Plot: Pendelton "Penny" Wise is a smooth-talking con-artist who makes a living by scamming people with phony travel comp vacations over the phone when, desperate for more fast cash, he's called to work for a shady, veteran con businessman, named Kelly Grant, in selling property for a gold mine over the phone, which takes a turn when Penny begins a relationship with Grant's mistress Caitlin, where Penny throws common sense and caution to the wind to woo her, while we wonder who is scamming who here.
Alternative Plot: Pendleton Wise (Vince Vaughn) is a suspicious sort, probably because he earns his living pitching travel scams. His cubicled existence is interrupted by the reemergence of Kelly Grant (Ed Harris), an infamous "room-runner" who, along with lover and business partner Caitlin (Julia Ormond), 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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