During the film's climax, Post Malone makes a cameo as DJ Omar Grant, a flamboyantly dressed sports commentator who weighs in on Happy's final tournament. Post has been racking up film roles over the past few years with recent parts in Road House and This Is Me...Now: A Love Story and Dear Santa.

Yes, Eminem shows up in Happy Gilmore 2. He plays the famous heckler's son from the first movie, whose part was played by Joe Flaherty. As part of his role, Eminem makes fun of Happy on the golf course by calling him a "jackass," just like Happy's dad did in the movie.