James Caan
Father McNally
Susan Sarandon
Mary McGarricle (Present Day)
Luenell
Champale
Milo Ventimiglia
Chad
Vanilla Ice
Vanilla Ice
Dennis Dugan
School Janitor
Ian Ziering
TV Version Donny
Adam Sandler
Donny Berger
Peter Dante
Dante Spirou
Blake Clark
Gerald
Rachel Dratch
Phil's Wife
Nick Swardson
Kenny
Eva Amurri Martino
Ms. McGarricle
Jackie Sandler
Masseuse
Robert Harvey
Cocktail Party Guest
Koji Kataoka
Butler
Will Forte
Phil
Andy Samberg
Todd Peterson
Todd Bridges
Todd Bridges
Meagen Fay
Helen
Tony Orlando
Steve Spirou
Alan Thicke
TV Version Donny's Dad
Leighton Meester
Jamie Martin
Ana Gasteyer
Mrs. Ravensdale
Ciara
Brie
Brad Grunberg
Tubby Tuke
Dan Patrick
Randall Morgan
Peggy Stewart
Grandma Delores
Rebecca Marshall
Bridesmaid
Dana Goodman
Bridesmaid
John Franchi
Drive-In Movie Goer (uncredited)
Baron Davis
Gym Coach
Patty Ross
Judge
Abdoulaye NGom
Father Shakalu
J.D. Donaruma
Hotel Desk Clerk #2
Carrie Wiita
Bridesmaid
Julia Lea Wolov
Bridesmaid
Sadie Sandler
Lemonade Stand Kid
Justin Weaver
Young Donny
Rich Eisen
Marathon Race Announcer
Colin Quinn
Strip Club DJ
Sunny Sandler
Lemonade Stand Kid
Erin Andrews
Randall Morgan's Receptionist
Nancy Yee
Maid
Amber Paul
Halo Stripper
Chris Titone
Hotel Desk Clerk #1
Abigail Klein
Bridesmaid
Colleen Kelly
Spa Manicurist (uncredited)
Allen Zwolle
Principal
Rao Rampilla
Convenience Store Owner
Darra Boyd
Wedding Guest (uncredited)
Rex Ryan
Jim Nance