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".
- BAFTA2001
- Golden Globes2000
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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".
| Actor | Role |
|---|---|
 John CusackRob | Rob |
 Iben HjejleLaura | Laura |
 Todd LouisoDick | Dick |
 Jack BlackBarry | Barry |
 Lisa BonetMarie De Salle | Marie De Salle |
 Catherine Zeta-JonesCharlie | Charlie |
 Joan CusackLiz | Liz |
 Tim RobbinsIan | Ian |
| CChris RehmannVince | Vince |
| BBen CarrJustin | Justin |
 Lili TaylorSarah | Sarah |
 Joelle CarterPenny | Penny |
 Natasha Gregson WagnerCaroline | Caroline |
| SShannon StilloAlison Jr. High | Alison Jr. High |
 Drake BellRob Jr. High | Rob Jr. High |
 Laura WhyteLaura's Mom | Laura's Mom |
 Sara GilbertAnaugh | Anaugh |
 Rich TalaricoBarry's Customer | Barry's Customer |
| MMatthew O'NeillBeta Band Customer | Beta Band Customer |
 Brian PowellMiddle Aged Customer | Middle Aged Customer |
 Margaret TravoltaRob's Mom | Rob's Mom |
 Jillian PetersonLaura's Sister Jo | Laura's Sister Jo |
| DDick CusackMinister | Minister |
 Susan YooGirl - 19 year old | Girl - 19 year old |
 Chris BauerPaul | Paul |
 K.K. DoddsMiranda | Miranda |
 Marilyn Dodds FrankAlison's Mom | Alison's Mom |
| DDuke DoyleKevin Bannister | Kevin Bannister |
 Aaron HimelsteinBoy In Park | Boy In Park |
| JJonathan HerringtonChris Thompson | Chris Thompson |