Ranked: The 15 Saddest Breakups of 2016

No one got through this year unscathed—but 2016 was especially rough for famous couples. We take a look at the most brutal celebrity breakups

celeb breakups


Sofia Richie and Justin Bieber
It was a month-long thing that maybe wasn’t even actually a thing. We’ll be fine.
Sadness ranking:  🙁 

Chloe Moretz and Brooklyn Beckham
This pair was hella chill about their relationship—they confirmed it, but they didn’t share any details—which is probably why we can’t get too worked up about the split.
Sadness ranking:  🙁

Taylor Swift and Tom Hiddleston
Swifties were divided between shipping and ditching this unlikely duo. We’ll never forget the I <3 T.S. tank, but we’re not going to shed many tears over the end of Hiddleswift.
Sadness ranking:  🙁

Taylor Swift and Calvin Harris
This split hurt a bit more, but that might just be because Tayvin gave us 485 days without the mention of a new T.Swift boy toy. Here’s hoping 2017 brings Tay a little luck in the love department.
Sadness ranking:  🙁  🙁

Mariah Carey and James Packer
Mariah’s split from the Australian financier turned into a mysterious mess involving an unreturned engagement ring, a former Scientology spokesman and a $50-million “inconvenience fee.” We want butterflies and romance for Mariah, but we also live for her low-key shade, so we’re torn about this one.
Sadness ranking:  🙁  🙁

celeb breakups

Frances Bean Cobain and Isaiah Silva
After two years of marriage, our celeb-spawn fashion muse and her rocker husband, Isaiah Silva, signed the papers and dusted their hands of this relationship. Then things got nasty—like, the kind of nasty where Silva won’t give back the vintage guitar that Kurt Cobain played on MTV Unplugged. Dude, no.
Sadness ranking:  🙁  🙁

Demi Lovato and Wilmer Valderrama
Pop-singer extraordinaire Lovato and Fez were together for nearly six years before breaking their breakup news on Demi’s Instagram. We have to give them mad props for avoiding tabloid drama, despite their much-talked-about 12-year age difference.
Sadness ranking:  🙁  🙁  🙁

Naomi Watts and Liev Schrieber
After 11 years and two super-cute kids together, this couple called it quits, which seemed to catch everyone by surprise. But they’ve shown each other some birthday love on Instagram since the split, so maybe there’s still hope??
Sadness ranking:  🙁  🙁  🙁

Ozzy Osbourne and Sharon Osbourne
Give these crazy kids credit for making it 34 years together—through a lot of hard stuff (drugs, breakdowns) and weird stuff (that thing with the bat).
Sadness ranking:  🙁  🙁  🙁

Rihanna and Drake
Of all of Drizzy’s crushes, we really wanted him to make it work with our beloved Riri: The two had style for daaaaayyys. Fingers crossed that these two keep up their PDA-filled stage act. We’ll just be over here, mourning the name possibilities that could have been. (Drihanna… BadGalRizzy… AubRih….)
Sadness ranking:  🙁  🙁  🙁

celeb breakups

Diane Kruger and Joshua Jackson
Uggghhhh they just looked so good together. We’ve been hearing rumours about trouble between these two for ages, but the end of their 10-year relationship still hurts.
Sadness ranking:  🙁 🙁 🙁 🙁

Cara Delevinge and St. Vincent
After a year of romantic bliss, Cara and St. Vincent seemed like the perf couple—attending fashion shows, taking all the cute strolls—so we were totally caught off guard by this split. Then St. Vincent (aka Annie Clark) was spotted with fellow badass Kristen Stewart in October, but then she and Cara went to an L.A. museum together in December, so maybe they’re getting back together?
Sadness ranking:  🙁  🙁  🙁  🙁

Bella Hadid and The Weeknd
This one cut deep. Fans longed for Bella and Abel to reconcile on the VS Runway and make the world right again—but she blew past him, so no such luck. Sigh.
Sadness ranking:  🙁  🙁  🙁  🙁

Lady Gaga and Taylor Kinney
When news broke of Gaga’s breakup from beau Taylor Kinney, we refused to believe it. Then we ugly-cried all the way through “Million Reasons” and swore we’d never love a celeb couple again. At least there’s a lot of 2008-era Gaga badassery that can help us through the pain.
Sadness ranking:  🙁  🙁  🙁  🙁

Angelina Jolie and Brad Pitt
Our eyes will never dry for Brangelina. Twelve years together, extensive charity work, a soccer team of children and total smoking-hotness—this was THE saddest breakup of 2016, and the allegations against Brad made everything sadder still.
Sadness ranking:  🙁  🙁  🙁  🙁  🙁

We’re So Over Drake: Our Breakup Letter to Drizzy
Brangelina: An Epic Romance and Sudden Split, By The Numbers
Diane Kruger and Joshua Jackson Breakup: Fail or Not?