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| Vince Vaughn | Pendelton ``Penny'' Wise |
| Julia Ormond | Caitlin Carlson |
| Ed Harris | Kelly Grant |
| Rory Cochrane | Joel |
| Wallace Shawn | Gene |
| George Wendt | Archie |
| Stephen Tobolowsky | Mick |
| Jeanetta Arnette | Cheryl |
| Shishir Kurup | Sujat |
| Harper Roisman | Harry |
| Romany Malco Jr. | Zeke |
| Brian George | Nasser |
| Amber Benson | Batgirl |
Pendleton Wise is a suspicious sort, probably because he earns his living pitching travel scams. His cubicled existence is interrupted by the reemergence of Kelly Grant, an infamous ``room-runner'' who, along with lover and business partner Caitlin, offers Penny a spot as a top closer in a high stakes mining deal. When Penny and Caitlin start an affair, questions of who's screwing whom lead Penny into deeper waters than he'd anticipated.
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