In the 1950s, brothers Jacey and Doug Holt, who come from the poorer side of their sleepy Midwestern town, vie for the affections of the wealthy, lovely Abbott sisters. Lady-killer Jacey alternates between Eleanor and Alice, wanting simply to break the hearts of rich young women. But sensitive Doug has a real romance with Pamela, which Jacey and the Abbott patriarch, Lloyd, both frown upon.
| Actor | Role |
|---|---|
 Joaquin PhoenixDoug Holt | Doug Holt |
 Liv TylerPamela Abbott | Pamela Abbott |
 Jennifer ConnellyEleanor Abbott | Eleanor Abbott |
 Billy CrudupJacey Holt | Jacey Holt |
 Joanna GoingAlice Abbott | Alice Abbott |
 Kathy BakerHelen Holt | Helen Holt |
 Will PattonLloyd Abbott | Lloyd Abbott |
 Michael SuttonSteve | Steve |
 Garrett M. BrownWebb Crosby | Webb Crosby |
 Barbara WilliamsJoan Abbott | Joan Abbott |
 Alessandro NivolaPeter Vanlaningham | Peter Vanlaningham |
| NNicole M. VassalloGiggling Girl #1 | Giggling Girl #1 |
| AAmanda ShermanGiggling Girl #2 | Giggling Girl #2 |
 Shawn HatosyVictor | Victor |
 Julie BenzCo-ed | Co-ed |
 Zoe McLellanSandy | Sandy |
| DDavid FrazierTed | Ted |
| MMargaret AshStore Clerk | Store Clerk |
 Clive RosengrenPrincipal | Principal |
 Susan BarnesMrs. Porter | Mrs. Porter |
| AAndrea PostWaitress | Waitress |
| JJack CumminsFuneral Director | Funeral Director |
| DDavid HeckendornPre-Record Singer | Pre-Record Singer |
 Michael KeatonNarrator/Older Doug Holt (uncredited) | Narrator/Older Doug Holt (uncredited) |