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