He played Skeeter Bronson in the 2008 Disney fantasy-comedy film Bedtime Stories, which was also his first appearance in a family-oriented film. He also guest-starred as himself in the Jessie episode "Punched Dumped Love" (the episode's title is a spoof of one of Sandler's own movies, Punch Drunk Love). He also played the title role of Robert 'Bobby' Boucher Jr. in the 1998 Touchstone Pictures sports comedy film, The Waterboy. He was mentioned in an episode of Liv & Maddie and the A.N.T. Farm episode "Animal HusbANTry".
He is also the husband of actress Jackie Sandler.