Adam Sandler as Donny Berger

Andy Samberg as Todd Peterson

Leighton Meester as Jamie Martin

Vanilla Ice as Vanilla Ice

Tony Orlando as Steve Spirou

Will Forte as Phil

Milo Ventimiglia as Chad

Susan Sarandon as Mary McGarricle (Present Day)

James Caan as Father McNally

Blake Clark as Gerald

Nick Swardson as Kenny

Eva Amurri as Ms. McGarricle

Meagen Fay as Helen

Ana Gasteyer as Mrs. Ravensdale

Rachel Dratch as Phil's Wife

Peggy Stewart as Grandma Delores

Luenell as Champale

Ciara as Brie

Justin Weaver as Young Donny

Todd Bridges as Todd Bridges

Dan Patrick as Randall Morgan

Rex Ryan as Jim Nance

Dana Goodman as Bridesmaid

Julia Lea Wolov as Bridesmaid

Rebecca Marshall as Bridesmaid

Abigail Klein as Bridesmaid

Carrie Wiita as Bridesmaid

Jackie Sandler as Masseuse

Erin Andrews as Randall Morgan's Receptionist

Sam Kaufman as School Buddy #1

Danny Mendelson as School Buddy #2

Colin Quinn as Strip Club DJ

Peter Dante as Dante Spirou

Rao Rampilla as Convenience Store Owner

Patty Ross as Judge

Chris Titone as Hotel Desk Clerk #1

J.D. Donaruma as Hotel Desk Clerk #2

Alan Thicke as TV Version Donny's Dad

Ian Ziering as TV Version Donny

Mike Sandler as Rabbi

Sadie Sandler as Lemonade Stand Kid

Sunny Sandler as Lemonade Stand Kid

Abdoulaye N'Gom as Father Shakalu

Baron Davis as Gym Coach

Amber Paul as Halo Stripper

Brad Grunberg as Tubby Tuke

Dennis Dugan as School Janitor

Allen Zwolle as Principal

Nancy Yee as Maid

Koji Kataoka as Butler

Jason Venezia as Naked Guy in Car

Kristen Valinch as Naked Lady in Car

Sheriden Thomas as Female Gym Teacher

Claude Tondreau as Class President Candidate

Michael J. Cammilleri as Jazz Trio at Party

Scott T. Beardsley as Jazz Trio at Party

Christian E. Boeger as Jazz Trio at Party

Sue Lee as Makeup Girl

Robert Harvey as Cocktail Party Guest

Paul Pabst as Producer Tom Kleinschmidt

Todd J. Fritz as Joey the Cameraman

Patrick S. O'Connor as Cameraman Charles Hornbeam Jr.

Andrew J. Perloff as Lou 'Boom Mic' Giamonna

Rich Eisen as Marathon Race Announcer

Darra Boyd as Wedding Guest (uncredited)

John Franchi as Drive-In Movie Goer (uncredited)

Colleen Kelly as Spa Manicurist (uncredited)

Kimberly Mae Waller as Student (uncredited)