In 1991, he had his first major film role, as boyfriend Tony Boer in "All I Want for Christmas". Other films in which he has since appeared include "Happy Gilmore", "The Wedding Singer", "Anger Management", "Little Nicky", "Just Go with It", "Daddy Day Care", "Good Boy!", and "Aliens in the Attic" (2009). He has a part in many of Adam Sandler's Happy Madison films, including "Grandma's Boy" (2006), "You Don't Mess with the Zohan" (2008), and "Father of the Year" (2018), and made a cameo appearance in the 2008 film "Get Smart".