cast
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Adam Sandler
Michael Newman
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Kate Beckinsale
Donna Newman
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Christopher Walken
Morty
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David Hasselhoff
Ammer
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Henry Winkler
Ted
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Julie Kavner
Trudy
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Sean Astin
Bill
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Joseph Castanon
Ben at 7 years old
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Jonah Hill
Ben at 17 years old
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Jake Hoffman
Ben at 22-30 years old
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Tatum McCann
Samantha at 5 years old
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Lorraine Nicholson
Samantha at 14 years old
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Katie Cassidy
Samantha at 27 years old
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Cameron Monaghan
Kevin O'Doyle
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Jennifer Coolidge
Janine
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Rachel Dratch
Alice / Alan
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Sophie Monk
Stacy
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Michelle Lombardo
Linda
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Jana Kramer
Julie
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Nick Swardson
Bed, Bath & Beyond Guy
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Sidney Ganis
Dr. Bergman
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Michael Yama
Watsuhita Head Executive
- Mio Takada Watsuhita Executive
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Eiji Inoue
Watsuhita Executive
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Toshi Toda
Watsuhita Executive
- George K. Eguchi Ancient Executive
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Katheryn Cain
Kirsten
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Frank Coraci
Male Nurse
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Tim Herlihy
Doctor
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Iryna Blokhina
Jogger
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Emilio Cast
Michael at 10 Years Old
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Willy Goldstein
Lakeside Camp Boy
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Lily Mo Sheen
Lakeside Camp Girl
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Carolyn Hennesy
Kathy O'Doyle
- Elena Patten Samantha's Friend
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Cheyenne Alexis Dean
Samantha's Friend
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Elliott Cho
Ping Woo
- Alan Au Ping Woo's Father
- Ryan Keiser Firecracker Teen
- Christopher Levy Firecracker Teen
- Nickole Reyes Firecracker Teen
- Brianna Davis Firecracker Teen
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Robert Jones
Firecracker Teen
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Jenae Altschwager
Judy
- Manish Goyal Habeeboo Entourage
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Marco Khan
Habeeboo Entourage
- Ahmad Jordan Habeeboo Entourage
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Nick Hodaly
Habeeboo Entourage
- Alireza Tanbakoochi Habeeboo Entourage
- John Pagano Bandleader
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Dolores O'Riordan
Singer
- Sally Insul Aunt Peggy
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Rob Schneider
Prince Habeeboo (uncredited)
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Billy Slaughter
Newman Employee (uncredited)
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James Earl Jones
Narrator of Michael's Past (voice) (uncredited)
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Theresa Barrera
Susie (uncredited)
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Elizabeth DeCicco
Hot Assistant (uncredited)
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Abra Chouinard
Hot Employee (uncredited)
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Terry Crews
Singing Driver (uncredited)
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Howard Fong
Ping Woo's Grandfather (uncredited)
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Jorge Garcia
Ammer in SAP scene (uncredited)
- Tracy Britton Office Worker (uncredited)
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Jason Sandler
Best Man (uncredited)
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Celeste Thorson
Punk Chick (uncredited)
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Lana Titov
Wedding Guest (uncredited)
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Kyle Brody
Lakeside Camp Boy (uncredited)
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Blake Clark
Roy (uncredited)
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Lowe Cunningham
Young Mother (uncredited)
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Freddie De Grate
Segue Guy (uncredited)
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Betsy Hammer
Singer (uncredited)
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Dalon Huntington
Vendor (uncredited)
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Jen Johnson
Bikini Girl (uncredited)
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Spencer Kayden
Bar Patron (uncredited)
- Samantha Kelly Wedding Guest (uncredited)
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Traycee King
Bar Patron (uncredited)
- Karen Levine Sexual Harasser (uncredited)
- Kat Lombard Ex-Girlfriend Tamara (uncredited)
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Anna Lunberry
Bar Patron (uncredited)
- Mark Mahoney Waiter (uncredited)
- Danny McKinnon Max (uncredited)
- Shane Ralston Parking Attendant (uncredited)
- Alexandra Sullivan Supermodel (uncredited)
- C. Michelle Woods Ex-Girlfriend (uncredited)