Adam Sandler as Happy Gilmore, a high - strung former hockey player who discovers a unique talent for golf. Christopher McDonald as Shooter McGavin, an arrogant golfer who is one of the top stars of the Pro Golf Tour. Julie Bowen as Virginia Venit, a public relations director for the Pro Golf Tour who becomes Happy 's romantic interest. Frances Bay as Grandma Gilmore. Carl Weathers as Chubbs Peterson, a pro golfer who was forced to retire early when his hand was bitten off by an alligator. Weathers reprises the role in Sandler 's 2000 film Little Nicky, despite Little Nicky being produced by New Line Cinema. Allen Covert as Otto, a homeless man who becomes Happy 's caddy. The character is unnamed in the film (although his name is revealed in a deleted scene but is listed in the end credits). Covert reprises the role in Sandler 's 2011 film Jack and Jill. Kevin Nealon as Gary Potter, an eccentric pro who Happy plays with in his first tournament. Peter Kelamis as Gary Potter 's caddy. Richard Kiel as Mr. Larson, Happy 's towering former boss. Dennis Dugan as Doug Thompson, the commissioner of the Pro Golf Tour. Joe Flaherty as Donald, an unruly fan hired by Shooter to distract Happy. Jared Van Snellenberg as Happy Gilmore 's caddy at the Waterbury Open. Will Sasso as mover Lee Trevino as himself Bob Barker as himself Verne Lundquist as himself Mark Lye as himself Ben Stiller as Hal L. (uncredited), the sadistic orderly running the nursing home
who plays the homeless caddy in happy gilmore
Allen Covert