Adam Sandler
Donny Berger

Andy Samberg
Todd Peterson

Leighton Meester
Jamie Martin

Vanilla Ice
Vanilla Ice

Tony Orlando
Steve Spirou

Will Forte
Phil

Milo Ventimiglia
Chad

Susan Sarandon
Mary McGarricle (Present Day)

James Caan
Father McNally

Blake Clark
Gerald

Nick Swardson
Kenny

Eva Amurri
Ms. McGarricle

Ana Gasteyer
Mrs. Ravensdale

Rachel Dratch
Phil's Wife

Peggy Stewart
Grandma Delores

Luenell
Champale

Ciara
Brie

Justin Weaver
Young Donny

Todd Bridges
Todd Bridges

Dan Patrick
Randall Morgan

Rex Ryan
Jim Nance

Dana Goodman
Bridesmaid

Julia Lea Wolov
Bridesmaid

Rebecca Marshall
Bridesmaid

Abigail Klein
Bridesmaid

Carrie Wiita
Bridesmaid

Jackie Sandler
Masseuse

Sam Kaufman
School Buddy #1

Colin Quinn
Strip Club DJ

Peter Dante
Dante Spirou

Rao Rampilla
Convenience Store Owner

Patty Ross
Judge

Chris Titone
Hotel Desk Clerk #1

Alan Thicke
TV Version Donny's Dad

Ian Ziering
TV Version Donny

Sadie Sandler
Lemonade Stand Kid

Sunny Sandler
Lemonade Stand Kid

Abdoulaye N'Gom
Father Shakalu

Baron Davis
Gym Coach

Amber Paul
Halo Stripper

Dennis Dugan
School Janitor

Allen Zwolle
Principal

Nancy Yee
Maid

Koji Kataoka
Butler

Robert Harvey
Cocktail Party Guest

Rich Eisen
Marathon Race Announcer

Darra Boyd
Wedding Guest (uncredited)

John Franchi
Drive-In Movie Goer (uncredited)

Colleen Kelly
Spa Manicurist (uncredited)

Kimberly Mae Waller
Student (uncredited)