Joseph O'Flaherty was born in Pittsburgh, Pennsylvania, but moved to Chicago, where he started his comedy career with the Second City Theater as Joe O'Flaherty. Along with several other Second City performers, he began appearing on the National Lampoon Radio Hour from 1973 to 1974. After seven years in Chicago, he moved to Toronto to help establish the Toronto Second City theatre troupe. During those years, he was one of the original writer/performers on SCTV, where he spent eight years on the show, playing such characters as Big Jim McBob (of Farm Film Report fame), Count Floyd/Floyd Robertson, and station owner/manager Guy Caballero who goes around in a wheelchair only for respect.