Unless Darren can survive New York's largest drug mogul, write a paper on Dante's "Inferno," escape three thugs chasing the wrong guy and sell fifty pills of ecstasy to make his tuition payment, he'll never date the girl of his dreams.
| Actor | Role |
|---|---|
 Lou Taylor PucciDarren | Darren |
 Kristen BellGracie | Gracie |
 John HensleyColeman | Coleman |
 Nora ZehetnerMichelle | Michelle |
 Monica KeenaPetunia | Petunia |
 Diora BairdTiffany | Tiffany |
 Michael MasiniHalo | Halo |
 Rachel BostonLindsay | Lindsay |
| CChristopher M. BoydRichard | Richard |
 Jeffrey Nicholas BrownHomeless Joe | Homeless Joe |
 Michael PeñaEduardo | Eduardo |
| CCorrine CareyMarla | Marla |
 Jane LynchDoreen | Doreen |
 Curran ConnorScott | Scott |
| MMaya HazenBethany | Bethany |
 Chris JohnsonPaul | Paul |
 John KapelosHarold | Harold |
 Stephen KeysLittle Steve | Little Steve |
 Donnell RawlingsC-Low | C-Low |
 Paul SchackmanLouis | Louis |
 Daniel SpinkAlbert | Albert |
 Eddie Kaye ThomasRalphie | Ralphie |
| NNicholas ThomasRoger | Roger |
| JJohn C. MannHomeless Burt | Homeless Burt |
 Ron YuanThe Seoul Man | The Seoul Man |
 John Marshall JonesHousing Manager | Housing Manager |
 Jillian MurrayJayne | Jayne |