Jay Harrington as Dave Denali

Julie Bowen as Katherine

Brooke Langton as Lucy

Tom Parker as Robert

Michael Ian Black as Christopher

Saul Rubinek as Matthew

Corey Reynolds as William

Jay Paulson as John

Josh Cooke as Tom

Jim Rash as Katherine's Secretary

Jordana Spiro as Anne

Lee Garlington as Dave's Mom

Steve Ryan as Dave's Dad

Greg Callahan as Jameson

Reichen Lehmkuhl as Benjamin

Wendel Meldrum as Sandy

Allan Wasserman as Howard

Sean McGowan as Chad

Bru Muller as Trent

Steve Hasley as Robert's Attorney

John Antonini as Jonathan Dodson

Christine Romeo as Jonathan's Attorney

Jeanne Chinn as Sally

Kellynn Jones as Matthew's Secretary

Shana Betz as Pretty Woman

Greg Weinbrecht as Neighbor

Becky Meister as Martha

Jonathan Klein as Bob Dalton

Chandler Hayes as Singer

Walter Davis as Saxophonist

Dave Pelman as Bass Player

Adam Harrington as Richard

Gerald Downey as Man in Sauna

Chris Dollard as Confused Waiter

James Grimaldi as Michael