Michael Douglas as Ben Kalmen

Susan Sarandon as Nancy Kalmen

Danny DeVito as Jimmy Marino

Mary-Louise Parker as Jordon Karsch

Jenna Fischer as Susan Porter

Imogen Poots as Allyson Karsch

Jesse Eisenberg as Daniel Cheston

Richard Schiff as Steve Heller

Jake Siciliano as Scotty

David Costabile as Gary Porter

Ben Shenkman as Peter Hartofilias

Anastasia Griffith as Carol Salomonde

Alex Kaluzhsky as Ted Loof

Simona Williams as Nurse

James Colby as Sgt. John Haverford

Arthur J. Nascarella as Nascarella

Bruce Altman as Dr. Steinberg

Nick H. Toomey as Bill Rallye

Adam Pally as Irate Student

Lenny Venito as Todd The Building Manager

Greg McFadden as Maitre-D

Ricky Garcia as Waiter

Douglas McGrath as Dean Edward Gitleson

Gillian Jacobs as Tall Girl

Katherine Owens as Allyson's Attractive Friend

Arizona Muse as Kelly

Jolynn Carpenter as Hipster Model (uncredited)

Stephanie Danielson as Flirtatious Student (uncredited)

Brooklyn Decker as Woman Walking by Ben on the Bench (uncredited)

Bianca Giancoli as Jogger (uncredited)

Anna Kuchma as Student (uncredited)

Olivia Thirlby as Maureen (uncredited)

Lila Urda as Hipster (uncredited)