Story :After his long-time girlfriend dumps him, a thirty-year-old record store owner seeks to understand why he is unlucky in love while recounting his "top five breakups of all time".
Cast
John CusackRob Gordon
Iben HjejleLaura
Todd LouisoDick
Jack BlackBarry Judd
Lisa BonetMarie DeSalle
Catherine Zeta-JonesCharlie Nicholson
Joan CusackLiz
Tim RobbinsIan Raymond
Chris RehmannVince
Ben CarrJustin
Lili TaylorSarah Kendrew
Joelle CarterPenny Hardwick
Natasha Gregson WagnerCaroline Fortis
Shannon StilloAlison Jr. High
Drake BellRob Jr. High
Laura WhyteLaura's Mom
Sara GilbertAnaugh Moss
Rich TalaricoBarry's Customer
Matthew O'NeillBeta Band Customer
Brian PowellMiddle Aged Customer
Margaret TravoltaRob's Mom
Jillian PetersonLaura's Sister Jo
Dick CusackMinister
Susan YooGirl - 19 year old
Chris BauerPaul
K.K. DoddsMiranda
Marilyn Dodds FrankAlison's Mom
Duke DoyleKevin Bannister
Aaron HimelsteinBoy In Park
Jonathan HerringtonChris Thompson
Daniel Lee SmithRock Guy
Leah GaleMourner
David DarlowMourner
Erik GundersenMarco
Bruce SpringsteenBruce Springsteen
Alex DésertLouis
Alan S. JohnsonMan In Store
Ian BelknapParty Guest
Andrew MicheliParty Guest
Polly NoonanParty Guest
Philip Rayburn SmithParty Guest
Michele GraffParty Guest
Susie CusackParty Guest
Liam HayesPiano Player
Damian RogersGreenday Girl
Robert A. VillanuevaSkateboarder
Joe SpauldingFlea Market Musician
Scott A. MartinBartender
Heather NorrisLaura's Friend
Timothy W. TiedjeOperator (uncredited)
James AzraelGlam Rocker (uncredited)
Ian MichaelsGuy in Chem Lab (uncredited)
Susan HegartyLaura's Mom (voice) (uncredited)
Beverly D'AngeloWoman Selling Records (DVD version) (uncredited)