Anthony LaPaglia as Jim Winters

Aaron Stanford as Gabe Winters

Mark Webber as Pete Winters

Allison Janney as Molly Ripkin

Michelle Monaghan as Stacey

Brendan Sexton III as Robbie

Ron Livingston as Mr. Bricker

Ebon Moss-Bachrach as Steve

Frank Wood as Bill Brennan

Kel O'Neill as Tim

Thomas Sadoski as Chris Bender

Jason Fuchs as Bob

Lars Engstrom as Andrew

Welker White as History Teacher

Dana Segal as Math Teacher

Rocco Rosanio as Pete's Friend #1

Tim Dowlin as Pete's Friend #2

Kathleen Bridget Kelly as Mrs. Burton