Guest Stars Sandy Martin as Sandy Patrick Kerry Condon as Molly Sullivan Quincy Tyler Bernstine as Detective Perry Peter Gerety as Jim Sullivan Austin Hébert as Young Jim Sullivan Bill Heck as Young Mickey Donovan Co Starring Tye Alexander as Arty Nathaniel Beal as Mark Aidan Pierce Brennan as Young Ray Donovan Craig Geraghty as Ted Danny Bolero as Roberto Kersti Bryan as Anne Donovan Peter Albrink as Young Billy Doyle Princess Adenike Ajibola as Young Claudette Christopher Halladay as Bartender Eric Reid Schroeder as Rooney Brinks Driver James Pravasilis as Young Larry O'Malley George Bartenieff as Gerald Moskovitz Chris Walker as Bernie Halsey Caesar Samayoa as Man 1