Adam Sandler Michael Newman Kate Beckinsale Donna Newman Christopher Walken Morty David Hasselhoff Ammer Henry Winkler Ted Julie Kavner Trudy Sean Astin Bill 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 Toshi Toda Watsuhita Executive Frank Coraci Male Nurse Tim Herlihy Doctor Iryna Blokhina Jogger Willy Goldstein Lakeside Camp Boy Lily Mo Sheen Lakeside Camp Girl Carolyn Hennesy Kathy O'Doyle Cheyenne Alexis Dean Samantha's Friend Jenae Altschwager Judy Marco Khan Habeeboo Entourage Rob Schneider Prince Habeeboo (uncredited) Billy Slaughter Newman Employee (uncredited) James Earl Jones Narrator of Michael's Past (voice) (uncredited) Terry Crews Singing Driver (uncredited) Jorge Garcia Ammer in SAP scene (uncredited)