Guest Stars Graham Rogers as Jacob "Smitty" Smith Alyssa Diaz as Teresa Alan Alda as Dr. Arthur Amiot Andrew Rothenberg as Father Danny O'Connor Josh Hamilton as Kevin Sullivan Austin Hébert as Young Jim Sullivan Bill Heck as Young Mickey Donovan Christopher Gray as Young Ray Donovan Amanda Michalka as Young Abby Carolyn Braver as Colleen Heidi Armbruster as Evelynne Chris Petrovski as Young Sean Walker David Patrick Kelly as Matty Gleason Danny Deferrari as Young Ezra Co Starring Alessandra Gleason as Maria Donovan Mackenzie Gleason as Maria Donovan Tye Alexander as Arty Nathaniel Beal as Mark Emily Rose Richardson as Teen Bridget Donovan Skyler Gallun as Teen Terry Donovan Ryan T. Connors as Older Teen Bunchy Craig Geraghty as Ted Johnny Sanchez as First AD Cliff Moylan as Milos Chad Knorr as Pete Connolly Mick O'Rourke as Jerry Gorman Gys de Villiers as Movie Director Tony Vincent as Movie Villain Freddy Heck as Five Year Old Ray Jason Iannacone as Spiros The Greek