Adam Sandler Happy Gilmore Julie Bowen Virginia Christopher McDonald Shooter McGavin Benny Safdie Frank Manatee Ben Stiller Hal L Bad Bunny Oscar Mejías John Daly John Daly Dennis Dugan Doug Thompson Haley Joel Osment Billy Jenkins Lavell Crawford Slim Peterson Jackie Sandler Monica Sadie Sandler Charlotte Sunny Sandler Vienna Maxwell Jacob Friedman Gordie Philip Schneider Bobby Ethan Cutkosky Wayne Conor Sherry Terry Steve Buscemi Bad Neighbor Pat Kevin Nealon Gary Potter Kym Whitley Bessie John Farley Nate Eric André Steiner Martin Herlihy Fitzy Margaret Qualley Sally Verne Lundquist Verne Lundquist Post Malone DJ Omar Gosh Jack Giarraputo Jack Beard Eminem Donald Jr. Jon Lovitz Dapper Man Rob Schneider Tricycle Cowboy Dan Patrick Pat Daniels Stephen A. Smith Stephen A. Smith Chris Berman Chris Berman Oliver Hudson Harley Rebecca Quin Flex Jonathan Loughran Crazy Eye Orderly Jena Sims Screech Fan Helena Kid Cudi FBI Agent Sean Evans Sean Evans Bobby Lee Bobby Lee Andrew Santino Andrew Santino