Love Hurts! The Messiest Celebrity Breakups Ever — Brad and Angelina, Kim and Kanye and More

Jennifer Aniston and Brad Pitt

These two were the “it” couple after tying the knot in 2000. People just couldn’t deal when their marriage fell apart after five years because of the actor‘s reported tryst with his Mr. and Mrs. Smith costar Angelina Jolie. He attended a birthday celebration in his ex’s honor in February 2019, which raised a whole lot of eyebrows. However, it was revealed after their unexpected reunion that they “definitely aren’t dating or on that path.”

Angelina Jolie and Brad Pitt

A messy beginning led to a messy ending. The two actors announced their split in 2016 and have been battling it out in the courtroom ever since. They share six kids — Maddox, Pax, Zahara, Shiloh and twins Vivienne and Knox.

Ashton Kutcher and Demi Moore

Before he was Mila Kunis‘ dream man, Ashton Kutcher had a bumpy love life. He and Demi Moore split after eight years of marriage in 2013 amid tabloids capturing the actor allegedly cheating. “I’m also probably the first person to get this award for character who had, like, his name splashed across every gossip magazine as an adulterer like five years ago,” he said on stage while accepting an award for good character in 2017.

Demi has since written a tell-all book called Inside Out where she documented more of their tumultuous relationship.

Ben Affleck and Jennifer Garner

Their divorce was finalized in October of 2018, but the two still had a three-year-long breakup that included reports of the actor cheating with their nanny back in 2015. They share three kids — Violet, Seraphina and Samuel.

Amber Heard and Johnny Depp

One of the ugliest divorces … ever. This couple’s split has been sadly filled with abuse allegations, threats of blackmail and tales of their relationship toxicity. “Johnny and Amber had one of the most twisted marriages you could ever imagine,” a source told In Touch at the time. “No one is going to come out of this divorce unscathed.”

Iggy Azalea and Nick Young

The basketball player and rapper broke off their engagement after multiple pieces of evidence surfaced that the athlete was cheating on her. To make things even more awkward, Nick’s ex Keonna Green — whom he already shared one child with — was four months pregnant with his daughter when he and Iggy split.

Kim Kardashian and Kris Humphries

This entire relationship is still a puzzler. The pair were famously married for just 72 days before divorcing in 2011. If that wasn’t bad enough, the basketball player accused the reality starlet of using him for fame and cheating on him with Kanye West — two things the KKW founder has denied. Their split wasn’t finalized until 2013, just days before she gave birth to her oldest child North West.

Kristen Stewart and Robert Pattinson

Our dreams came true when these Twilight costars were an item, but things crashed and burned quickly when photos of the actress kissing the franchise director, Rupert Sanders, surfaced. The exes briefly reconciled but quickly ended things for good in 2014.

Madonna and Sean Penn

Our ’80s dream couple broke our hearts when the split in 1989 after four years of marriage. Although there were accusations about violence erupting between the two, they kept a united front to the public. “I felt that no one wanted us to be together,” Madonna told Rolling Stone at the time. “They celebrated our union, and then they wanted us to be apart. There were rumors about us getting a divorce a week after the wedding. We fought that. And, yes, that is difficult. I don’t know if anyone can do it [under those circumstances].”

Rob Kardashian and Basically Everyone

The KUWTK star has had a rocky love life. First, in 2009, he and Adrienne Bailon broke up after he admitted to cheating on her during an episode of the famed reality show. Then, he went on a Twitter rant in 2014 claiming that Rita Ora cheated on him with “nearly 20 dudes.”

From revenge porn to child support lawsuits, it’s been nothing but drama with the mother of his child, Blac Chyna. Rob and Chyna, who share daughter Dream Kardashian, got together in 2016 but split for good one year later.

Sandra Bullock and Jesse James

Ugh, why? Our hearts broke for the Hollywood sweetheart when Jesse publicly admitted that he started cheating on her just weeks after tying the knot. More and more women started surfacing who claimed they slept with him during his five-year marriage to the actress. When he moved on with Kat Von D, he said she was “100 percent” better in bed than Sandra.

Selena Gomez and Justin Bieber

The teen heartthrobs’ breakup is especially awkward because they just can’t seem to quit each other. They dated on and off from 2010 to 2015 and were even seen hanging out before he got engaged to his now-wife, Hailey Baldwin.

Selena dropped two songs — “Lose You to Love Me” and “Look At Her Now” — at the end of October 2019 that fans think are about her tumultuous relationship with the pop star.

Taylor Swift and Calvin Harris

This was one of Taylor Swift‘s very last public relationships before Joe Alwyn. She and Calvin Harris were all loved up on social media and then shockingly broke up. When the songstress then started dating Tom Hiddleston (we want to believe this was real), the DJ did not hide his hurt feelings. He went on a Twitter rant calling out the songstress’ pseudonym, Nils Sjoberg, on his track “This Is What You Came For.”

He wrote in one tweet, “I know you’re off tour and you need someone new to try and bury like Katy [Perry] ETC but I’m not that guy, sorry. I won’t allow it. Please focus on the positive aspects of YOUR life because you’ve earned a great one. God bless everyone have a beautiful day.” The music producer also reportedly wrote the song “Ole” about their breakup.

Tiger Woods and Elin Nordegren

Tiger Woods was once a low-key athlete until his dirty laundry was publicly aired. His marriage to Elin Nordegren ended with reports of multiple affairs, sex addiction and embarrassing text messages being leaked.

Tom Cruise and Katie Holmes

When these A-listers announced their split in 2012 after six years of marriages, it was surprising to fans because nothing seemed amiss. Some people assumed it had something to do with Katie Holmes‘ disapproval of Scientology but they’ve kept the reasoning behind their divorce hush-hush.

Miley Cyrus and Liam Hemsworth

After the longtime couple announced their split in August 2019, things got a bit, er, messy … to say the least. Miley quickly moved on with MTV reality star Kaitlynn Carter while Liam was left heartbroken. “Liam hit the roof when photos emerged of Kait and Miley hooking up,” a source exclusively told In Touch at the time. “It was the straw that broke the camel’s back.”

Since then, Liam officially filed for divorce and Miley and Kaitlyn split. The pop star moved on with fellow singer-songwriter Cody Simpson, but the pair split in August 2020.

Tom Cruise and Nicole Kidman

Possibly no one in the history of the world has looked more jubilant than Nicole after finalizing her divorce from Tom, to whom she was married from 1990 to 2001.  

Nicole is currently happily married to Keith Urban. 

Gwen Stefani and Gavin Rossdale

The No Doubt singer and lead singer of Bush were married for 20 years and had three children when it was rumored Gavin was having an affair with the nanny. The couple split in 2015. According to Us Weekly, Stefani found out Rossdale cheated when a different nanny found intimate photos and texts on the family’s iPad.

Kristin Cavallari and Jay Cutler

Jay filed for divorce in April 2020, but the pair’s split quickly turned ugly when Kristen accused the former football player of “inappropriate marital conduct” and sought primary physical custody of their three children. 

Jennifer Lopez and Alex Rodriguez

Shortly after breaking off her engagement to the retired baseball player, Jennifer found herself back in the arms of Ben Affleck, 17 years after they called off their engagement. The reunited pair packed on the PDA around the world and look like they were planning for the long haul.

“A-Rod can’t take a hint,” an insider told In Touch. “She gets that she and Alex were together for five years, that they planned to marry and everyone was rooting for them, but it ended. It’s over. It’s done.” 

“[J. Lo] wants him to move on,” the source continued. “She wishes him well.”

Kim Kardashian and Kanye West

Kim filed for divorce in February 2021 after almost seven years of marriage. Kanye has not taken the breakup well, posting threatening messages on social media and making public jabs at her now-boyfriend, Pete Davidson.