flynn can often be found honing his skills at the ImprovOlympic West in Hollywood, where he has appeared for three years in the popular show Beer, Shark, Mice. A sports fan, he plays on a local softball team, and also enjoys a weekly game of poker. He is single and lives in the Los Angeles area.