Jay Harrington
— Dave Denali
Julie Bowen
— Katherine
Brooke Langton
— Lucy
Tom Parker
— Robert
Michael Ian Black
— Christopher
Saul Rubinek
— Matthew
Corey Reynolds
— William
Jay Paulson
— John
Josh Cooke
— Tom
Jim Rash
— Katherine's Secretary
Jordana Spiro
— Anne
Lee Garlington
— Dave's Mom
Steve Ryan
— Dave's Dad
Greg Callahan
— Jameson
Reichen Lehmkuhl
— Benjamin
Wendel Meldrum
— Sandy
Allan Wasserman
— Howard
Sean McGowan
— Chad
Bru Muller
— Trent
Steve Hasley
— Robert's Attorney
John Antonini
— Jonathan Dodson
Christine Romeo
— Jonathan's Attorney
Jeanne Chinn
— Sally
Kellynn Jones
— Matthew's Secretary
Shana Betz
— Pretty Woman
Greg Weinbrecht
— Neighbor
Becky Meister
— Martha
Jonathan Klein
— Bob Dalton
Chandler Hayes
— Singer
Walter Davis
— Saxophonist