The 21 Weirdest Celebrity Couples Ever

Some celebrity couples make perfect sense… I mean, could you imagine a world without Bey and Jay or Will and Jada? Then there are the couples that seem so mismatched, we can’t imagine how they ever got together in the first place. Check out the strangest celebrity couples ever, and try not to scratch your head in confusion.
Zac Efron and Michelle Rodriguez
Zac Efron, Michelle Rodriguez
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These two surprised just about everyone when they stepped out together in the summer of 2014 looking pretty hot and heavy, but this ended up being not much more than a summer fling. Zac is now dating longtime girlfriend Sami Miro and Michelle has spoken up about enjoying keeping her personal life private. Still though, this was almost too much hotness to handle!
Jennifer Lawrence and Chris Martin
Jennifer Lawrence, Chris Martin
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After announcing he would be splitting from his wife Gwyneth Paltrow, tongues were wagging at rumors that he was taking up with J. Law, but the relationship fizzled as quickly as it begun. Bummer!
Macaulay Culkin and Mila Kunis
Macaulay Culkin, Mila Kunis
Few people seem to remember this pairing, but these two were in a serious relationship for eight years (!!). She went on to marry Ashton Kutcher, and he has been dating soap actress Jordan Lane Price since 2013.
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Tom Cruise and Cher
Tom Cruise, Cher
WENN/ via Splash News
Though they seem like an unlikely duo, the pop icon and A-list actor totally dated back in the mid-'80s, and Cher has had nothing but wonderful things to say about him since. She recently said in a TV interview that he was "in her top five" lovers. Yowza!
Moby and Natalie Portman
Moby, Natalie Portman
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The musician has long been subject to rumors about his sexuality, but he doesn't let it bother him. But after a brief romance with Natalie, Moby says "as far as the very brief affair I had with Natalie, it's made me the target of a lot of nerd wrath. You can't date Luke Skywalker's mom and not have them hate your guts." Yikes!
Brody Jenner and Avril Lavigne
Brody Jenner, Avril Lavigne
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After being linked to a string of blonde babes including Lauren Conrad, Nicole Richie, and Kristin Cavallari, it shouldn't seem so surprising he found love (for a while!) with the punk rock princess, but he did! They dated pretty seriously for about two years, even getting matching lightning bolt tattoos together! Sadly, she said "see ya later boi" to this sk8er boi, later marrying and then divorcing Chad Kroeger.
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Angelina Jolie and Billy Bob Thornton
Angelina Jolie, Billy Bob Thornton
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Before she was one half of the power couple known as Brangelina, Angelina Jolie was married twice: first to actor Jonny Lee Miller, and then to actor Billy Bob Thornton. This pairing mainly freaked people out because they wore vials of each other's blood as necklaces, and other TMI tidbits about their private lives. At the time, Angelina was known for her rebellious streak, so her marriage with Billy Bob was clouded by that, but they both remain great friends to this day. Aw!
Jennifer Love Hewitt and Jamie Kennedy
Jennifer Love Hewitt, Jamie Kennedy
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They costarred together on Ghost Whisperer and found love off-screen for a year, but Jamie admitted they were plagued by constant media attention and snarky headlines, which frustrated him. He revealed: "People weren't rooting for a good relationship. That was really hard to deal with. You see snarky headlines and eventually you just have to stop reading that stuff." Still, he has nothing but warm regards for his ex. Sweet!
Evan Rachel Wood and Marilyn Manson
Evan Rachel Wood, Marilyn Manson
This couple raised eyebrows at the beginning of their relationship because Evan was only 19 and Marilyn was still married to then-wife Dita von Teese, and they had a tumultuous affair for nearly four years. They were engaged in 2010, but split for good by year's end.
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Soon-Yi Previn and Woody Allen
Soon-Yi Previn, Woody Allen
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One of the most controversial Hollywood couples, this one gives creepy vibes due to the fact that Soon-Yi is the adopted daughter of Woody's then-partner Mia Farrow, and Mia allegedly found nude photos of Soon-Yi taken by Woody at the age of 21, and a nasty war of words between the exes commenced. For his part, Woody declined any wrongdoing and said he's never been a "father figure" to Soon-Yi, and they've gone on to marry and have two children, but there's definitely an inherent ickiness there.
January Jones and Josh Groban
January Jones, Josh Groban
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Admittedly, at the surface, this coupling seems totally random... but January and Josh dated for two and a half years, and Josh revealed to Details magazine after their split: "We dated for about two and a half years, and we were madly in love. It was definitely my longest relationship." Aw!
Ryan Reynolds and Alanis Morrisette
Ryan Reynolds, Alanis Morrisette
He's now half of one of Hollywood's cutest couples with Blake Lively, and she famously penned the revenge anthem of the century (that's "You Oughta Know," guys!) about Dave Coulier, but these two famous Canadians dated for five years and were engaged for three (!!) in the mid-00s. Who knew?!
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Kid Rock and Pamela Anderson
Kid Rock, Pamela Anderson
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Their flame burned white hot for a brief time, and Kid Rock became Pamela's second husband (she even donned a white bikini to their wedding. How romantic!) but it quickly sizzled and didn't end well, with Kid later saying: "I knew it was a bad career move to get involved with her because your life becomes a circus -- because that's what she wants is media attention." Yikes.
Cameron Diaz and Benji Madden
Cameron Diaz, Benji Madden
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She's known for being the goofy, girl-next-door actress and he for being a pop-punk king, but these two found love after being introduced by Benji's sister-in-law (and Cameron's good friend) Nicole Richie. They wed after a 17-day engagement after only seven months together, and seem to have found their happy ending. Crazy!
Mary-Kate Olsen and Olivier Sarkozy
Mary-Kate Olsen, Olivier Sarkozy
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Mary-Kate (along with twin sister Ashley) notoriously keeps her private life to herself, so eyebrows were definitely raised when she started seeing the much-older Olivier in 2012. The two seemed to be engaged in 2014, and tied the knot in 2015, so it looks like age really is nothing but a number for these lovebirds!
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Chelsea Handler and 50 Cent
Chelsea Handler, 50 Cent
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The sharp-tongued comedienne and the popular rapper don't appear on the surface to have much in common, but no one can deny their connection. After they split, 50 reportedly said: "Chelsea is confident. I think confidence is the sexiest thing about a person. She's the kind of person that if you're blessed with the opportunity to hang out with her, you'll enjoy it. I'm not sure you'll look at her and actually want to jump over the table and f*ck her, but you might. You would leave after talking with her feeling that she is a cool person." That's so sweet, I think?
Ashley Judd and Michael Bolton
Ashley Judd, Michael Bolton
Talk about totally random!  Michael and Ashley apparently had a brief courtship back in 1996. She even starred in his video for "The Best of Love," mullet and all! So sweet.
Ryan Gosling and Sandra Bullock
Ryan Gosling, Sandra Bullock
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They've both since moved on, but this gorgeous pair were in a serious relationship from 2002-2003 right before he hit peak fame thanks to his role in The Notebook. Seriously, who knew?!
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Carson Daly and Tara Reid
Carson Daly, Tara Reid
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Back when he was host of the wildly popular TRL and she was one of Hollywood's hottest young actresses, these two were super serious about each other. They were even engaged, but never made it down the aisle. Carson later said: "To some extent, I dodged a bullet. I was getting serious about my career, and she wanted to shoot movies and just party in her time off. That didn't work for me." He also said he was "done dating actresses," adding: "I realized I'd have more in common with a regular person than with a celebrity. There were values I was more likely to find in a nice, midwestern girl than one who was living on the coast, pursuing fame." Well, ouch!
Tom Cruise and Katie Holmes
Tom Cruise, Katie Holmes
Yeah, this one definitely takes the cake for weird pairings in Hollywood. We all know the story, Tom was Katie's childhood crush, fast-forward a few decades and he's jumping on Oprah's couch, declaring his love for her. They always made for an odd pairing, but seemed happy until... they weren't. Meep!
Jessica Simpson and John Mayer
Jessica Simpson, John Mayer
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After divorcing husband Nick Lachey in 2006, Jessica took up with the rock crooner for a yearlong relationship. She even dyed her hair dark and dressed a bit "edgier" during their romance, but it wasn't meant to be. He's since had a slew of high-profile romances, including Taylor Swift, Jennifer Aniston, and Katy Perry, and she went on to marry Eric Johnson.