Covert's first film role, as a bartender, was in Sandler's 1989 film Going Overboard. He had minor parts in several subsequent Sandler films before his first prominent role in 1998's The Wedding Singer alongside Sandler and Drew Barrymore. Covert would continue to have fairly large roles in Sandler's next four films, including one in Little Nicky for which he gained 40 pounds. He eventually settled back into smaller walk-on and single-scene appearances in Sandler's films beginning with 50 First Dates in 2004. However, in 2006 Covert starred in the comedy film Grandma's Boy, his first (and only) lead role. Sandler didn't act in that film but served as an executive producer. Covert has also had small roles in four films that neither star or are produced by Sandler: Never Been Kissed, Late Last Night, Heavyweights, and The Cable Guy.