Covert's first film role was a cruise ship bartender in Sandler's 1989 film
Going Overboard which also was Sandler's first cinematic appearance. Covert had minor parts in several subsequent Sandler films such as Otto the homeless caddy in
Happy Gilmore, before his first prominent role in 1998's
The Wedding Singer alongside Sandler and
Drew Barrymore. Covert would continue to have roles in Sandler's next four films, including one in
Little Nicky for which he gained 40 pounds. He eventually settled back into walk-on and single-scene appearances in Sandler's films beginning with
50 First Dates in 2004. In 2006, Covert starred in the comedy film ''
Grandma's Boy, his first (and only) lead role. Sandler served as an executive producer. Covert has also had small roles in films that neither star nor are produced by Sandler: Never Been Kissed, Late Last Night, and Heavyweights''. Although Covert's on-screen presence has been reduced in recent years, he has served an active role in Sandler's movie production company,
Happy Madison Productions, where Covert was an executive producer and sometimes co-writer on most of the company's films. In addition, Covert has contributed heavily to Sandler's many comedy albums, and frequently receives co-songwriting credits on the original songs that Sandler performs in many of his films. In 2023, after the release of
Leo, Covert departed from Happy Madison following a three-year hiatus to focus on a family situation. He has revealed plans to found his own production company, with a personal goal for a return of theatrically released R-rated comedy films. Meanwhile, he is currently involved with
Meemaw, an upcoming series starring
Roseanne Barr. Covert began appearing at
fan conventions in April 2024. Covert appeared as himself, along with Adam Sandler, in an episode of the television series
Undeclared. The show's creator,
Judd Apatow, is another friend and former college classmate of Covert and Sandler. Covert cofounded Cherry Tree Books, a publisher of
eBooks for children. == Filmography ==