The 10 Oddest Real-Life Hollywood Couples Ever

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Hollywood can be a big, weird, lonely place. Sometimes, for better or worse, that's going to make you want to get with Cher. And as Woody Allen once said, in defending his controversial relationship with his adopted daughter, the heart wants what the heart wants.

It's not for us to judge.

Just kidding! Of course it is. Here are 10 of the most bizarre Hollywood couples ever, past and present.

Tom Cruise and Cher

Tom Cruise and Cher got together in the mid-1980s, and while we weren't there at the time or anything, it certainly feels like it was more of a "Hey, you're internationally famous? Crazy, I'm internationally famous too! Let's bone!" type of relationship than one based on love. Depressingly for all of us, somewhere in an alternate universe, their firstborn is debuting his/her/its bestselling tell-all book, "Cher-ry Maguire: My Life with Tom and Cher" right now on Dr. Phil.

Ted Danson and Whoopi Goldberg

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While married to his second wife in 1993, Danson had an affair with Whoopi Goldberg. Other than the whole "relationship based on infidelity" thing, their tryst seemed to be chugging along smoothly until Danson infamously showed up in blackface for a Friar's Comedy Club roast of Goldberg. In retrospect, it's hard to blame Danson, whom we imagine was merely trying to emulate the long list of instances where someone appeared in blackface and everyone thought it was both hilarious and in good taste, which we've gathered and listed below:


Lyle Lovett and Julia Roberts

26-year-old Julia Roberts was on top of the world in the early '90s, having just won universal acclaim for her role in "Pretty Woman" and ready to take on the new and exciting challenge of being a bona-fide Hollywood A-Lister. Step one? Shacking up with Lyle Lovett. After all, no lady can resist a man who plays a mean guitar, even if that man looks like a character from Gary Larson's "Far Side" cartoons. Sadly, Lovett and Roberts divorced only two years later, citing "irreconcilable faces."*

*Not a real reason to divorce someone.

Bradley Cooper and Renee Zellweger

This one might be a little unfair, but let's face it: Of the 3 billion men on Earth, Bradley Cooper was the sexiest of them all only two years ago, and Renee Zellweger has only ever won the 2005 title for Sexiest Woman Who Looks Like She Was Just Force-Fed An Entire Tree of Lemons. Both valid titles, but that doesn't make their partnership (which took place in 2010) any less bizarre.

Ashton Kutcher and Demi Moore

We all became kind of numb to this one after a little bit, but Ashton Kutcher and Demi Moore's sadly-doomed relationship was at least incredibly bizarre at its inception, considering Moore was a full-fledged Hollywood sex symbol around the same time that Kutcher was sprinting home from kindergarten in time to catch the latest episode of KIDS Incorporated. Alas, before (allegedly) doing the dirty dirty with another young lady, Kutcher failed to confiscate any and all camera phones.

Danny Boyle and Rosario Dawson

The only current relationship on this list has us tipping our caps to the "Slumdog Millionaire" director Boyle, who has managed to land one of the hottest women in Hollywood just by (we're guessing) being really good at directing movies. And so we have a very important lesson for all aspiring directors who can't quite work up the nerve to talk to the girl of their dreams: Don't bother trying, there's no way this would happen a second time if it's already happened once. Sorry.

Mila Kunis and Macaulay Culkin

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Most of the relationships on this list lasted for mere months before each party decided it was a bad idea; Kunis and Culkin dated for nine years! So while most of us were realizing exactly how scorching hot Mila Kunis might be (roughly around the "Forgetting Sarah Marshall" area), she had already been dating Culkin for six years. Good call, Kevin McCallister! Sadly, the two broke up in 2011 when Kunis realized she and Michael Jackson might be eskimo cousins.

Laura Dern and Ben Harper

A relationship that pretty much everyone was aware of yet no one really thought or talked about, Laura Dern and singer Ben Harper were married for five years before not-amicably divorcing in 2010. It's weird to think about Harper smoothly singing "Burn One Down" to 5,000 adoring fans before awkwardly saying into the microphone, "If you guys think 'Jurassic Park' is the best movie ever LET ME HEAR IT!"

Natalie Portman and Moby

"You don't date Luke Skywalker's mom and not have (nerds) hate your guts," said Moby of his brief relationship with Portman in what was unofficially measured as the biggest Humblebrag of all time. "(laughs) God all these nerds HATE that I boned Natalie, which I did do, by the way! Can't please everyone, I guess - but I did please Natalie! Sexually!" Got it, Moby. Take it easy. We believe you, even if there's no verification from Portman anywhere on the internet that this relationship actually happened. But those nerds must have hated you! LOL!

Angelina Jolie and Billy Bob Thornton

These two wore each other's blood in vials around their necks. It wasn't a result of a lost bet or anything, it was voluntary. And if anyone has seen the clip of Billy Bob telling MTV on the red carpet for the Movie Awards that the two "****ed in the car on the way here," they can tell you that you can't just block that memory out of your brain overnight, or even after years of intense therapy. It never goes away. The pair's split in 2003 would inadvertently serve as the catalyst for the end of Jennifer Aniston's life.