Brit + Co Logo

Brad Pitt used to date who?!

8 Surprising Red Carpet Couples We Totally Forgot About

red carpet couples
Pascal Le Segretain/Getty Images

When any red carpet rolls around, there are certain couples we can pretty much always count on to show up looking cuter than ever. John Krasinski and Emily Blunt, Eddie Redmayne and his wife Hannah Bagshawe, Chrissy Teigen and John Legend… But anyone who’s ever seen a tabloid knows that celebrity couples often have a relatively short lifespan. And so when we decided to look back at the red carpet couples of the past, we rediscovered a whole bunch of duos we totally forgot ever existed. These stars are incredible on their own, but even more powerful together. Scroll on down to take a look at all the now-Hollywood exes who made us do a double take.


Juliette Lewis + Brad Pitt

Juliette Lewis + Brad Pitt

Vinnie Zuffante/Archive Photos/Getty Images

We tend to think of Angelina and Jennifer as Brad’s two big loves, but before them (and Gwyneth) came Juliette Lewis. The two dated for four years when they were both on the cusp of total stardom. These two just might be tied with Johnny Depp and Kate Moss as the most ’90s couple that’s ever existed.

Michael Jackson + Brooke Shields

Michael Jackson + Brooke Shields

Michael Ochs Archive/Getty Images

A budding supermodel and a global pop sensation? It’s kind of a Hollywood match made in heaven, just like Brooke's curls. That dress on the other hand? We’re not so sure.

Matthew Broderick + Jennifer Grey

Matthew Broderick + Jennifer Grey

Vinnie Zuffante/TriStar/Getty Images

As much as we’d like to believe Sarah Jessica Parker was Matthew Broderick’s one and only, this couple makes a lot of sense. The two were both the main characters in epic teen ’80s movies – we’ll just forget about the fact that they played brother and sister in one of them…

Jake Gylenhaal + Reese Witherspoon

Jake Gylenhall + Reese Witherspoon

Pascal Le Segretain/Getty Images

Dang, why didn’t this couple work out again? Oh right, probably because that much wonderfulness packed into one couple would make the world explode. But they sure did look good together!

Drew Barrymore + Corey Feldman

Drew Barrymore + Corey Feldman

Vinnie Zuffante/Getty Images

Feldman once said that his first date with Drew was arranged by her mother when she was 10 and he was 14, because apparently Barrymore had a huge crush on him. They later dated briefly (this time for real) in 1989, when Drew was a teenager. Unfortunately, he was heavily into drugs during that time and she was trying to stay sober after multiple stints in rehab, so it didn’t last long.

Winona Ryder + Christian Slater

Winona Ryder + Christian Slater

New World Pictures/Getty Images

Here’s to hoping this relationship ended a little more amicably than it did for their Heathers characters.

Julia Roberts + Kiefer Sutherland

Julia Roberts + Kiefer Sutherland

Vinnie Zuffante/Getty Images

It was supposed to be one of the biggest Hollywood weddings ever, and then all of a sudden, Julia called it off. Tragic. At least we have this red carpet moment to remember the couple by.

Stacy Keibler + George Clooney

Stacy Keibler + George Clooney

Jason Merritt/Getty Images

Now that Amal is in the picture, it’s hard to imagine George with anyone else. But before that British vision of elegance came Stacy Keibler, the stunning professional wrestler and George’s beau for two years.

Who’s your favorite throwback red carpet couple? Share with us on Twitter @BritandCo.

This post has been updated.

Selfmade

Selfmade

A business accelerator for early-stage female founders with live workshops, 1:1 mentoring, online courses, and curated business support. Visit

Yap City

Yap City

Want the inside scoop on what’s really trending? Join insider hosts Chloe Williams and Kayla Walden each week as they dissect their latest TV & movie obsessions, must-read books, and OMG moments you won’t believe. Visit