Loren Dean

as Mumford

Hope Davis

as Sofie Crisp

Jason Lee

as Skip Skipperton

Alfre Woodard

as Lily

Zooey Deschanel

as Nessa Watkins

Mary McDonnell

as Althea Brockett

Pruitt Taylor Vince

as Henry Follett

Martin Short

as Lionel Dillard

David Paymer

as Dr. Ernest Delbanco

Jane Adams

as Dr. Phyllis Sheeler

Dana Ivey

as Mrs. Crisp

Kevin Tighe

as Mr. Crisp

Ted Danson

as Jeremy Brockett

Elisabeth Moss

as Katie Brockett

Robert Stack

as Himself

Jason Ritter

as Martin Brockett

Holt McCallany

as Newcomer

Simon Helberg

as College Roommate

David Doty

as Samuel Gorbeck