The clumsy and shy Stanley is a nice fellow, beloved by his colleagues in the office. He has a crush on the gorgeous new-hire Diana, but he has difficulties to get close to her. When Stanley finally invites Diana for a date, he hits the homeless Phil with his Taurus, and his planned night turns upside down.
| Actor | Role |
|---|---|
 Luke WilsonStanley | Stanley |
 Denise RichardsDiana | Diana |
 Jay LacopoPhil | Phil |
 Ben AffleckMichael | Michael |
 Phill LewisMitch | Mitch |
 Deborah TheakerNancy | Nancy |
 Melissa McCarthyMarilyn | Marilyn |
 Tim DeKaySpeaker | Speaker |
 Greg PittsTee | Tee |
 Wayne FedermanGlen Federman | Glen Federman |
 Mike SchwartzCo-Worker | Co-Worker |
 Neal MatarazzoNeal | Neal |
 Jim LauClerk | Clerk |
 Diana Maria RivaRose Lady | Rose Lady |
| BBlas LorenzoWaiter | Waiter |
 Buck KartalianOld Man | Old Man |
 Rachel WinfreeKnitting Lady | Knitting Lady |
| RRobert M. KochActor (Lincoln) | Actor (Lincoln) |
 Jason KravitsStage Manager | Stage Manager |
| JJeanette MillerElderly Woman | Elderly Woman |
 Kevin FarleyBus Driver | Bus Driver |
| MMarcus DeJohnBill | Bill |
| MMarilyn StaleyMary | Mary |
 Veena BidashaMahareinlu | Mahareinlu |
 David KoechnerCarl | Carl |
 Matthew MaherHank | Hank |
 Meredith SalengerSara | Sara |
 Bobby SlaytonDave Bowen | Dave Bowen |
 Phil ReevesBill Sykes | Bill Sykes |
| SSteven ShenbaumTed | Ted |