Sean Penn Jimmy Markum Tim Robbins Dave Boyle Kevin Bacon Sean Devine Laurence Fishburne Whitey Powers Marcia Gay Harden Celeste Boyle Laura Linney Annabeth Markum Kevin Chapman Val Savage Tom Guiry Brendan Harris Emmy Rossum Katie Markum Spencer Treat Clark Silent Ray Harris Adam Nelson Nick Savage Robert Wahlberg Kevin Savage Jenny O'Hara Esther Harris John Doman Driver Cameron Bowen Young Dave Connor Paolo Young Sean Cayden Boyd Michael Boyle Tori Davis Lauren Devine Jonathan Togo Pete Shawn Fitzgibbon Funeral Director Will Lyman FBI Agent Birden Celine du Tertre Nadine Markum Ari Graynor Eve Pigeon Zabeth Russell Diane Cestra Celeste Oliva Trooper Jenny Coughlin Bates Wilder Loud Mouth Cop