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Master thief Max Burdett ([[Pierce Brosnan]]) and his beautiful accomplice, Lola Cirillo ([[Salma Hayek]]), steal the second of three famous diamonds, known as the [[Napoleon]] diamonds, from FBI Agent Stanley P. Lloyd ([[Woody Harrelson]]). But Lloyd shoots Max before passing out from being gassed by the thieves. Max survives and tells Lola to get the diamond. She does, leaving in its place the one-dollar bill that she had received as a tip for washing the agents' windshield (while in disguise). Max and Lola then fly to [[Paradise Island]] in [[The Bahamas]].
Agent Stanley P. Lloyd shows up 6 months later and accuses Burdett of planning to steal the third Napoleon diamond, which is on a cruise ship that will be docking for a week on the island. He denies this, and unwittingly turns the tables and befriends the frustrated detective Lloyd, showing him the pleasures that Paradise Island has to offer, even paying for the most expensive suite, the bridge suite, for as long as Lloyd is there. Lloyd, out of his element, adapts quickly to the easy-going [[Caribbean]] lifestyle and partners up with
Burdett, still wanting the diamond for himself, pretends to work with Mooré, and gives him a fake plan as to how he would steal the diamond (which he had earlier related to Stan), having no trouble keeping ahead of his nemesis in the meantime. Lola kicks Max out after he breaks his promise to spend their first sunset on her new deck she had been working on and after she finds out he lied about writing his vows to her. Max is forced to bunk with Stan, and they share their thoughts about each other's lives. The next morning, the authorities and Sophie discover them, revealing that Stan's FBI license is suspended. They team up to win back
The next day, Max is met by Stan while celebrating, who reveals he set him up and let Max do all the work while he later recovered the diamond. Max concedes that his nemesis has won this time, and is simply happy to live out his life with Lola, watching sunsets with her. As Max and Lola are enjoying themselves on the beach, Max uses a remote control on Stan's car that has arrived at the airport, using it to mess with Stan, who quickly realizes what is going on and is unable to do anything about it. Lola asks Max if this is the "last time", which he agrees to.
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