Odd Couples
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Evan Rachel Wood and Marilyn Manson
Sure, in the beginning of her career, Evan Rachel Wood gave off an edgy, dark-side vibe that was belied by her gorgeous, classical beauty. But still, anyone who dates the king of shock hard rock (years after his career has arguably fizzled) makes us scratch our heads. The couple started as friends, getting romantic after his divorce, despite a 17-year age difference. His ex-wife, Dita Von Teese, alluded to drug and rock star lifestyle issues as a reason for their breakup. We'll have to speculate about the reasons for his breakup with Wood, as she's stayed mum on specifics.
Image: Stefan Trautmann / WENN
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Katie Holmes and Tom Cruise
The Oprah couch incident will live on in pop culture infamy for a very long time. It cast Cruise's marriage to Holmes with a veil of trying-way-too-hard. In the end, skeptics were probably glad to hear the rumors that Holmes left abruptly, under cover of night, to escape the Scientology upbringing for which daughter Suri was destined. Who knows what went down for sure, but we're glad that Holmes and Cruise are now free to be themselves.
Image: Brian To/WENN.
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Lance Armstrong and Ashley Olsen
This one was short-lived, but in 2007 these two were spotted making out in NYC. What brought them together? We don't know, but given Armstrong's fall from grace, we can't say we're sorry it didn't work out.
Images: WENN.com; Ivan Nikolov/WENN.com
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Jennifer Lopez and Caspar Smart
They only recently broke up, but this long-term relationship had a lot of people wondering if she was just a sugar mama, and if this guy was happily playing the rebound. Over time it seemed they were legit, until they parted ways amidst rumors of Smart cheating, which he vehemently denies. Hopefully Lopez has another hottie in her backup crew to dance the night away with.
Image: WENN.com
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Mila Kunis and Macaulay Culkin
Kunis is now with Ashton Kutcher, making tons of Hollywood sense, given their onscreen love history. But prior to that, she was with the child star of the 90s for eight years. Since their breakup, Culkin has been plagued by tabloid rumors of ill health and drug use. Let's hope he's doing as well now as Kunis seems to be.
Image: WENN
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Mary Kate Olsen and Olivier Sarkozy
These two are currently engaged and none of us outside their inner circle gets it. We're hoping those on the inside do, at least. Sarkozy is French political royalty and Olsen is American fashion royalty, so perhaps their connection isn't so far off base. Fashion and France do go together like a wink and a smile.
Image: IZZY/WENN.com
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Jennifer Lopez and Ben Affleck
Bennifer! She's from the block and he's from the A-list actor world. How could these two ever last? They didn't (duh). We don't miss the constant tabloid fodder the relationship provided, and while they both have sung each other's praises since, Affleck and his current wife, Jennifer Garner, seem more on par.
Image: WENN
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Sarah Jessica Parker and Robert Downey Jr.
This is a major throwback couple. Before there was Matthew Broderick, there was RDJ in the 80s. The two dated for seven years, but in the end, both he and Parker have confirmed his addictive personality was the culprit.
Images: Pat Denton/WENN.com; Joseph Marzullo/WENN.com
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Chloe Green and Marc Anthony
Only recently broken up at the beginning of this year, Marc Anthony chose to move on from his most recent long-term relationship (with Jennifer Lopez, natch) with a younger partner. A lot younger. She's 21, he's 44. She's the heir to the Topshop fortune and he's Latin music's answer to Elvis. Would be interesting to know what these two had in common.
Image: Adriana M. Barraza/WENN.com
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Jesse James and Sandra Bullock
We all know how this marriage exploded and Bullock handled it with consummate dignity and class (because she's amazing) and James went on to go through a series of relationships with tattooed babes, some of whom, not surprisingly, claimed he cheated on them. Tsk. Tsk.
Image: A. Miller/WENN
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Rihanna and Chris Brown
This has to be the most cringe-worthy relationship in celeb hookup and breakup history. From the initial beating that rocked the world to a continued on-again, off-again affair a couple of years later, we're so glad Rih Rih has moved on. She's the toast of the fashion world, spinning off radio hit after hit with a voice that's all her own. He's...in jail. Not surprised. And not sorry.
Image: WENN
