In the late 1960s Jack was working as a roofer in Chicago but got his acting start in such Chicago City Players productions as "Waiting for Godot", "The Death and Life of Sneaky Fitch", "The Successful Life of Three" and several plays by
Leonard Melfi and others--all directed by June Pyskacek--before becoming a a mainstay member of Pyskacek's Kingston Mines Theatre Company, where most notably he played Ranchman in the Midwest premiere of
Megan Terry's "The People Vs. Ranchman."