Larry David as Nathan Flomm / Rolly DaVore

Jon Hamm as Will Haney

Kate Hudson as Rhonda

Eva Mendes as Jennifer

Danny McBride as Frank

Michael Keaton as Joe Stumpo

Liev Schreiber as Tibor (uncredited)

Bill Hader as Rags

Philip Baker Hall as McKenzie

Amy Ryan as Wendy

JB Smoove as Jaspar

Rick Malambri as Flirty Guy at Fair

Amy Landecker as Nathan's Wife

Mike Cerrone as Poker Buddy

Lenny Clarke as Poker Buddy

Peter Farrelly as Poker Buddy

Conan O'Brien as Conan O'Brien

Paul Scheer as Friend at Dinner