Weirdest Hookups In the History of Hollywood


Nothing excites fans quite as much as celebrity hookups. It doesn’t help that we spend most of our time cheering as celebs’ characters fall in love onscreen. The idea of hot celebs hooking up when the cameras stop rolling is that much more compelling!

There have been quite a few hookups in Hollywood history, and some are much weirder than others. But what are the weirdest hookups of all time? Keep reading to find out!

Robert Downey Jr. and Sarah Jessica Parker

Before he was known for Iron Man and she was known for Sex and the City, Robert Downey Jr. and Sarah Jessica Parker dated. Is it too late to hope for a modern, robot-filled MCU crossover titled Mechs in the City?

Bradley Cooper and Zoe Saldana

Technically, Bradley Cooper and Zoe Saldana have dated twice: once when they met filming The Words. Then, after they broke up, they hooked up again six months later. Sparks flew each time, but it wasn’t enough to kindle a lasting fire.

Cher and Tom Cruise

Cher didn’t have to “turn back time” when she hooked up with Tom Cruise at the beginning of his career. But since she was a full sixteen years older than the young actor, it’s fair to call this a bit of a May/December hookup.

Martha Stewart and Anthony Hopkins

The only thing funnier than the fact that Martha Stewart and Anthony Hopkins dated is the reason they broke up. And it’s exactly what you’re thinking: after Hopkins brought cannibal killer Hannibal Lechter to life in Silence of the Lambs, Stewart had to break up with him because she could never see him the same way again!

Daniel Day-Lewis and Julia Roberts

In the early ‘90s, Daniel Day-Lewis and Julia Roberts dated. At the time, the scuttlebutt was that longing for Day-Lewis caused Roberts to break up with Keifer Sutherland. No word, though, on whether Day-Lewis was method-acting during their time together.

Emily VanCamp and Chris Pratt

Some celebrity hookups are weirder than others. For example, Chris Pratt and Emily VanCamp became an item while they played siblings together on Everwood!

Matthew Perry and Julia Roberts

As Friends gained popularity, it helped the stars meet more Hollywood big names. And after Julia Roberts agreed to star in the show thanks to major convincing from Matthew Perry, the two ended up dating. However, he worried about heartbreak from this movie star big shot and ended up calling off the relationship.

Jared Leto and Cameron Diaz

In retrospect, it’s a tad weird that so few people remember Jared Leto and Cameron Diaz being an item. They dated for four years before going their separate ways. This helped Leto focus on the artistic skills needed to bring compelling characters like Morbius to life on the big screen.

Prince Harry and Catherine Ommanney

When it comes to Prince Harry and Hollywood hookups, we naturally think about his wife: American actress Meghan Markle. However, Real Housewives star Catherine Ommanney claimed she hooked up with Prince Harry back in 2006 after they met at Art Bar in London. Their relationship only lasted for a few dates before they called it quits.

Dax Shepard and Ashley Olsen

Dax Shepard somehow managed to never watch Full House. This was helpful when he met Ashley Olsen and they started going out. And as unconventional as their relationship was, they bonded over an unexpected share passion: cars!

Will Smith and Tyra Banks

Every now and then, reality is stranger than fiction. Will Smith and Tyra Banks were an onscreen item in The Fresh Prince of Bel-Air but also dated offscreen, too. This means you better not criticize her too loudly in Smith’s vicinity unless you want your face to have some “fresh prints” on them.

Ashton Kutcher and January Jones

January Jones is perhaps best known for kicking all kinds of ass on Mad Men. However, well before that show came on the air, she dated another legend of the small screen in the late 1990s: Ashton Kutcher.

Ryan Reynolds and Alanis Morrissette

Ryan Reynolds and Alanis Morrissette didn’t just date…they dated for a whopping five years! They called things quits after half a decade of dating in the early 2000s. We can only assume it was an amicable breakup because Morrisette didn’t shred Reynolds in a post-breakup song (looking at you, Dave Coulier).

Justin Timberlake and Fergie

Justin Timberlake and Jessica Biel have been an item for forever. But back when Timberlake was only sixteen, he hooked up with another future musical icon: Fergie. At the time, she was part of the musical group Wild Orchyd.

Michael Jackson and Madonna

In their own ways, Michael Jackson and Madonna are two of the most controversial musicians in history. At the height of their respective fame, these two hooked up. Sadly, though, this historic relationship was not meant to last.

Juliette Lewis and Johnny Depp

Few people have generated quite as much recent controversy as Johhny Depp, but he still has supporters. This includes Juliette Lewis, someone whom he briefly dated back in the early 1990s.

Jack White and Renée Zellweger

Renée Zellweger has dated many famous men, including legendary funnyman Jim Carrey. What most people forget, though, is that she dated musical superstar Jack White for a couple of years before they called it quits.

Salma Hayek and Edward Norton

Once upon a time, Salma Hayek and Edward Norton dated for three years. However, they broke up in the year 2000. Nothing quite like a new millennium to make people long for new beginnings!

Lenny Kravitz and Nicole Kidman

From 2003 to 2005, things were pretty serious between Lenny Kravitz and Nicole Kidman. These days, Kidman is happily married to Keith Urban, but things are cool between her and Kravitz. In fact, Kravitz and Urban even get along very well together.

Penélope Cruz and Tom Cruise

Again, sometimes the onscreen hookups serve as a preview of actual celebrity romance. Penélope Cruz and Tom Cruise met while filming the sexy mystery Vanilla Sky. And just as they hooked up onscreen, these two ended up having a steamy relationship that lasted three years.

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