Sandra Bullock as Gwen Cummings

Viggo Mortensen as Eddie Boone

Dominic West as Jasper

Elizabeth Perkins as Lily Cummings

Azura Skye as Andrea

Steve Buscemi as Cornell

Alan Tudyk as Gerhardt

Mike O'Malley as Oliver

Marianne Jean-Baptiste as Roshanda

Reni Santoni as Daniel

Diane Ladd as Bobbie Jean

Margo Martindale as Betty

Susan Krebs as Evelyn

Loudon Wainwright III as Guitar Guy

Katie Scharf as Young Gwen

Meredith Deane as Young Lily

Elizabeth Ruscio as Mom

Kathy Payne as Aunt Helen

Lisa Sutton as Dr. Stavros

Joanne Pankow as Saleslady / Night Tech

Corinne Reilly as Vanessa

Andrew Dolan as Groom

Maeve McGuire as Groom's Mother

Jim Moody as Chauffeur

Christina Chang as Bridesmaid

Adam Pervis as Younger Boy at Gas Station

Dan Byrd as Older Boy at Gas Station

Ric Reitz as Father at Gas Station

Suellen Yates as Andrea's Mother

Frank Hoyt Taylor as Equine Therapist

Brittani Warrick as Traci

Elijah Kelley as Darnell

Mike Dooly as Marty

Wendee Pratt as Elaine

Bill Anagnos as NY Cabdriver

Jack Armstrong as Falcon in Soap Opera

Judith Chapman as Deirdre in Soap Opera Cast

Suzanne Davis as Darian in Soap Opera

Rod McCary as Griffin Hartley in Soap Opera

Matt Cedeño as Bob Ramirez (uncredited)

Taber Cross as Rehab Patient (uncredited)

Bruno Gunn as Michael Anderson (uncredited)

Archie Hahn as Plant Shop Owner (uncredited)

Mark Heenehan as Miransh Wolfson (uncredited)

Christopher Murphy as Paul (uncredited)

Harsh Nayyar as Newsstand Vendor (uncredited)

Brent Ponder as Partier (uncredited)