Celebrity relationships are a lot like McDonald’s french fries; they’re amazing when they’re fresh, but after a little while, they grow cold and lose all of their flavor. Since the majority of celebrities only date other celebrities, and most first dates in Hollywood end in marriage, it stands to reason that every celebrity has been married to another celebrity at least once. Is that math correct? I wonder. Either way, everyone knows that celebrities are against having strong and meaningful relationships. That’s why there have only been like three celebrity couples that have lasted throughout the years. I guess when you’re constantly playing other people, you see firsthand the allure of another life. Or maybe the cost-restrictive marital system just doesn’t scare these rich people away. They can date, marry and divorce all with a month’s paycheck.
With all that free love going around in Hollywood, there are bound to have been some strange couples over the years. It is a lot to keep track of, especially if you’re into that sort of thing. Or, if you’re anything like me, you’ve probably stopped caring about who’s dating who a long time ago. It’s hard enough to keep up with who T-Swift is with each week; keeping on top of all celebrity couples is just impossible. Well, you can still not care, but let’s at least look back and recap some of what you missed along the way. There have been some really strange couples and really hush hush couples. We’re not talking about quick flings, or as normal people call them, one-night stands. We’re looking at weird couples who actually presented themselves as a couple. Basically all of these pairs have since split, but that’s just part of what makes them so amazing. Here are 15 stars you never knew were a couple.
15. Rashida Jones and Tobey Maguire
Tobey Maguire, before he got that Spider-Man money, always appeared to be around in Hollywood but never a big name. He’s been a thing since he was a kid, and Leonardo DiCaprio dragged him around places as well. Well, during this age before his huge fame, Maguire was dating the gorgeous Rashida Jones. Jones wouldn’t become a household name for several more years after this point, but Maguire was on the verge of breaking out. The two were together for almost three years before they split in 2000. Both would move on shortly afterwards and get engaged to other people, but you have to wonder if Maguire is regretting letting Jones go nowadays. Not only has her career blossomed, but she is still insanely good looking, and that’s the most important thing.
14. Gary Oldman and Uma Thurman
While shooting the film State of Grace, in 1989/90, young stars Uma Thurman and Gary Oldman met and hit it off. Oldman was coming out of his first marriage, which he broke off shortly after the birth of his child, and Thurman was really just starting her career. The two would marry in 1990 and stay together for two years. During this time, it’s said that Oldman struggled with alcohol, even getting arrested for driving under the influence in ’91. Oldman has always been incredibly private about his personal life, so little is known about the relationship other than that. It’s too bad they didn’t stay together though. They seem like a cool pair.
13. David Arquette and Drew Barrymore
In 1991, 20-year old David Arquette and 16-year old Drew Barrymore, when they were both considered a little bit wild, had a relationship that they made public. The stars dated for some time, but broke it off to see other people. Some years later, the two would be reunited to play their respective roles in the 1996 film, Scream. Though they didn’t really have much time together since Barrymore was killed off so quickly, it must have been a bit weird for the ex-lovers because that’s also where Arquette met his future wife and ex-wife, Courteney Cox. Later, in 1999, Arquette and Barrymore were asked to play brother and sister in Never Been Kissed, which must have been even weirder for the pair. These days, when asked about their relationship, the two only have nice things to say about each other, so it sounds like they had fun in their time together.
12. Isla Fisher and Sacha Baron Cohen
In 2002, Isla Fisher and Sacha Baron Cohen met and they’ve been together ever since. Actually, in all the couples on this list, these two are the only ones still together today. So why did they make it on here? Really it’s because everyone always forgets these two are together, and, by everyone, I mean me. I always forget these two are together. They’ve been married now for six years, together for 14 years but, for some reason, they seem like an unlikely pairing. Perhaps it’s because Baron Cohen is such a silly person that it’s hard to imagine him taking anything serious, let alone relationship, but here they are, nonetheless. This Hollywood wonder couple also has three children. Let’s see if they can withstand the relationship-breaking machine that is Hollywood for 14 more years.
11. Ryan Reynolds and Alanis Morissette
Way back in 2002, fellow Canadians Ryan Reynolds and Alanis Morissette, started their love affair. The couple lasted for two years and then decided they should get engaged. This engagement lasted for three long years but then ended in 2007. Shortly after their engagement split, Morissette wrote a few songs about Reynolds, while Reynolds went out and started dating Scarlett Johansson. We all have our individual coping mechanisms. Some choose creating art, like music, and others chose works of art like Scarlett Johansson. One year later, Reynolds and Johansson were engaged to be married, but this couple actually went through with it… for a short period of time at least. Two years later, the two split. Never change Hollywood.
10. David Spade and Julie Bowen
Say what you will about David Spade, the guy has done quite well on the acting scene. He’s made boatloads of money and hasn’t been all that funny in years. There was a time when he was considered one of the kings of comedy. These days, critics would sooner punch their own faces than give him a positive review. In terms of relationships though, he’s had a number of beautiful women at his side, including the always lovely Heather Locklear, but the time he spent with Julie Bowen is maybe the strangest of all. Back in 2002, before she was better known as Claire Dunphy from Modern Family, Bowen met Spade and somehow the little guy wooed her. They dated for about a year before Dunphy left and got married and had kids to another man. Spade, always the lover of Playboy models, got together with playmate Jillian Grace and had a daughter with her.
9. Drew Barrymore and Corey Feldman
In 1989, two years before she was with David Arquette, teen star Drew Barrymore was dating teen star Corey Feldman. Feldman (18) and Barrymore (14) had recently done a TV special together and were thought to have started dating then, but Feldman suggests it started quite a bit before that. He said that their relationship actually started when Barrymore was 10 and Feldman was 14, which is hilarious. No one dates when they’re 10, do they? Do they? Both of these young actors struggled with addiction during their teen years, so it begs the question. Were they good for each other or not? At the 1989 Academy Awards, the two young’uns showed up together arm in arm and flaunted their love to all the old jaded movie stars. Barrymore could have been on this list a few times as she tended to jump between actor boyfriends every year or so. Despite her breaking all these hearts, it seems that every one of her exes are still crazy about her.
8. Tom Cruise and Cher
When Tom Cruise was 25 years old, he apparently had a love affair with the, then, 41-year old rocker, Cher. Cher has been very vocal about this weird relationship, like a last-ditch effort to cling to her glory days. She says that Cruise ranks highly in the list of men she’s had in her life. Cruise on the other hand doesn’t mention much at all. The fling was brief but, if you ask Cher, it was “hot and heavy.” She says that they were crazy for each other, but seeing as how quickly Cruise moved on from Cher after their break and how little he says about it today, it is likely that it was more one-sided than the singer was led to believe. Plus, Cher has been in her own world for so many years now that she’s probably lost touch with reality. That being said, it’s doubtful that Tommy boy has ever been in touch with reality being the strange little alien-like creature he is. Regardless of what happened, this couple had a whole lot of weird in it and it really gives this list an extra something.
7. Cameron Diaz and Jared Leto
Cameron Diaz has dated quite a few big stars in her time in Hollywood. Since she stepped on the screen, she’s been seen as one of the most beautiful movie stars in the world. She’s been with Matt Dillon, Alex Rodriguez, Justin Timberlake and finally, hubby Benji Madden, but amidst these little bouts of love, Diaz was also with Jared Leto. For some reason, even though the two were together for four years and even engaged to be married (which seems to be a trend for celebrities), Leto tends to be the forgotten one of Diaz’s past partners. For some reason, these two just don’t seem to match. Diaz seems ditzy and aloof and Leto is heady and a bit odd. Maybe it’s true what they say, opposites attract, or maybe we just don’t really know these stars like we pretend we do. It’s probably the first one.
6. Colin Farrell and Elizabeth Taylor
To say that they dated may be a bit of a stretch, but if you asked Colin Farrell, he’d like to have thought they were. In 2009, while at the hospital for the birth of his second son, Farrell bumped into one of Taylor‘s people and that chance encounter led to a relationship of sorts until Taylor’s death in 2011. Now, if you’re thinking, that dog! He’s out there laying the groundwork for a relationship with another woman while his son is being born. Well, yeah, that’s exactly what he was doing. He and the child’s mother, Ondine co-star, Alicja Bachleda-Curuś, would split not too long after that hospital date and Farrell (33) and Taylor (78) kept on trucking until she passed away. There’s an entire lifetime of years between those two, but that didn’t stop them.
5. Jason Schwartzman and Zooey Deschanel
Right before Zooey Deschanel worked on Almost Famous, and later New Girl, she was dating the well-known actor Jason Schwartzman. When the two stars started dating (both 19-years old at the time), they were said to be just having fun but, as their careers started to take off, they drifted apart. A couple of years later, so the story goes, Dustin Hoffman invited both of them over to his house, knowing about their history. When he left the two of them alone intentionally, it was obvious to the two actors that Hoffman was trying to set them up.
4. Liv Tyler and Joaquin Phoenix
In their late teens and early 20s, Liv Tyler and Joaquin Phoenix had a pretty serious relationship going. Tyler says that Phoenix was her first love. How sweet. The two have remained good friends through the years, long after their breakup. Phoenix has nothing but nice things to say about Tyler (which is a common thread with all of her exes). “What can I say?” he said, “we hit it off immediately. She’s a darling. I’ve said it over and over again. She’s just very real, right there, never like a movie star. She’s so genuine, and she doesn’t take herself too seriously. It shows in the work she does that her honesty stands out most.” Tyler seems like the nicest person on the face of the Earth, so it’s entirely believable that they would stay friends through the years.
3. Liam Neeson and Helen Mirren
In the 80s, the two megastars Liam Neeson and Helen Mirren, met and fell in love, and it was magical… probably. It was on the set of Neeson’s first film, Excalibur, where the two met. Neeson said in an interview, “I fell in love with Helen Mirren. Oh, my God. Can you imagine riding horses in shiny suits of armor, having sword fights and stuff, and you’re falling in love with Helen Mirren? It doesn’t get any better than that.” Mirren, seven years older than Neeson, took Neeson under her wing like a baby duck and helped him out in his early days in Hollywood. He credits her as an incredible influence for him in that time. The two lived together for some years in the 80s before finally calling it quits and going their separate ways. There obviously remains a great amount of respect between the two, which makes sense considering how beautiful these two legends are.
2. Ryan Gosling and Sandra Bullock
After meeting on the set of Murder by Numbers, then 22-year old Ryan Gosling and 38-year old Sandra Bullock, felt that they should get together and give love a chance. The two dated for about a year and even went public with their relationship, but Gosling left her for greener pastures; greener being less experienced… at life. You know the saying. Not long after the breakup, Bullock got together with and married Jesse James, not the gunfighter, and the rest is history. Now Gosling is with Eva Mendes in a very quiet and handsome relationship.
1. Winona Ryder and Matt Damon
In 1997, in between dating other megastars, the 80s sensation Winona Ryder was introduced to an up-and-coming actor named Matt Damon. Damon had just made Good Will Hunting and would soon become a major name in Hollywood. Gwyneth Paltrow, who was at the time dating Damon’s best pal, Ben Affleck, introduced the two and it was love at first sight, well, at least that’s how we’ve imagined it. They stayed together until 2000 when Damon left her and moved on to Penelope Cruz and then to someone else. Ryder and Damon have remained on speaking terms since the breakup, which is nice.