Hollywood celebrities are infamous for jumping into the sack with no preamble and just as quickly, discarding their significant others as easily as a piece of used tissue. And for this reason, broken relationships, separation, and divorce run rampant in the entertainment world. It’s all in the circumstances really, because celebs are surrounded by so much temptation and superficiality. And because birds of a feather flock together, it’s but natural that these beautiful people gravitate towards equally beautiful people from the same industry.
Many male celebrities have been deemed crazy lucky by the public for having landed some of the most desirable women in Hollywood at one point in their lives or another. Some relationships have stood the test of time (at least by Hollywood standards) and others fizzled out as quickly as they started. But the fact of the matter is, these men have had the privilege of putting the names of the sexiest women in Hollywood in their little black books.
13 Jason Sudeikis (engaged to Olivia Wilde)
12 Jay-Z (married to Beyonce)
11 Sean Penn (dating Charlize Theron)
10 Brian Austin Green (married to Megan Fox)
9 Andrew Garfield (dated Emma Stone)
8 Justin Timberlake (dated Cameron Diaz, married Jessica Biel)
7 Ashton Kutcher (married Demi Moore, engaged to Mila Kunis)
6 Jake Gyllenhaal (dated Reese Witherspoon and Taylor Swift)
5 Chris Martin (married Gwyneth Paltrow, rumored to be dating Jennifer Lawrence)
4 Ryan Reynolds (married Scarlett Johansson, then Blake Lively)
3 Ryan Gosling (dated Sandra Bullock, Rachel McAdams, and Eva Mendes)
2 Ben Affleck (dated Gwyneth Paltrow, engaged to Jennifer Lopez, married Jennifer Garner)
1 Brad Pitt (dated Gwyneth Paltrow, married Jennifer Aniston, then Angelina Jolie)
He’s been considered one of Hollywood’s sexiest men for nearly three decades and at 51 years old, Brad Pitt still has that appeal that makes women swoon. So is it any surprise that such a specimen has dated women who are equally appealing? Many may have forgotten that he was once engaged to Gwyneth Paltrow, whom he met on the set of the film, Seven. He purportedly broke Paltrow’s heart when the engagement ended, but he didn’t waste time in moving on. He began dating Jennifer Aniston a year later and the two married in 2000. Of course, we all know how and why that marriage eventually ended. Pitt admitted that he fell in love with Angelina Jolie on the set of the film, Mr. and Mrs. Smith, when he was still very much a married man. Needless to say, he ended things with Aniston before he started up with Jolie, who is the mother of his six children.
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