Adam Sandler
Happy Gilmore
Christopher McDonald
Shooter McGavin
Julie Bowen
Virginia Venit
Dennis Dugan
Doug Thompson
Jared Van Snellenberg
Happy's Waterbury Caddy
Rich Elwood
Assistant Coach
Andrew Johnston
Crowd Guy - Waterbury
Kim Restell
Crowd Girl - Waterbury
Fred Perron
Waterbury Heckler
Helen Honeywell
Crazy Old Lady
Paul Raskin
Starter #1 - Waterbury
William Samples
Starter #2 - AT&T
John Destry
Zamboni Driver
James Crescenzo
Shooter's AT&T Caddy
Brett Armstrong
Shooter's Tournament Caddy
Peter Kelamis
Potter's Caddy
Stephen Tibbetts
Pro Golfer
Donnie MacMillan
Young Happy
Louis O'Donoghue
Happy's Dad
Lisanne Collett
Happy's Mom
Stephen Dimopoulos
Italian Guy
Douglas Newell
Starter #4 - Pro-Am
Frank L. Frazier
Blue Collar Fan
Jessica Gunn
Signed Chest Woman
Michelle Holdsworth
Babe on Green
Charles L. Brame
Abe Lincoln
Elizabeth Duff
Golf Fan (uncredited)
Carrie Anne Fleming
Donna (uncredited)
Jack Giarraputo
Sportscaster (uncredited)
Brennan Kotowich
Boy (uncredited)
Michael Roberds
Shirtless 'H' Fan (uncredited)
Joe Sakic
Player at Hockey Tryouts (uncredited)
Ben Stiller
Hal L. - Orderly in Nursing Home (uncredited)
Valarie Trapp
Valarie Trapp (uncredited)
Heath Young
Golf Fan (uncredited)