5. Thomas Crown (The Thomas Crown Affair)
Metro-Goldwyn-MayerThe 1998 remake of the 1968 film involved multi-millionaire Thomas Crown (Pierce Brosnan) who participates in a cat and mouse game with insurance investigator Catherine Banning (Rene Russo) as she attempts to discover how a $100 million painting was stolen from the Metropolitan Museum of Art. The majority of the film is Brosnan channeling 007 and looking awesome in a suit as Russo's Benning falls for him, because in that movie, it'd be impossible not to. The two instigate an illicit affair even though Benning knows full well Crown was responsible for the theft. The finale of the movie is where he earns his place on the list. In an elaborate bait and switch, he personally puts the painting back in its place in the museum right under the noses of both her and the entire police force, without getting caught. The best thing about all of this is the motivation: everything he does in the movie is for the fun of it. Seriously. There's a scene where he capsizes a million dollar catamaran because he likes the splash. If we had that kind of bank, we'd blow up cars in the back yard for fun too. Probably a good thing we don't.