He worked as a stand-up comic in the twilight of the late-80's comedy boom, and achieved some notoriety for his acerbic take on American life. His comedy CD 'No Cure For Cancer' featured the hiot novelty song, 'I'm An A**hole.' He also appeared on the MTV game show 'Remote Control.'
Leary began appearing in movies, including 'The Ref,' 'Demolition Man,' and 'Two If By Sea.' He voiced a character in the successful animated film 'Ice Age,' and appeared as the lead in the FX fireman hit, 'Rescue Me,' for which he was nominated for a Golden Globe.