6 Worst Celebrity Boyfriends Of All Time

Ericka Sóuter | Oct 12, 2012 Celebrities

chris brownAs soon as word got out that Rihanna and Chris Brown were really back together -- or at the very least publicly hooking up -- the same question went through everyone's mind: what the hell is she thinking? Yes, Chris Brown is talented. He can sing, he can dance. But can he be a good boyfriend? I think we all know the answer to that. If you are on the fence, just ask model Karrueche Tran, the girl he was dating when he and RiRi started fooling around again.

What is it about these notorious bad boys that makes them so appealing. Chris certainly isn't the only member of the scary celeb boyfriend club. So many stars treat their girlfriends like crap but still make it to the top of the hot, must-have bachelor list.

Check out 5 more of the worst celeb boyfriends of all time:


Image via Splash

  • Charlie Sheen


    Image via Matthew Straubmuller/Flickr


    He had the biggest and freakiest meltdown in Hollywood history and has a penchant for picking up prostitutes. Though tons of women swear the Anger Management star has loads of sex appeal. Guess he's still "winning."

  • John Mayer


    Image via Azimo/Flickr


    He's the king of kiss and tell. The singer blabbed about his sex life with one-time fling Jessica Simpson to Playboy magazine, calling her "sexual napalm" and saying she was "like crack cocaine to him" and he wanted to "snort her." And he held a press conference when he broke up with Jennifer Aniston. He totally humiliated both stars, yet he still lands other a-list girlfriends -- most recently Katie Perry.

  • Jude Law


    Image via Spojeni/Flickr


    What a cliche! Law cheated on longtime girlfriend Sienna Miller with his children's nanny. They split but eventually got back together for a brief reconcilation. That sordid past hasn't ended the trail of wannabe girlfriends.

  • Mel Gibson


    Image via Alan Light/Flickr


    Scary is an understatement. The Aussie actor's violent outrages are legendary. His ex Oksana Grigorieva taped him going into a crazed, profanity-filled rant that mad him sounds completely out of control. Yet ladies still love the Lethal Weapon star.

  • George Clooney


    Image via csztova/Flickr


    Okay, so he's not anything like the rest. But Gorgeous George landed on the list for his endless trail of broken hearts. So many sexy starlets try to get him to make the ultimate committment but they always end up a footnote in his romantic history. He's a total tease! That said, I bet even a month with him is worth the tears.

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