Donny

Adam Sandler

Todd

Andy Samberg

Jamie

Leighton Meester

Father McNally

James Caan

Steve Spirou

Tony Orlando

Vanilla Ice

Vanilla Ice

Chad

Milo Ventimiglia

Phil

Will Forte

Gerald

Blake Clark

Mary McGarricle (Present Day)

Susan Sarandon

Helen

Meagen Fay

Phil's Wife

Rachel Dratch

Kenny

Nick Swardson

Mary McGarricle

Eva Amurri Martino

Grandma Delores

Peggy Stewart

Mrs. Ravensdale

Ana Gasteyer

Champale

Luenell

Brie

Ciara

Young Donny

Justin Weaver

Todd Bridges

Todd Bridges

Randall Morgan

Dan Patrick

Jim Nance

Rex Ryan

Bridesmaid

Dana Min Goodman

Bridesmaid

Dana Goodman

Bridesmaid

Julia Wolov

Bridesmaid

Julia Lea Wolov

Bridesmaid

Rebecca Marshall

Bridesmaid

Abigail Klein

Bridesmaid

Carrie Wiita

Masseuse

Jackie Sandler

Randall Morgan's Receptionist

Erin Andrews

School Buddy #1

Sam Kaufman

School Buddy #2

Daniel Mendelson

School Buddy #2

Danny Mendelson

Strip Club DJ

Colin Quinn

Dante Spirou

Peter Dante

Convenience Store Owner

Rao Rampilla

Judge

Patty Ross

Hotel Desk Clerk #1

Christopher Titone

Hotel Desk Clerk #2

J.D. Donaruma

TV Version of Donny's Dad

Alan Thicke

TV Version Donny

Ian Ziering

Rabbi

Mike Sandler

Lemonade Stand Kid

Sadie Sandler

Lemonade Stand Kid

Sunny Sandler

Father Shakalu

Abdoulaye N'Gom

Gym Coach

Baron Davis

Halo Stripper

Amber Paul

Tubby Tuke

Brad Grunberg

School Janitor

Dennis Dugan

Principal

Allen Zwolle

Maid

Nancy Yee

Butler

Koji Kataoka

Naked Guy in Car

Jason Venezia

Naked Lady in Car

Kristen Valinch

Female Gym Teacher

Sheriden Thomas

Class President Candidate

Claude Tondreau

Member of Jazz Trio at Party

Michael J. Cammilleri

Member of Jazz Trio at Party

Scott Beardsley

Jazz Trio at Party

Scott T. Beardsley

Member of Jazz Trio at Party

Christian E. Boeger

Makeup Girl

Sue Lee

Cocktail Party Guest

Robert Harvey

Producer Tom Kleinschmidt

Paul Pabst

Camera Crew Member

Randall Morgan

Joey the Cameraman

Todd J. Fritz

Joey the Cameraman

Todd Fritz

Cameraman Charles Hornbeam Jr.

Patrick S. O'Connor

Lou 'Boom Mic' Giamonna

Andrew J. Perloff

Cameraman Charles Hornbeam Jr.

Patrick O'Connor

Marathon Race Announcer

Rich Eisen

Wedding Guest (uncredited)

Darra Boyd

Drive-In Movie Goer (uncredited)

John Franchi

Spa Manicurist (uncredited)

Colleen Kelly

Student (uncredited)

Kimberly Mae Waller

Jessica

Kachina Dechert