He married Kathryn Ashley Hagstrom on February 14, 2006. In July 2019, Hagstrom filed for divorce; it was finalized in November 2019.[4][5]
Career
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 four films that neither star nor are produced by Sandler: Never Been Kissed, Late Last Night, Heavyweights, and The Cable Guy.
Although Covert's on-screen presence has been reduced in recent years, he has continued to serve an active role in Sandler's movie production company, Happy Madison Productions, where Covert is 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.
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 is a cofounder of Cherry Tree Books, a publisher of eBooks for children.[6]