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The Strangest Celebrity Couples

September 29th, 2013 12:07pm EDT

Carmen Electra and Simon Cowell Love is blind, or so they say. Even in Hollywood, where image is everything, we've seen our share of odd pairs. Here are some of our favorite Strange Celebrity Couples, past and present.
Simon Cowell and Carmen Electra
A blinked-and-you-missed-it romance, these two dodged dating rumors after meeting on the set of Britain's Got Talent - but it was never confirmed they actually hooked up. However, those rumors came back with a vengeance thanks to Simon's scandal with Lauren Silverman - some reports even claimed the two of were broken up when she learned he was cheating on her with Silverman.

Mary-Kate Olsen and Olivier Sarkozy
Ever since Olsen left the acting biz, she's been keeping low key and designing fashion. However, she made headlines last year when she appeared at a basketball game with Olivier Sarkozy, 17 years her senior. They certainly appear to be happy together, and earlier this year it was rumored the two are engaged, although they are keeping everything quiet.

Demi Moore and Ashton Kutcher
The butt of many jokes, Kutcher dated and married Moore even though she was 15 years older than him. The two wed after two years of dating and kept it going for 7 years before divorcing.

Macaulay Culkin and Mila Kunis
Culkin was largely out of public view by the time he and Kunis starting dating in 2002. That may have been part of the allure, as Kunis definitely values her privacy. After nine years together and multiple rumors of marriage (Kunis said several times she "Wasn't about marriage"), the two finally broke up.

Hayden Panettiere and Wladimir Klitschko
The petite Panettiere wowed fans when she stepped out with hulking Russian boxer Klitschko. The couple, separated by 15 years and over a foot in height, has been on-and-off for a few years. However, at the moment they are back together and creating rumors a wedding could be on the way.

Amber Tamblyn and David Cross
These two took their time, dating for over four years before getting engaged. Cross, who is 19 years older than Tamblyn, admits, "I was slow to make any moves because of our age difference, and also because she was a fan." The two were engaged for a little over a year before tying the knot last year.

Juliette Lewis and Brad Pitt
Lewis and Pitt were two actors trying to make it big in the late 80s and early 90s. The two lived together for a time before breaking up - right before Lewis was in Cape Feare and Pitt was in Thelma & Louise. Lewis gets a little annoyed about questions on Pitt and told the Daily Mail in 2010, "There's nothing I can say or divulge about Brad Pitt that would be remotely interesting to any intelligent being."

Madonna and Vanilla Ice
Madonna has had a few odd boyfriends - in fact, they could make up their own article. However, we have to give the nod to Van Winkle, who appeared with a fully nude Madonna in her explicit "Sex" book. Van Winkle said he broke up with Madonna over it after seeing the way the photos were used.

Billy Corgan and Tila Tequila
Billy and Tila enjoyed a romance that was shorter than her popularity.

Moby and Natalie Portman
In 2001, between episodes 1 and 2 of the new Star Wars trilogy, Moby and Portman dated for a while. Thanks to Natalie's involvement in the venerable sci-fi series, Moby received what he calls "a lot of nerd wrath."

Amanda Bynes and Seth MacFarlane
Back in 2008, before her numerous troubles, Bynes and MacFarlane dated despite their age difference of 12 years. They broke up just as quietly as they dated - Bynes wasn't making headlines for her behavior yet and MacFarlane wasn't hosting the Oscars, so it wasn't exactly newsworthy.

Russell Brand and Katy Perry
It seemed like a joke when it was reported Brand and Perry were dating, but then it got all-too real when they pulled off their lavish wedding in India. In Perry's biopic/concert film Part of Me, the two are shown having a fight over having children (Brand was ready, Perry wasn't). It's believed that was the main reason Russell filed for divorced.

Related: Amanda Bynes, Amber Tamblyn, Ashton Kutcher, Billy Corgan, Brad Pitt, Carmen Electra, David Cross, Demi Moore, Hayden Panettiere, Juliette Lewis, Katy Perry, Macaulay Culkin, Madonna, Mary-Kate Olsen, Mila Kunis, Moby, Natalie Portman, Russell Brand, Seth MacFarlane, Simon Cowell, Tila Tequila, Vanilla Ice, Wladimir Klitschko, Celebrity, Relationships, WENN Photos, Evergreen

Photo Credits: PR Photos, WENN, PacificCoastNews

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