Selma Blair

as Patti Petalson

Patrick Wilson

as Brian Callahan

Edward Burns

as Michael Murphy

Debra Messing

as Kate Scott

Dennis Farina

as Gilmore

Dara Coleman

as Silent Movie Actor

Heather Goldenhersh

as Sassy Party-Goer

Sarah Hudnut

as Scare-a Sara

Elizabeth Reaser

as Bernadette

Rosemarie DeWitt

as Murph's Hampton's Fling

Peter Van Wagner

as Mr. Sabatini

PT Walkley

as Singer / Songwriter

Bob Wiltfong

as Bookstore Representative

Donal Logue

as Chazz Coleman

Jay Patterson

as Michael's Agent

Peter Jacobson

as Monroe - Real estate agent

Joe Pistone

as Top Cat

Bill Hader

as Bill - Bookstore Fan