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

Mark O'Keefe Producer, Writer Jack Giarraputo Producer Neal H. Moritz Producer Jim Rygiel Visual Effects Designer Rupert Gregson-Williams Original Music Composer Dean Semler Director of Photography Frank Coraci Director Gary A. Hecker Foley Artist Max Daniels Stunts Rick Baker Special Effects Makeup Artist Kazu Hiro Prosthetic Supervisor J.J. Perry Stunts John Collins Assistant Art Director Adam Sandler Producer Bill Corso Prosthetic Makeup Artist Tim Herlihy Executive Producer Perry Andelin Blake Production Design Vanessa Motta Stunts Blake Neely Conductor Josh King First Assistant Director Roger Mussenden Casting Clinton Wayne Prosthetic Makeup Artist