18 Most Unlikely Celebrity Couples Of All Time

It’s a fact of life that celebs date other celebs (so yeah, your dreams of bagging Ryan Gosling probs won’t happen). But over the years there have been some truly weird pairings in Hollywood. These couples are sometimes so short lived we don’t hear about them until after they’re done, and sometimes they go on for way too long.
As bystanders, we have no idea how the dynamics in these relationships work but we can sure as hell look from the outside and comment on how friggin’ weird it is. Here are some of biggest celebrity odd-couples that make us look back and say “WTF?”!

18. Cher and Tom Cruise

As far as celeb couples you never knew about go, this one takes the cake. These two dated?! Not only did they date but Cher named Tom as one of her “top five” former lovers. So yeah, they were pretty close. It’s crazy to imagine these two together now but the ’80s were a weird time, kids. Tom and Katie Holmes were a much more fathomable couple.

17. Avril Lavigne and Brody Jenner

This super weird couple dated for TWO YEARS. Celeb-reality party boy (also Kylie Jenner‘s half-brother) Brody and “rocker” chick Avril were both at the height of their early-’00s fame when they got together and rocked worlds. She was def not a Lauren Conrad type (yanno, Brody’s other famous ex) making this pairing a little strange. Avril even had him wearing anarchist T’s and eschewing his preppy ways for a while. It just wasn’t meant to be, though, and after the couple split Brody was back to his party boy lifestyle.

16. Mila Kunis and Macaulay Culkin

Long before Mila was Mrs. Ashton Kutcher, she was in a long, serious relationship with former child star Macaulay Culkin. The two were actually together for many years (eight!) before eventually splitting. But still — weird. Mainly because Macaulay was at the height of his drugged out-looking, out-of-it phase and Mila is, well, totally chill and together. And a friggin’ babe. All’s right in the world now as she married Kutcher and Kelso and Jackie (i.e. their That ’70s Show counterparts) are finally together in real life.

15. Katy Perry and Russell Brand

These two may have seemed perfect together on the surface, but if you think about it long enough they were actually a very weird pairing. Russell is outlandish and kind of a huge jerk. Katy is sweet and way more sensitive than Russell could ever be. So it’s weird that she would MARRY this guy. Unfortunately, he proved what a jerk he was when he dumped her — you know, ending their marriage — via text. She moved on to much bigger (and hotter) things after that weird mistake. Hello, John Mayer and Orlando Bloom. Russell’s become completely irrelevant.

14. Mariah Carey and Nick Cannon

One of the most jarring Hollywood couples ever that yet we were all totally rooting for. The absolute QUEEN of pop (and Christmas) and… Nick Cannon? Nah. Too weird. Where did these two even meet?! It’s a strange pairing, perhaps because of their ten-year age difference and as we all know, it ended in divorce. They did make two adorable kids so it was well worth it. It also appears like their pretty great at co-parenting, which is a win in itself.

13. Kim Kardashian and Nick Cannon

You really can’t pin a type for Nick Cannon, can you? How does he keep getting women WAY out of his league?! (No offense.) Sure, it was the early aughts and Kim Kardashian wasn’t Kim Kardashian, leader of the Kardashian empire yet, but it’s a pretty odd pairing. Also, get this: Nick dumped her! Allegedly it was because she lied about her now-infamous sex tape. A world in which Nick Cannon can date, and then dump, Kim Kardashian once existed y’all.

12. Sandra Bullock and Ryan Gosling

Before he was everyone’s fave heartthrob, Ryan was just a young baby-faced actor dating a much older woman: Sandra Bullock. These two had a 16-year age difference during their romance, meaning she was learning to drive when he was being birthed. Just to put it in perspective. This predates his epic romance with Rachel McAdams (Allie and Noah 4EVA), and everything happens for a reason so who knows? Without the oddly matched Sandra/Ryan, we may have missed out on a truly iconic mid-aughts couple…

11. January Jones and Ashton Kutcher

Before they were famous for more than a few modeling campaigns, these two were an item. Considering the diverging paths their careers have taken, it’s strange to think that these two would even be on each other’s radars. Especially weird since Ashton didn’t support January’s acting career and thought she wouldn’t be good at it. Jokes on you dude, she’s got more talent in her pinky finger than you’ve had in anything ever. JK, Ashton’s fine, but that’s seriously not cool.

10. Demi Moore and Ashton Kutcher

Luckily Ashton is happy with his wife Mila Kunis now because he’s been in multiple strange couples in the past. His relationship — and eventual marriage — with Demi Moore was all kinds of weird. Demi having full-grown adult children closer in age to Ashton than she was should’ve been the first red flag but alas. He was still a young playboy when they met, and she was an established and settled actress. There was a lot of drama when their marriage eventually came crashing down, but the fact that they lasted as long as they did is kind of impressive.

9. Alanis Morissette and Ryan Reynolds

Did you know these two were engaged and actually almost got married?! Yeah, me either. These two were together for over four years when they split in 2007, predating Reynolds two high-profile marriages since. They seem odd because Ryan is such a jokester, and Alanis seems so… not. I mean, she does write angry songs for a living. Reynolds married Scarlett Johansson very soon after and that didn’t exactly work out for him, either. Good thing he’s got Blake Lively and a bunch of cute kids now!

8. Renee Zellweger and Bradley Cooper

Renee and Bradley earned a place on our list simply because he is known for his womanizing ways with many younger women and she’s actually six years his senior and doesn’t seem like she’d put up with his sh*t. But once upon a time, he was in a serious relationship, and even lived with the Bridget Jones star. Before his career really took off and he became the de facto Academy Awards best actor nominee, he was struggling to get by in comedy movies and bit parts. Reportedly he dumped Renee to further his career and, presumably, date lots of young models.

7. Evan Rachel Wood and Marilyn Manson

She was 19. He was 36. Oh, and he was still married. So, yeah, not the most normal relationship. She was young and rebellious and looking for freedom in an older, edgier guy — we get it. But it was totally not meant to be. They were in two different places in life. The shocking relationship ended a year after the two got engaged but, luckily, did not actually get married.

6. Chelsea Handler and 50 Cent

This short-lived couple was super random and short enough that the two weren’t ever actually photographed together. Though, she was seen going to one of his concerts. The two met when he visited her show and they hit it off from there. They had a fun little fling, but it seemed kind of out of nowhere. What could a late night comedian and rapper have in common? Apparently enough for them to gush about each other during and after their romance.

5. Michelle Rodriguez and Zac Efron

Admittedly, these two made up one of the hottest couples in recent memory. And while they say opposites attract, these two seemed way too opposite to even like each other. Michelle’s a wild child action star, and Efron is a teen heartthrob from The Disney Channel. They had a short, sexy fling and after two months that was that.

4. Taylor Swift and Tom Hiddleston

As Tay proclaims on her newest record, she loves toyin’ with them older guys. Her short-lived affair with Marvel megastar Hiddleston was so out of nowhere. Quickly after her romance with Calvin Harris ended, she was spotted making out with Hiddleston on the beach. It was weird, in part because the relatively private Taylor (aside from what she spills in her songs) was having a public free-for-all with this relationship. It just seemed… fake. (They both claim it wasn’t.) As quick as it started, it was over and Taylor went into relative hiding, eventually finding her new love Joe Alwyn.

3. Courtney Stodden and Doug Hutchinson

Oh boy, the pantheon of weird Hollywood couples. These two are as wrong for each other as can be. It doesn’t get much weirder than them getting married with she was 16 and he was 51. It’s a totally creepy romance that almost surpasses weird right into downright disgusting. The two split (for the second time) earlier this year, but seem to be living together still for the time being. Hopefully, they can both move on to some more normal relationships.

2. Jennifer Lawrence and Darren Aronofsky

Hollywood it-girl Jennifer Lawrence could have any guy she wants and she chooses… Darren Aronofsky? The controversial director is almost twenty years her senior and also known for being kind of a weirdo. The two met while filming mother! last year, a film that in and of itself is weird as hell, too. They broke up last month when Darren reportedly couldn’t stop talking about the film and obsessing over reviews. Jennifer’s young and has her whole future ahead of her, she definitely doesn’t need to be settling with some old man. No offense!

1. Jenny Slate and Chris Evans

These two may be an odd-couple but they’re also one of the most AMAZING Hollywood couples ever, in our HUMBLE opinions. He’s an action star known for playing Captain America, she’s a comedian known for going all out in her sometimes-bizarre characters. We would never have thought to pair these two together but now that they’re a thing, we’re celebrating the weirdness so hard. While half the haters think he’s too good for her, the other half of the haters think she’s too good for him. That should mean their pretty well-balanced, no? Seriously, this unlikely pair is all kinds of cute and has us wishing for more strange pairings to crop up in Hollywood.

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