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Slide 3 of 11

Jude Law

Back in the day, Jude Law and Sienna Miller were quite the "it" couple. That is, until he took his Alfie onscreen playboy for a test run off screen and had an affair with Daisy Wright, his kids' nanny! (Wait, didn't he play a cheater in 2004's Closer, too? Man, he was made for those parts!) In July 2005, Daisy gave a tell-all to British newspaper, the Sunday Mirror; Sienna called off the engagement; and Jude apologized for his bad behavior. While the couple did the on-and-off thing beginning in August 2005, by November 2006 they decided to call it quits for good. And somehow, Jude hasn't looked as steamy since. Sigh!

Photo: Kambouris/WireImage
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