He began his career working as a stand-up comic in the Borscht Belt resorts of the Catskill Mountains northwest of New York City. His act grew in notoriety as he became a mainstay on late-night talk shows throughout the 1960s and 1970s, eventually developing into a headlining act on the Las Vegas casino circuit. He appeared in a few bit parts in films such as The Projectionist throughout the 1970s, but his breakout film role came in 1980 as a boorish nouveau riche golfer in the ensemble comedy Caddyshack, which was followed by two more successful films in which he starred: 1983's Easy Money and 1986's Back to School. Additional film work kept him busy through the rest of his life, mostly in comedies, but with a rare dramatic role in 1994's Natural Born Killers as an abusive father. Health troubles curtailed his output through the early 2000s before his death in 2004, following a month in a coma due to complications from heart valve surgery.