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".
Top Cast
JO
John CusackRob Gordon
IB
Iben HjejleLaura
TO
Todd LouisoDick
JA
Jack BlackBarry Judd
LI
Lisa BonetMarie DeSalle
CA
Catherine Zeta-JonesCharlie Nicholson
JO
Joan CusackLiz
TI
Tim RobbinsIan Raymond
CH
Chris RehmannVince
BE
Ben CarrJustin
LI
Lili TaylorSarah Kendrew
JO
Joelle CarterPenny Hardwick
NA
Natasha Gregson WagnerCaroline Fortis
SH
Shannon StilloAlison Jr. High
DR
Drake BellRob Jr. High
LA
Laura WhyteLaura's Mom
SA
Sara GilbertAnaugh Moss
RI
Rich TalaricoBarry's Customer
MA
Matthew O'NeillBeta Band Customer
BR
Brian PowellMiddle Aged Customer
MA
Margaret TravoltaRob's Mom
JI
Jillian PetersonLaura's Sister Jo
DI
Dick CusackMinister
SU
Susan YooGirl - 19 year old
CH
Chris BauerPaul
K.
K.K. DoddsMiranda
MA
Marilyn Dodds FrankAlison's Mom
DU
Duke DoyleKevin Bannister
AA
Aaron HimelsteinBoy In Park
JO
Jonathan HerringtonChris Thompson
DA
Daniel Lee SmithRock Guy
LE
Leah GaleMourner
DA
David DarlowMourner
ER
Erik GundersenMarco
BR
Bruce SpringsteenBruce Springsteen
AL
Alex DésertLouis
AL
Alan S. JohnsonMan In Store
IA
Ian BelknapParty Guest
AN
Andrew MicheliParty Guest
PO
Polly NoonanParty Guest
PH
Philip Rayburn SmithParty Guest
MI
Michele GraffParty Guest
SU
Susie CusackParty Guest
LI
Liam HayesPiano Player
DA
Damian RogersGreenday Girl
RO
Robert A. VillanuevaSkateboarder
JO
Joe SpauldingFlea Market Musician
SC
Scott A. MartinBartender
HE
Heather NorrisLaura's Friend
TI
Timothy W. TiedjeOperator (uncredited)
JA
James AzraelGlam Rocker (uncredited)
IA
Ian MichaelsGuy in Chem Lab (uncredited)
SU
Susan HegartyLaura's Mom (voice) (uncredited)
BE
Beverly D'AngeloWoman Selling Records (DVD version) (uncredited)