The 10 Most Heartbreaking Celebrity Splits Of All Time

In the wake of what may have been one of the most shocking and much buzzed about splits in recent history (T. Swift and Calvin, of course), we got to thinking about the many times in the past we’ve watched our most beloved celebrity couples part ways, sometimes amicably while at other times, not so much. In the end, most—if not all—have found love anew, but we can’t help but feel nostalgic for the salad days of these lost loves. Here, 10 of the most heartbreaking celebrity splits of all time.

Getty Images

Brad Pitt and Jennifer Aniston

We know that everyone in this scenario is happier now than they were then, but it somehow doesn't really matter—we're still so sad about this split. At the time of their marriage, Jen was sort of positioned in the press as an "everywoman" (because of her role as the lovable Rachel in Friends and despite being rich and famous), and seeing her snag the hottest guy in Hollywood gave us all hope.

Getty Images

Heidi Klum and Seal

Heidi and Seal were together from 2005 to 2012, and they officially divorced in 2014. We thought they were going to last forever given their decision to publicly renew their vows every year they were married, but Seal apparently wasn't very fond of the ritual. We definitely miss them as a couple, but we're mostly just glad Heidi didn't scrap her epic annual Halloween party when she and its co-host separated.

Getty Images

Ryan Gosling and Rachel McAdams

We're totally cool with Ryan and Eva as a couple, but nothing will ever compare to Ryan and Rachel. We blame The Notebook for our committed obsession to these two—"If you're a bird, I'm a bird." Sigh.

Getty Images

Jennifer Garner and Ben Affleck

We're not going to say much about Jen and Ben because the wounds are still fresh and the rumors are still swirling, but all we can say is that we would be happy to see these two work things out (for non financial reasons).

Getty Images

Johnny Depp and Vanessa Paradis

We loved the understated nature of this longtime couple, but at least they gave us Lily-Rose before they split.

Getty Images

Britney Spears and Justin Timberlake

Justin and Jessica (Biel) are one of our favorite couples, but that doesn't mean we're totally over early aughts Britney and Justin. Remember when he allegedly wrote "Cry Me A River" as a Britney burn? We do, and we'll never forget.

Getty Images

Amy Poehler and Will Arnett

We loved these two so much we may just have to pretend they never broke up. Denial is healthy, right? #Poenett4Ever

Getty Images

Ashton Kutcher and Demi Moore

Ashton and Mila are an adorable couple, and we're happy they found their way back to each other (and are now on to baby #2). Still, watching Demi unapologetically love someone nearly half her age, in the way only men are normally allowed to do, was at least some small step towards changing the way women are perceived after their twenties.