Valentine’s Day is nearing and what a better way to spend the Hallmark holiday than by looking back at our favourite failed relationships? But we’re not talking about our own personal relationships, oh no that’s way too real, and frankly, there’s not enough vodka in the world for that. Instead, we’ve rounded up the celebrity couples who, when they called it quits, had us screaming, “if these beautiful, rich, and famous people can’t make it work, what chance do the rest of us trash people have?” Here are some of the breakups that nearly broke us.
Brad Pitt & Jennifer Aniston
A breakup so painful (for us) that in this, the year of our Lord 2020, a full 15 YEARS after they announced their split, we are STILL stanning hard for these two to reunite. Their recent interaction backstage at the Screen Actors Guild Awards last month has been studied more closely and with more attention to detail than the Zapruder film. For seven years, Brad and Jen were the ultimate It Couple, appearing effortlessly cool and in love and often in coordinating outfits and hairstyles (as Brad Pitt is known to do with his romantic partners) Their 2005 breakup, and Brad’s subsequent relationship, with his Mr. and Mrs. Smith co-star Angelina Jolie, sent shockwaves through the world, it tore families apart, turned friends into enemies, and divided a nation with people passionately declaring they were firmly on Team Aniston or Team Jolie. When Brad and Angie eventually broke up in 2016 followed by Jennifer Aniston splitting from her second husband, Justin Theroux, a year later in 2017, our minds immediately filled with visions of Brad and Jen texting each other late at night like, “You up?” Only time will tell if these exes find their way back to each other, but for now they appear to be merely friends. Nobody told us life was gonna be this way.
Ryan Gosling & Rachel McAdams
This one really shook us and honestly, it still hurts to talk about, but we’ll power through. Ryan and Rachel hold an extra special space in our hearts because, not only were they just so lovely together, not only are they both Canadian (even born in the same hospital in London, Ontario!) and not only was 2004’s The Notebook the pitch perfect cinematic love story, but they also gave us one of the most epic pop culture moments when, in 2005, after winning Best Kiss at the MTV Movie Awards, they walked up to the stage, took separate sides, and with Maroon 5’s “She Will Be Loved” playing in the background, ran toward each other, and with Rachel’s legs wrapped around Ryan, the real-life couple passionately kissed in front the entire crowd. If Twitter had existed at the time, it would have exploded just like our hearts did. Even Lindsay Lohan in the audience could be seen exclaiming, “Oh My God!” and you know she’s seen some shit. While both Ryan and Rachel have gone on to find happiness with new partners, in our hearts, “It still isn’t over!” (Except that it’s 100% totally over)
Tom Cruise & Nicole Kidman
Okay, looking back with the benefit of hindsight, we’re no longer sad Tom Cruise and Nicole Kidman broke up. In fact, Tom’s 2005 couch-jumping episode on Oprah, his weird relationship with Katie Holmes, his even weirder relationship with Scientology, his bizarre and terse exchange with Matt Lauer (although now we don’t know who to root for in that smug-off) has us thankful to Xenu that Nicole got far and away from Tom. But back then, in 2001 when it was announced that the days of thunder were over for the royal couple of the red carpet, our eyes were wide shut, and we were devastated. How could this have happened? Was it something we did? But while our hearts have since healed and Nicole has moved on with current husband Keith Urban, one lingering question remains: where the hell is Shelly Miscavige? Seriously, does anyone actually know?
Jennifer Lopez and Ben Affleck
Aaaah Bennifer. Without Jennifer Lopez and Ben Affleck, there would have been no TomKat, no Brangelina, and there definitely wouldn’t be Kimye, because Ben and Jen (version 1.0, that is) were the very first celebrity couple portmanteau and for that we are eternally grateful/resentful. Bennifer burned bright for two years before eventually crashing and burning harder than Gigli did at the box office. But from 2002 – 2004 they were everywhere and it was impossible to escape them. There they were on the red carpets, Ben Affleck with his slick hair and spray tan, on magazine covers (Ben was named People‘s Sexiest Man Alive during the height of Bennifermania) NBC even devoted an entire Dateline episode to interviewing them (imagine, a Dateline episode minus murder?) and of course, we will never forget no matter how long we live, no matter how much I’m sure they wish we would, the absolute time capsule that is Ben’s cameo in J-Lo’s video for “Jenny From the Block.”
Channing Tatum & Jenna Dewan
We’re not above being superficial every once in a while, so we’ll say, without shame, that whenever a super attractive couple breaks up, we’re maybe a little bit more down and out than we would be if say, a regular-looking couple breaks up. #NotSorry. We hoped Channing and Jenna, with their chiseled abs and flawless moves would step up and make it all the way till death did them part but alas, in April of 2018, the couple announced they would no longer be partners on the dance floor, or in life. The news gut punched us and while we’re never gonna dance again because, as a wise man once said, guilty feet ain’t got no rhythm, we will always have the memory of Channing and Jenna on “Lip Sync Battle” where she absolutely nailed her impression of his Magic Mike character whilst bumping and grinding to Ginuwine’s “Pony.” Channing and Jenna may be over, but our saddles are still waiting.
Gwyneth Paltrow & Chris Martin
It was back in 2014 when Gwyneth Paltrow and Chris Martin announced, “with hearts full of sadness” (on her Goop website, naturally) that they would be “consciously uncoupling” news that was met with a mix of mockery and melancholy. The rock star and the Oscar-winner married in 2003 and, despite being high-profile celebrities, managed to keep the majority of their private life private. But we still though of them as couple goals because they seemed to have it all. Chris Martin even wrote the Coldplay smash hit, “Fix You” for Gwyneth after her beloved father passed away. Little did we know how prophetic the lyric, “when you try your best, but you don’t succeed” would be because sadly, their marriage could not be fixed. The split came as more of a shock than their decision to name their daughter Apple. Gwyneth truly does everything with grace and perfection, including getting divorced, because this breakup has gone down as one of the most amicable in Hollywood history. Not only are the exes still friendly, they hang out, and even vacation with their current partners, Gwyneth’s husband producer Brad Falchuk and Chris Martin’s girlfriend, actress Dakota Johnson.
Ryan Phillipe & Reese Witherspoon
These two exuded major prom queen and king vibes when they went from reel-life couple to real-life couple after co-starring in 1999’s Cruel Intentions. Even though they both aren’t Gemini vegetarians, they got married and welcomed their daughter Ava that same year, while Reese was still just in her early 20s and on the precipice of major stardom. So honestly, we didn’t have a whole lot of hope they’d survive for very long in the Hollywood hype machine. But they proved us wrong, for a while anyway, and welcome their second child, son Deacon in 2003. But it wasn’t long after Reese won an Oscar in 2006, that she and Ryan walked the line into a divorce lawyer’s office. Reese is now happily remarried to talent agent Jim Toth and is busy producing every single piece of content you’ve consumed over the past three years. As for Ryan, well we could Google to find out what he’s up to, but we’ve already stopped caring.
Britney Spears and Justin Timberlake
They were our sun they were our earth, but they didn’t know all the ways we loved them. Okay, these two were super young when they got together so this was not built to last, even without the insane levels of fame and notoriety they gained over the course of their relationship, but that didn’t stop us from hoping this teenaged dream would have a happy ending. But alas, that was not to be. And while Justin didn’t have to say what Britney did because she already knew, he did give us a pretty good hint about what went down through his song “Cry Me A River” and its corresponding, and shady as hell, music video featuring a Britney lookalike. The damage was done and I guess he was leaving. And while we’ll truly never know what could have been for this former Disney duo, they did at least gift us with their truly iconic denim on denim on demin extravaganza at the 2001 American Music Awards and for that we are forever indebted to them.