Continuity mistake: When there is an overhead shot inside of Winthrop's house when Billy Ray is giving a party, look down on the right hand side - a lady in a black dress is passed out, with her legs draped over a guy's lap. The next scene is a close up, and she's now lying against his chest (head first), then the next scene, she's back lying at the other end of the couch with her legs draped over his lap.
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Answer: The Duke brothers would have arranged all that as part of their "experiment." Since they had no idea of the plan to con them, Billy Ray's credentials would still be valid.