He developed his comedic talent while attending New York University. Before breaking through in Hollywood, he worked as a comedian and appeared as a regular cast member on Saturday Night Live.
In 1999, he founded a production company called Happy Madison, a title he created from combining the names of two of his films, Happy Gilmore and Billy Madison.
His mother Judy was a nursery school teacher and his father Stanley was an electrical engineer. He married actress Jacqueline Samantha Titone in June 2003, and the couple had two daughters together. His daughters' names are Sadie and Sunny Sandler.