Renée Zellweger as Anne Deveraux

Logan Lerman as George Devereaux

Kevin Bacon as Dan Devereaux

Troy Garity as Becker

David Koechner as Bill Massey

Eric McCormack as Charlie

Chris Noth as Dr. Harlan Williams

Molly C. Quinn as Paula

Nick Stahl as Bud

Mark Rendall as Robbie

J.C. MacKenzie as Tom

Phoebe Strole as Wendy

Steven Weber as Wallace McAllister

Robin Weigert as Hope

Dan John Miller as Mickey

Indra Ové as Diner Waitress

Joe Tunney as Car Salesman #2

Thomas C. Hessenauer as Henry the Doorman

Gwendolyn Briley-Strand as Bernice

Holly Palmer as Tanya

Rachel Specter as Sherry

Jerry Whiddon as NYC School Principal

John Badila as Banker

David DeBoy as Sales Manager

Kyle Prue as Boston Waiter

Aiden Hughes as Boston Maitre D'

Matthew Bowerman as Drama Teacher

Russ Widdall as Oliver Pierson

David Press as Pawnbroker

Veronica Taylor as Nancy

Michael Mack as Butler

Eddie Matz as West Penn Doorman

Jon Jolles as Carl

Cleo Pizana as Nate

Clay Steakley as Stage Manager

Anthony Addabbo as Frank

Steven Gonzalez as Police Officer

Tara Garwood as Diner Woman

Michael Gell as Diner Child

Bobby J. Brown as Diner Man

Lauren Klein as Mrs. Donahue

Stephen F. Schmidt as Joe Conner

Chris Kies as Painter Ted

Maury Ginsberg as Mr. Dillon

Laurien Clay as Oedipus Chorus Girl

Michael Traeger as St. Louis Principal

Susan Rome as Marla Massey

Mark Brutsche as Greeb

Michael Gable as Mr. Pelker

John B. Crye as Assistant Director

Paul L. Nolan as Marty Kamen

Rachel Weber as Judy

R. Scott Williams as Radford Teacher #2

Tony Abatemarco as Director

Jennifer Christopher as Candy / Mary Beth

Lindsay Rini as Teen Girl

Bill Allen as Medic

Sandy Racher as Cook

Vivienne Shub as Woman with Dog

Karen Carbone as Band Woman #1

Geoff Rock as Bellboy