Dave Denali

Jay Harrington

Katherine

Julie Bowen

Lucy

Brooke Langton

Robert

Tom Parker

Christopher

Michael Ian Black

Matthew

Saul Rubinek

William

Corey Reynolds

John

Jay Paulson

Tom

Josh Cooke

Katherine's Secretary

Jim Rash

Anne

Jordana Spiro

Dave's Mom

Lee Garlington

Dave's Dad

Steve Ryan

Jameson

Greg Callahan

Benjamin

Reichen Lehmkuhl

Sandy

Wendel Meldrum

Howard

Allan Wasserman

Chad

Sean McGowan

Trent

Bru Muller

Robert's Attorney

Steve Hasley

Jonathan's Attorney

Christine Romeo

Sally

Jeanne Chinn

Pretty Woman

Shana Betz

Martha

Becky Meister

Bob Dalton

Jonathan Klein

Richard

Adam Harrington

Man in Sauna

Gerald Downey

Confused Waiter

Chris Dollard