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15 Of Hollywood’s Most WTF Celebrity Hookups

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15 Of Hollywood’s Most WTF Celebrity Hookups

All of us have that one friend that just keeps picking the strangest people to date. No matter who he or she brings to the party, you just can’t help but wonder how on earth these two met and furthermore – what in the name of all that is good and holy made them fall for each other?! Well, here’s some news for you, in case you hadn’t already suspected – celebrities are people, too. And just like us ordinary humans, they can get caught up in some really odd relationships that just leave you asking those very same questions.

In this list we’ve gathered some of the most shocking hookups in the world of fame and fortune that you simply couldn’t see coming. These will include stars that turn out to have met long before they rose to fame, and have known each other way better than you would have ever thought. Some of our picks will make you laugh with their absurdity, while others might even make you reconsider some of your relationship perceptions and notions of an ideal couple. Whatever the case, this list is sure to surprise you in more than just one way, so stick around and learn about some of the most baffling celebrity hookups in recent history.

15. Ryan Reynolds & Alanis Morrisette

via popsugar.com

via popsugar.com

Deadpool star and Hollywood hunk Ryan Reynolds had been spotted alongside quite a few famous beauties, before he met american actress Blake Lively, with whom he now shares three years of happy marriage and a lovely daughter. However, one particular relationship stands out quite a bit more than the rest – his 5-year commitment to ex-fiance and rock singer-songwriter Alanis Morrisette. The couple got engaged two years in the relationship, but they never actually made it to the altar, splitting up in 2007. Recently, Reynolds caused somewhat of a stir when he sang a line from Morrisette’s song ‘Ironic’, awkwardly bringing up his ex without even mentioning her name during an interview on The Today Show. Ironic, indeed.

14. Ashley Olsen & Jared Leto

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Well, to be perfectly honest, anyone who grew up watching movies starring the adorable little Olsen twins will be shocked to face the fact that they’re all grown up, and yes, dating. Put the knowledge of Jared Leto having a fling with one of them on top of that, and the shock just grows into confusion and downright stupefaction. Though she is no longer an actress, Ashley Olsen is still very much involved in the world of film, fashion and also with its men. A couple of years ago, Olsen had been spotted on multiple occasions together with actor and singer Jared Leto, who is 15 years her senior, by the way. We’d certainly be curious to find out what these two had in common.

13. Madonna & Vanilla Ice

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Wow. Not entirely sure whose perspective to view this from, but this one is sure to surprise absolutely everyone now (unless you already knew about it), perhaps more than it did in the distant year of 1991, when these two started dating. And it wasn’t a brief encounter either, the couple split up a year later after Madonna released her book titled Sex, in 1992. The book was the main reason for their breakup, as Robert Van Winkle aka Vanilla Ice shared later. According to him, the book featured some very indiscreet images of her and the rapper, as well as other men, which made him feel, “hurt to be an unwitting part of this slutty package,” and resulted in him initiating the split.

12. Christian Bale & Drew Barrymore

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Nowadays? Unthinkable. But who knew these lovebirds go a far way back, before they became the big names they are today. That being said, though, The Dark Knight star Christian Bale and actress Drew Barrymore maybe weren’t exactly the lovebirds you would think. Alright, they weren’t lovebirds at all. The two went out on a date once, back when they were teens and, apparently, the date didn’t go too smooth, because Barrymore never called Bale again. Years afterwards the latter recalled having gone to see “some bloody awful horror film” and with that the very brief love story had come to a sudden end. Barrymore’s explanation, when asked twenty years about the reasons for ‘dumping’ Christian Bale, was that she simply wasn’t that crazy for boys at the time. She had ‘bigger fish to fry’.

11. Zac Efron & Michelle Rodriguez

via celebuzz.com

via celebuzz.com

As far as unlikely couples go, this one scored pretty high in that category. Who would have thought that The Fast and the Furious star Michelle Rodgriguez would end up dating High School Musical cutie-pie Zac Efron? Especially since we’ve been so used to seeing the latter with co-star and former sweetheart Vanessa Hudgens… And the fact that they’ve always been the ultimate teenage pair. So how did Efron wind up with a woman 10 years his senior? We’ll probably never know, but what we do know is that the affair didn’t last long – two months, to be exact. Rodriguez and Efron were on vacation together and when the vacation was over, so was the romance.

10. Tupac & Madonna

via themdgestycollection.blogspot.com

via themadgestycollection.blogspot.bg

Yes, Madonna has made two lines on this list, because after her breakup with rapper Vanilla Ice, she moved on to date rap legend Tupac Shakur. This only became verbally confirmed by Madonna herself last year during an interview to Howard Stern. She said that she had dated the late rapper in 1994 and he had ‘riled her up on life’ at the time, making her ‘feel very gangster’. The relationship wasn’t a serious one and was never discussed in public, yet the singer regards the experience as having impacted her and she truly respected Tupac as a person.

9. Paris Hilton & Val Kilmer

via movies.film-cine.com

via movies.film-cine.com

Talk about random couples and here we’ve got one. Now, while it’s really no secret that Paris Hilton has ‘been around’, the socialite’s fling with actor Val Kilmer, who was nearly twice her age at the time, arouses many questions. The first one being, why? The actor has also been quite busy over the years, having dated many a pretty and renowned woman, such as Cher, Angelina Jolie and Cindy Crawford. In this case, however, the two met on the set of the movie Wonderland and the sensation of their brief encounter came to be thanks to some leaked pictures of Kilmer groping and kissing Paris Hilton.

8. Moby & Natalie Portman

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Bam! For reasons we’ll leave unnamed (they don’t deserve to be named), famous musician Moby has been mistakenly dubbed by many as gay. Though he supports the LGBT community and has spoken in favor of same-sex marriages, Moby himself is as straight as an arrow and has had quite a few high-profile relationships with women to prove it. His relationship with celebrated actress Natalie Portman, was relatively brief and took place back in 2001, but the two parted as friends and still have some things common, like veganism and social activism. Moby claims that his affair with Portman made him target to a lot of ‘nerd-wrath’ and explained this in an interview in the following words: “You can’t date Luke Skywalker’s mom and not have them hate your guts.”

7. Nicolas Cage & Angelina Jolie

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Now who would have even thought that anything prior to Brangelina ever existed? Well, it did. And it probably raised a few eyebrows along the way. This particular instance of ‘pre-Brangelina’ involved actor Nicolas Cage, who is some 11 years older than his Gone in 60 Seconds co-star Angelina Jolie. The two had been spotted kissing at a black tie event in 2003, which caused rumors of an alleged relationship to spread. No confirmations, however, followed, so whatever may have been going on between both celebrities – it didn’t last for long.

6. Sarah Jessica Parker & Michael J. Fox

via glamourmagazine.co.uk

via glamourmagazine.co.uk

There’s another unlikely hookup you wouldn’t have guessed in a million years. Sex and the City star Sarah Jessica Parker met Michel J. Fox on the set of Tim Burton‘s 1996 black comedy-science fiction film Mars Attacks. The two played a couple in the movie and rumor has it, their roles ended up spilling into real life.

5. Winona Ryder & Charlie Sheen

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There’s another shocker for you, in case you hadn’t known. And this romantic instance is another one of those that go so far back in time, that the fact of it is already baffling enough. Now, both Winona Ryder and Charlie Sheen have been around for quite some time and have had the pleasure of dating some of Hollywood’s most brilliant men and women. They even had the opportunity to date each other for a very short while. The two hooked up after meeting on the set of Ryder’s first ever movie Lucas, and some say that it was Sheen who convinced Winona to change her last name from Horowitz to Ryder, in order to have a better chance in Hollywood. Well, more points to Charlie Sheen, if this is true, as it seemed to have worked.

4. Colin Farrell & Elizabeth Taylor

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Here’s something you definitely don’t come across every day. Renowned womanizer, Hollywood’s ‘Lusty Leprechaun’, as he’s been labeled, and the man seen with so many famous and attractive women, was involved with a woman more than twice his own age! The two had been in a relationship for around two years, up until Elizabeth Taylor‘s death in 2011. Her and Colin Farrell were in fact so close that the latter was among the very few people invited to join the family in the private funeral. Farrell was deeply touched by Taylor and claims to adore her still, even after her passing. This couple’s affair was so intimate, Taylor actually hand-picked the poem for Colin Farrell to read at her funeral.

3. Taylor Swift & Calvin Harris

via popsugar.com

via popsugar.com

As you might guess, the reason this specific celebrity couple is on the list is because of Taylor Swift‘s well known relationship history and the anticipation of the messy break up that will likely follow. However, she is definitely trying to make the relationship with Calvin Harris (who has also had a number of broken hearts on his conscience, by the way) work. Swift has even gone as far as to fly back to him in between shows, while on tour. We should probably point out that the couple announced their relationship publicly shortly before Swift started touring, which might also have fueled her efforts.

2. Tom Cruise & Cher

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Another famous ‘cougar’ on this list is the one and only Cher. The diva has seen many a handsome lover, but among her top 5, as she disclosed during an interview only several years ago, is actor Tom Cruise. She mentioned that the two were dating for about a year, back in the mid 80’s, before Cruise had even dreamed of becoming a star yet. Cher also went on to say that the now famous actor was very different back then, looking at him now, she feels quite confused. The singer described him as being shy, but she also admitted to have been completely ‘crazy about him.’

1. Kristen Stewart & Soko

via popsugar.com

via popsugar.com

This is one probably nobody could have ever predicted. Kristen Stewart has always been a bit of a controversial persona and many have had trouble understanding her looks, her behavior and some life choices of hers even. Everyone heard of the little indiscretion she had with married director Rupert Sanders, which inevitably lead to her split with co-star and fiance Robert Pattinson. The scandal took its toll on her reputation and not much had been heard since, until she began dating French female singer SoKo. The irony here isn’t in the actresses’ decision to try dating someone of the same sex. In that regard, she had refused to label herself and define her sexuality. The irony is in the fact that SoKo had actually been set up on a blind date with Rob Pattinson prior to meeting Stewart. How’s that for a plot twist?

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