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Allen Covert

Allen Covert has built a career around comedy, often contributing far more to a movie than his time on screen might suggest. Born on October 13, 1964, in West Palm Beach, Covert is an actor and comedian whose work also extends into writing, screenwriting and producing. His first film role was as a cruise ship bartender in 1989’s Going Overboard, which also marked Adam Sandler’s first cinematic appearance. That small part began a long-running creative association. Covert went on to appear in several Sandler films, including a minor role as Otto, the homeless caddy, in Happy Gilmore. His first prominent part came in 1998’s The Wedding Singer, alongside Sandler and Drew Barrymore. Covert continued appearing in Sandler’s next four films, gaining 40 pounds for his role in Little Nicky. From 50 First Dates onward, his appearances generally shifted back toward walk-on parts and single-scene roles. He also took small parts outside Sandler-led or Sandler-produced projects, including Never Been Kissed, Late Last Night and Heavyweights. His one leading film role arrived with the 2006 comedy Grandma’s Boy, on which Sandler served as an executive producer. The film gave Covert a rare opportunity to move from dependable supporting player to the center of the story. His career is just as notable behind the camera. At Happy Madison Productions, Covert worked as an executive producer and occasional co-writer on many of the company’s films. He also contributed to Sandler’s comedy albums and frequently received co-songwriting credits for original songs performed in the movies. After Leo was released in 2023, Covert departed Happy Madison following a three-year hiatus to focus on a family situation. He has since discussed plans to establish his own production company, with the goal of helping theatrically released R-rated comedies return. Covert also cofounded Cherry Tree Books, a publisher of children’s eBooks.