Steve Barron
Director
Jonathan Penner
as
Captain Air Traffic
Adam Sandler
as
Carmine
Julia Sweeney
as
Principal
Kevin Nealon
as
Senator
Adam Sandler
as
Self
Ed Sheeran
as
Self
Eminem
as
Self - Host
Devon Sawa
as
Stan
Henry Winkler
as
Coach Klein
Lawrence Gilliard Jr.
as
Derek Wallace
Adam Sandler
as
Robert 'Bobby' Boucher Jr.
Rob Schneider
as
Townie
Adam Sandler
as
Billy Madison
Darren McGavin
as
Brian Madison
Chris Farley
as
Bus Driver
Steve Buscemi
as
Danny McGrath
Dennis Dugan
Director
Leslie Mann
as
Corinne Maloney
Steve Buscemi
as
Homeless Guy
Adam Sandler
as
Sonny Koufax
Jackie Sandler
as
Waitress
Dennis Dugan
Director
Helena Yea
as
Chinese Lady
Ben Stiller
as
Hal L. - Orderly in Nursing Home
Adam Sandler
as
Happy Gilmore
Kevin Nealon
as
Potter
Ben Safdie
Director
Tilda Swinton
as
Anne 'Adley's Auction Manager'
Natasha Lyonne
as
Boston Player Personnel
Adam Sandler
as
Howard Ratner
Kyle Newacheck
Director
Margaret Qualley
as
Ben Stiller
as
Hal L.
Adam Sandler
as
Happy Gilmore
Julie Bowen
as
Virginia Venit
Peter Segal
Director
Adam Sandler
as
Dave Buznik
Woody Harrelson
as
Galaxia / Security Guard Gary
Luis Guzmán
as
Lou
Kevin Nealon
as
Sam
Adam Sandler
as
Danny Friedman
Luis Guzmán
as
Eli Katz
Jackie Sandler
as
Gabi Rodriguez Katz
Jackie Hoffman
as
Irene
Paul Thomas Anderson
Director
Adam Sandler
as
Barry Egan
Luis Guzmán
as
Lance
Emily Watson
as
Lena Leonard
Don McManus
as
Plastic