O'Donnell attended high school at The Bromfield School, which has a notable drama department, and he was involved in numerous productions both on the festival circuit and in community theater.
The film went on to become the highest grossing R-Rated comedy of all time.
In early 2001, he moved to Los Angeles to pursue work in film and television.
In the fall of 2001 he was cast as a lead in the US premiere of The Man Who Never Yet Saw Woman's Nakedness by Moritz Rinke, at The Odyssey Theatre in West Los Angeles.
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Not long after Crashers, Vince Vaughn invited O'Donnell to join him on the road for his Wild West Comedy Tour, a tour that hit 30 cities in 30 days across the country.