On a deserted back road in Alabama, Jack and Stephanie find themselves driving fast and running late. Their world suddenly changes when a strange accident leaves them stranded with no car, no cell phone coverage, and no help in sight. They have no choice except to continue on foot. As darkness approaches, they round a bend and see a small sign at the top of a long gravel driveway: The Wayside Inn.
The exhausted couple stands in front of an inviting house, complete with gated stone wall, ancient oak trees, and a note welcoming weary travelers. Inside they find another couple with an equally troubling story about a similar accident. It seems that backwoods pranksters have made their day miserable. Still, they are safe 0r so they think.
Richie (Justin Timberlake), a Princeton college student who pays for school with online gambling, bottoms out and travels to Costa Rica to confront the mastermind, Ivan (Ben Affleck), whom he believes has swindled him.
Ivan sees a kindred spirit in Richie and brings the younger man into his operation. When Richie comes to fully understand the deviousness of his new boss, he tries to turn the tables on him.
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