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Let’s face it, breakups are never easy. There’s crying, and a bunch of unwanted emotions, and you basically live off of cookie dough and sad movies until you’re ready to start the healing process. You could have the most amicable split known to mankind, and it can still hurt too much to get out of bed. No one likes having a broken heart, but it’s especially tough when the breakup is on the messier side. Could you imagine not only having a messy breakup but it be on magazine covers everywhere? It’s a true nightmare that, sadly, many celebrities have gone through.
With celebrity breakups, there are a few different types: the one where you know an intense breakup album is coming, one where they release a joint statement and amicably co-parent, and one where all hell breaks loose.
When we’re talking about messy breakups, we’re talking about the really dramatic kind. The ones where there are social media fights, subtweets, lawsuits, and even dumping over Twitter (we all know that one!)
So if you’re in the mood to walk down memory lane and remember when these relationships were all over the news, you’ve come to the right place. Check out which celebrity couples had the most dramatic and messy breakups ever, below:
Kevin Costner & Christine Baumgartner
Since Christine Baumgartner first filed for divorce from her Yellowstone actor husband in May, 2023 after almost 18 years of marriage, the former couple have been locked in a heated legal battle over child support payments for their three children. The legal back-and-forth has been nothing short of ruthless with conflicting accusations coming from either side. We’ll have to check back in to see if this breakup is ever finalized.
Tom Sandoval & Ariana Madix
Ah yes, Scandoval: the insanely messy breakup drama surrounding Vanderpump Rules‘ Tom Sandoval and Ariana Madix. Throughout the end of 2022, Sandoval and their co-star Raquel Leviss underwent an affair, with him later reportedly ending his relationship with Madix on Valentine’s Day.
During the show’s finale, which aired on May 17, the two confronted each other and it got messy really fast. “I regret every moment that I stood up for you, defended you, supported you. You’re worth nothing and I want you to feel that deep in your soul,” Madix told her ex. At another point, Sandoval asked if she wanted anything else from him, to which Madix responded, “For you to die.” Rough.
Kim Kardashian & Kanye West
Kim Kardashian filed for divorce in Feb 2021 and Kanye West did not take the breakup well. Not only did he post threatening messages on social media towards her and her beau at the time Pete Davidson, but he made many public jabs that made her fear for her safety.
Kristen Stewart & Robert Pattinson
Back in the late 2000s and early 2010s, Robert Pattinson and Kristen Stewart were the moody “It” couple, and everyone wanted to know more about the former Twilight star’s love affair. All seemed to be picture perfect, until the summer of 2012. In case you forgot, Stewart was seen making out with her married Snow White And The Huntsman director Rupert Sanders.
Once the photos were released by Us Weekly, Stewart issued an apology saying, “I’m deeply sorry for the hurt and embarrassment I’ve caused to those close to me and everyone this has affected. This momentary indiscretion has jeopardized the most important thing in my life, the person I love and respect the most, Rob. I love him, I love him, I’m so sorry.”
They got back together, but within less than a year, they called it quits for good. Per Us Weekly, Pattinson reportedly couldn’t trust her and once he skipped a birthday party she threw for him, it all went to hell.
Joe Jonas & Taylor Swift
Swifties know this one well: the incredibly messy breakup between then-teen idols Taylor Swift and Joe Jonas. Back in 2008, she revealed that he dumped her in a 27-second phone call after four months together. So in her teenage angst, she retaliated by making a Myspace video mocking him with a Camp Rock doll. (And of course writing scathing songs about the romance like “Forever & Always,” “Last Kiss,” and “Better Than Revenge,” per Cheat Sheet!)
Calvin Harris & Rita Ora
Calvin Harris and Rita Ora’s relationship was a rocky one, to say the least. Now, some people breakup over text, but Harris did it by tweet: “To address speculation — myself and Rita ended our relationship some time ago. She is a beautiful, talented woman & I wish her all the best.” Ora later revealed she learned about their breakup from that tweet. Ouch.
Iggy Azalea & Nick Young
Iggy Azalea and Nick Young not only called off their engagement multiple times, but it was evident that Young cheated on her multiple times. There was both video footage, and later Nick’s ex Keonna Green was four months pregnant with his kig when he and Azalea split.
Sandra Bullock & Jesse James
Jesse James publicly admitted that he started cheating on her just weeks after tying the knot to Sandra Bullock in 2005. They divorced in 2010, soon after all the news broke about his infidelity. Not only that, but after they split, and when he got together with Kat Von D, he said she was “100 percent” better in bed than Bullock, per UsMagazine.
Miley Cyrus & Liam Hemsworth
After a long on-again-off-again relationship, Miley Cyrus and Liam Hemsworth tied the knot on Dec 2018. However, less than a year later, they announced their split and Cyrus quickly moved on with MTV reality star Kaitlynn Carter. Per InTouch, “Liam hit the roof when photos emerged of Kait and Miley hooking up. It was the straw that broke the camel’s back.” So he filed for divorce.
However, it was alleged that Hemsworth cheated on Cyrus throughout their relationship, and she later wrote the song “Flowers,” which many believe is a dig at Hemsworth.
Christie Brinkley & Peter Cook
Christie Brinkley and Peter Cook got married in 1996 and were together for 12 years until explosive details came out about Cook’s affair. For those that don’t know, Cook had an affair with his 19-year-old assistant Diana Bianchi, and Bianchi later did a tell-all interview about the affair, saying:
Avril Lavigne & Mod Sun
Besides Scandoval being one of the biggest dating scandals in 2023, another big one was when Avril Lavigne called off her engagement to Mod Sun and then started dating his buddy Tyga only a week later.
Olivia Wilde & Jason Sudeikis
If your eyes were glued to Twitter in 2022, then chances are you know all the drama between Olivia Wilde and Jason Sudeikis. So Sudeikis and Wilde were in a relationship for nine years, first getting together in Nov 2011. They got engaged less than two years later in 2013, welcoming two children named Otis and Daisy. However, they announced their separation, and soon after, she and Harry Styles made their relationship public.
Along with their long, arduous custody battle, there have been claims from their former nanny, cheating allegations (with that salad dressing fiasco), and serving court papers at press conferences.
Kelsea Ballerini & Morgan Evans
So Kelsea Ballerini and Morgan Evans met as co-hosts of Australia’s Country Music Channel Awards in 2016 and got married soon after. Nearly five years later, they announced their shocking divorce, and a lot of heartbreaking details came out from Ballerini about how she didn’t really want to get married. Then breakup songs, depressing social media updates, and a new relationship from Ballerini happened within six months of the divorce news.
Jennifer Aniston & Brad Pitt
Jennifer Aniston and Brad Pitt’s breakup may be one of the most well-known, since it started a decades-long debate. For those that don’t know, the world basically shattered when their marriage fell apart after five years. The reason? It was reportedly because of Pitt’s affair with his second wife Angelina Jolie.
Demi Moore & Ashton Kutcher
After eight years of marriage, Demi Moore and Ashton Kutcher called it quits because of Kutcher’s alleged cheating. The rumors have followed him for years, and Moore even wrote about it in her memoir Inside Out. She also wrote about how he tried to angle for threesomes, something she didn’t want to do. She wrote, “I put him first. So when he expressed his fantasy of bringing a third person into our bed, I didn’t say no. I wanted to show him how great and fun I could be. There was two different people we opened our relationship to, and they didn’t have bad intentions … They were good people, but it was still a mistake.”
In response, he tweeted: “I was about to push the button on a really snarky tweet. Then I saw my son, daughter, and wife and I deleted it. ❤️”
Khloe Kardashian & Tristan Thompson
Khloe Kardashian and Tristan Thompson dated on and off again for around five years, from 2016 to 2021. They welcomed their daughter True in April 2018. They separated for good in 2021, with word breaking out soon after that Thompson had cheated on Kardashian and welcomed a child with a woman named Maralee Nichols.
Then the two shocked the world when they announced in July 2022 they were expecting a baby boy via surrogacy, and they welcomed him into the world within the same month. Since then, they have worked to co-parent their two children, and even made a joint appearance for True’s birthday.
Rumors of reconciliation have been in and out of the media, but it’s safe to say these two are over.
Adrienne Bailon & Rob Kardashian
Adrienne Bailon and Rob Kardashian dated for two years, and looked as happy as can be from 2007 to 2009. However, Kardashian admitted to cheating on her during an episode of Keeping Up with the Kardashians. Per Life and Style Mag, he claimed he “was cheating and having sex with so many different people.”
Gwen Stefani & Gavin Rossdale
Gwen Stefani and Gavin Rossdale were married for 20 years before it all came crashing down. Per Us Weekly, Stefani found out Rossdale cheated when the nanny found intimate photos and texts on the family’s iPad of him and another nanny.
Tom Cruise & Katie Holmes
After nearly six years of marriage, Katie Holmes filed for divorce in 2012 from Tom Cruise — and everyone had so many questions. Holmes allegedly filed due to fear of Cruise abducting their child Suri into the Church of Scientology, and since then, she’s reportedly solely taken care of their daughter.
Tiger Woods & Elin Nordegren
Who could forget when Tiger Woods and Elin Nordegren broke up? This breakup covered every news outlet, with new details coming out about Woods’ multiple affairs, sex addiction, and embarrassing text messages.
Angelina Jolie & Brad Pitt
So not only did Angelina Jolie and Brad Pitt have a rocky start with those cheating allegations, but their breakup in 2019 was somehow even messier than Pitt’s breakup with Aniston. After their divorce has come a multi-year battle consisting of custody battles, abuse allegations, and that infamous property battle over their winery.
Pamela Anderson & Tommy Lee
Pamela Anderson and Tommy Lee’s relationship was as turbulent as can be. After Lee’s jealous bouts, an incident happened that pushed on their first breakup. Anderson and Lee broke it off after a terrifying incident where Lee ended up being arrested for spousal abuse in 1998. Anderson said she was holding 7-week-old Dylan in her arms while Brandon played nearby. She was watching both of them when Lee walked up to her and said, “‘I want my wife back.’” She told him to “grow up” and give her “some f***ing help around here … It’s not about you anymore.”
She filed for divorce the next day to “protect her babies,” and the divorce was finalized a year later.
However, the two rekindled their romance in 2008 and split again in 2010 for the final time.
Megan Fox & Machine Gun Kelly
In early 2023, Megan Fox posted a cryptic Instagram post of a Lemonade lyric, later unfollowing Machine Gun Kelly and deleting posts of them together. Many rumors swirled about his infidelity until Fox had to put it to rest, and as of April 2023, they seem to be back on. But only time will tell.
Amber Heard & Johnny Depp
Everyone knows about Amber Heard and Johnny Depp’s tumultuous relationship, but here’s a recap: Heard filed for divorce in May 2016 after a year together and immediately filed a restraining order. She alleged that Depp had verbally and physically abused her. She wrote an op-ed and leaked a cell phone video in which a visibly intoxicated Depp could be seen shouting and throwing wine glasses.
After this, their highly-publicized court hearing occurred. In 2020, Depp accused Heard of assault, which she tried to counter-sue. Then on April 11, 2022, Depp’s defamation trial against Heard began, and a few months later, Depp won the trial.
Shakira & Gerard Pique
Shakira and Gerard Piqué were together for over a decade after meeting in 2010 on the set of her music video “Waka Waka.” Then in 2023, cheating allegations came out, and Shakira later wrote the hit song “BZRP Music Session #53” that shaded Pique. Since then, Shakira allegedly did petty moves toward his mother, and has since moved out of the country with their children.
Denise Richards & Charlie Sheen
Denise Richards and Charlie Sheen’s relationship was a scary one, to say the least. Their breakup happened in 2005, when a pregnant Richards filed for divorce from Sheen due to his drug abuse, had serious anger management issues, and gambling addict. After a bitter custody battle, Richards got a restraining order against Sheen. All seemed calm until Sheen tweeting things about Ricards, saying she was “worst mom alive” and “an evil terrorist.”