Sean Anders Director Adam Sandler Donny Actor, Producer Andy Samberg Todd Actor Leighton Meester Jamie Actor James Caan Father McNally Actor Vanilla Ice Self Tony Orlando Steve Spirou Actor Will Forte Phil Actor Milo Ventimiglia Chad Actor Susan Sarandon Mary McGarricle (Present Day) Actor Blake Clark Gerald Actor Nick Swardson Kenny Actor Eva Amurri Martino Mary McGarricle Actor Meagen Fay Helen Actor Ana Gasteyer Mrs. Ravensdale Actor Rachel Dratch Phil's Wife Actor Peggy Stewart Grandma Delores Actor Justin Weaver Young Donny Actor Todd Bridges Self David Caspe Screenwriter Jack Giarraputo Producer Heather Parry Producer Allen Covert Producer Barry Bernardi Executive Producer John Morris Executive Producer Dennis Dugan Executive Producer Tim Herlihy Executive Producer Brandon Trost Cinematographer Aaron Osborne Production Design Tom Costain Film Editing Rupert Gregson-Williams Original Music Erin Cochran Art Director Jennifer Gentile Set Decoration Ellen Lutter Costume Design Rachel Tenner Casting