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Cast Adam Goldberg ..... Phil Balow Amber Valletta ..... Brynn Lilly Angela Moore ..... Dental Receptionist Anysha Berthot ..... Leah Ben Affleck ..... Jack Giamoro Benjamin Ratner ..... Dr. Kevin Sands Brenda James ..... Judge Ellen Masters Damien Wayans ..... Lucky Reynolds Dustin Milligan ..... Young Dooley Gina Gershon ..... Arlene Kreiner Howard Hesseman ..... Ben Giamoro Jerry O'Connell ..... David Lilly John Cleese ..... Dr. Primkin Kal Penn ..... Alan Fineberg Kathleen Mullan ..... Agency Receptionist Keri Horton ..... Young Arlene Laura Soltis ..... Barbara Giamoro Lewis Broatch ..... Young Jack - Age 12 Ling Bai ..... Barbi Ling Mike Binder ..... Morty Rebecca Romijn ..... Nina Giamoro Samuel Ball ..... Jimmy Dooley Scott London ..... Young Jack - Age 19 to 22 Spencer Forbes ..... Anthony Giamoro

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