Adam Sandler as Michael Newman

Kate Beckinsale as Donna Newman

Christopher Walken as Morty

David Hasselhoff as Ammer

Henry Winkler as Ted

Julie Kavner as Trudy

Sean Astin as Bill

Joseph Castanon as Ben at 7 years old

Jonah Hill as Ben at 17 years old

Jake Hoffman as Ben at 22-30 years old

Tatum McCann as Samantha at 5 years old

Lorraine Nicholson as Samantha at 14 years old

Katie Cassidy as Samantha at 27 years old

Cameron Monaghan as Kevin O'Doyle

Jennifer Coolidge as Janine

Rachel Dratch as Alice / Alan

Sophie Monk as Stacy

Michelle Lombardo as Linda

Jana Kramer as Julie

Nick Swardson as Bed, Bath & Beyond Guy

Sidney Ganis as Dr. Bergman

Michael Yama as Watsuhita Head Executive

Mio Takada as Watsuhita Executive

Eiji Inoue as Watsuhita Executive

Toshi Toda as Watsuhita Executive

George K. Eguchi as Ancient Executive

Katheryn Cain as Kirsten

Frank Coraci as Male Nurse

Tim Herlihy as Doctor

Iryna Blokhina as Jogger

Emilio Cast as Michael at 10 Years Old

Willy Goldstein as Lakeside Camp Boy

Lily Mo Sheen as Lakeside Camp Girl

Carolyn Hennesy as Kathy O'Doyle

Elena Patten as Samantha's Friend

Cheyenne Alexis Dean as Samantha's Friend

Elliott Cho as Ping Woo

Alan Au as Ping Woo's Father

Ryan Keiser as Firecracker Teen

Christopher Levy as Firecracker Teen

Nickole Reyes as Firecracker Teen

Brianna Davis as Firecracker Teen

Robert Jones as Firecracker Teen

Jenae Altschwager as Judy

Manish Goyal as Habeeboo Entourage

Marco Khan as Habeeboo Entourage

Ahmad Jordan as Habeeboo Entourage

Nick Hodaly as Habeeboo Entourage

Alireza Tanbakoochi as Habeeboo Entourage

John Pagano as Bandleader

Dolores O'Riordan as Singer

Sally Insul as Aunt Peggy

Rob Schneider as Prince Habeeboo (uncredited)

Billy Slaughter as Newman Employee (uncredited)

James Earl Jones as Narrator of Michael's Past (voice) (uncredited)

Theresa Barrera as Susie (uncredited)

Elizabeth DeCicco as Hot Assistant (uncredited)

Abra Chouinard as Hot Employee (uncredited)

Terry Crews as Singing Driver (uncredited)

Howard Fong as Ping Woo's Grandfather (uncredited)

Jorge Garcia as Ammer in SAP scene (uncredited)

Tracy Britton as Office Worker (uncredited)

Jason Sandler as Best Man (uncredited)

Celeste Thorson as Punk Chick (uncredited)

Lana Titov as Wedding Guest (uncredited)

Kyle Brody as Lakeside Camp Boy (uncredited)

Blake Clark as Roy (uncredited)

Lowe Cunningham as Young Mother (uncredited)

Freddie De Grate as Segue Guy (uncredited)

Betsy Hammer as Singer (uncredited)

Dalon Huntington as Vendor (uncredited)

Jen Johnson as Bikini Girl (uncredited)

Spencer Kayden as Bar Patron (uncredited)

Samantha Kelly as Wedding Guest (uncredited)

Traycee King as Bar Patron (uncredited)

Karen Levine as Sexual Harasser (uncredited)

Kat Lombard as Ex-Girlfriend Tamara (uncredited)

Anna Lunberry as Bar Patron (uncredited)

Mark Mahoney as Waiter (uncredited)

Danny McKinnon as Max (uncredited)

Shane Ralston as Parking Attendant (uncredited)

Alexandra Sullivan as Supermodel (uncredited)

C. Michelle Woods as Ex-Girlfriend (uncredited)