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 Heidi Armbruster as Evelynne Carolyn Braver as Colleen David Patrick Kelly as Matty Gleason Danny Deferrari as Young Ezra Chris Petrovski as Young Sean Walker Co Starring Mackenzie Gleason as Maria Donovan Alessandra 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 Craig Geraghty as Ted Ryan T. Connors as Older Teen Bunchy Cliff Moylan as Milos Johnny Sanchez as First AD Chad Knorr as Pete Connolly Gys de Villiers as Movie Director Tony Vincent as Movie Villain Freddy Heck as Five Year Old Ray Mick O'Rourke as Jerry Gorman Jason Iannacone as Spiros The Greek