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

Meagen Fay

Helen

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

Erin Andrews

Randall Morgan's Receptionist

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 NGom

Father Shakalu

Baron Davis

Gym Coach

Amber Paul

Halo Stripper

Brad Grunberg

Tubby Tuke

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)