Campbell Scott Director, Producer Denis Leary Bill Actor Hope Davis Ann Actor Maureen Anderman Supervisor Actor Jim Gaffigan Dayton Actor Earl Hindman Official Actor Christina Kirk Mary Actor J.C. MacKenzie Todd Actor Madison Arnold Bill's Father Actor Ezra Knight Lawyer Actor Caroline Kava Bill's Mother Actor Marin Hinkle Sherry Actor Seth Barrish Staff Member #1 Actor Tina Benko Blonde in Bar Actor Catherine Brophy Staff Member #2 Actor Bruce McIntosh Edward Actor, Writer Guy Davis Singer Actor, Original Music Gary Winick Producer Alexis Alexanian Producer Mary Frances Budig Producer Stephen P. Dunn Producer Jonathan Sehring Executive Producer Caroline Kaplan Executive Producer John Sloss Executive Producer Dan Gillham Cinematographer Andy Keir Film Editing John Brainard Art Director Chris Shriver Production Design Sam Hutchins First Assistant Director Toni Fusco Costume Design Ellen Lewis Casting Marcia DeBonis Casting Chad Lemieux Second Assistant Director