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15 Biggest Celebrity Breakups Of All Time

Breakups are never easy. I’ve been through a lot since I was a teenager. My rule was to buy a cat every time my heart got broken, which is the reason why I have so many. They never disappoint me. Get a cat and never get your heart broken. Ever.

As a person who loves celebrity news and gossips, I always feel sorry for those poor Hollywood souls who have to endure the pain of a breakup in public. They may have the money to buy a pet after a breakup, but they don’t have the time to truly enjoy their love during a tough time. I now have an open-door policy for celebrities who need to cuddle with my cats when they’re sad.

These 15 celebrity breakups were some of the messiest and most talked about in the industry. We might never know the real reason, but somewhere out there is a fan that is happy because they finally have another chance to be with their idol.

Kris & Bruce Jenner

Kris-Bruce-JennerIf you think about it, Kris and Bruce Jenner’s relationship was completely random. Kris was an ex-flight attendant who used to be married to OJ Simpson’s lawyer. On the other hand, Bruce was an Olympic athlete that had his face on cereal boxes during his hey-days.

23 years of marriage and 9 seasons of a reality show later, Kris filed for divorce from her Olympic medalist husband. As fame-hungry as Kris is, her separation from Bruce was pretty clean and peaceful, unlike most Hollywood divorces. They both decided that they didn’t need spousal support from each other and stated that they kept their own stuff—with properties to be divided later on.

Maybe Bruce or should we say Caitlyn was a little too much woman Kris to handle…

Orlando Bloom & Miranda Kerr

Orlando-Bloom-Miranda-KerrOf course, who wouldn’t know who Orlando Bloom is? He’s a total hunk that has portrayed a lot of handsome heroes. He only made things better by marrying a supermodel, Miranda Kerr.

After six years of being together (3 of which they spent as husband and wife), Miranda and Orlando announced that they were separating. The holy union of a Victoria’s Secret Angel and Legolas came to a close after reports of Orlando turning into a different person when he gets drunk.

Orlando reportedly punched Justin Bieber, after the pop star made a move on Miranda. I guess that’s Orlando’s way of subliminally telling Miranda that he still has feelings for her, no? Well, I don’t see them reconciling anytime soon, as Miranda’s currently being linked to Tom Cruise—which might provide us with another Scientology-fueled separation in the future.

Miley Cyrus & Liam Hemsworth

Miley-Cyrus-Liam-HemsworthMiley Cyrus always makes my head hurt whenever she appears on TV or on the Internet. She baffles me! First off, Miley was with Liam Hemsworth for four years, and then admitted that they split up because she couldn’t be herself around him. That’s confusing and I think her parents need to guide her properly. Miley freaks my kitties out every single time they see her.

I don’t know if this is rebellion on Patrick Schwarzenegger’s part because of his parents, but he’s now Miley’s latest boy toy—something that his mother doesn’t agree with. As for Liam, there are rumors that he’s currently dating Hollywood’s sweetheart, Jennifer Lawrence.

Career-wise, Liam seems to be doing well because of his role in “The Hunger Games” series. I have no idea what’s going on in Miley’s career, but last I checked, she was riding a huge wrecking ball.

Heidi Klum & Seal

Heidi-Klum-SealThis breakup was something that I did not expect. Seal and Heidi Klum had four beautiful children and were so sweet with each other based on paparazzi photos. Heck, they even renewed their vows every year! However, after seven years of togetherness, they split up in January 2012.

They were such a cute couple, getting married every year and taking their kids out and about together. The supermodel and the singer were very rare, given that they weren’t afraid to show the world how happy they were.

Apparently, Seal has issues with his anger and accused Heidi of cheating on him with her bodyguard, Martin Kristen. Seal also made some comments about Heidi having no class. Even if Heidi did admit to her relationship with her bodyguard (which is her current boyfriend!), what Seal did was a little ungentlemanly.

Jesse James & Sandra Bullock

Jesse-James-Sandra-BullockWe all know Sandra Bullock as one of the most-recognizable faces in Hollywood because of her work in the movies. As for Jesse James, we all know him as the heavily tattooed guy from that random reality show.

Sandra is such a beautiful woman and a wonderful actress. I never did understand why Sandy chose to marry Jesse James in 2005, but I suppose she had her reasons. Five years later, boom! So many women came forward, admitting that they had an affair with Jesse James. One month after the scandal broke, Sandra filed for divorce and continued on being her talented self.

Jesse then proved that once a cheater, always a cheater, after his rebound, Kat Von D, publicly admitted that he cheated on her with 19 women. It really dislike this Jesse person, philandering around ruining the lives of women.

Halle Berry & Gabriel Aubry

Halle-Berry-Gabriel-AubryWell, looks like Halle Berry made a bad decision with this one! Halle is an actress that’s been in so many males fantasies because of her beauty and talent. Her ex-husband was also beautiful, considering that he was a model.

Halle Berry and Gabriel Aubry were so prominent in the tabloids during their relationship, that my cats are still shredding some magazines with their faces on them. They had a bitter custody battle over their daughter back in 2010 and never really agreed on anything. Halle attempted to bring her daughter Nahla to France, in order to avoid the paparazzi in the US. Gabriel brought the issue to court and won. Then, as a surprising climax, Gabriel and Olivier Martinez (Halle’s current husband) got into a fistfight during Thanksgiving in 2012 and both ended up in the hospital.

Charlie Sheen & Denise Richards

Charlie-Sheen-Denise-RichardsAside from being the man responsible for the hashtag, #Winning, Charlie Sheen is known for his movies in the 80’s. He met his second wife, Denise Richards, during the filming of his sitcom, “Spin City.” 3 years after their marriage, everything spiraled out of control.

Oh, Charlie. Why did you let go of the woman who stuck with you through and through? Things were going so haywire between Charlie Sheen and Denise Richards that Denise filed for divorce while she was pregnant with their second daughter. Apparently, Charlie was a porn addict who abused her and threatened to kill her. He called her out in public and said that Denise was, “a sad, jobless pig who is sad and talentless and sad and jobless and evil and a bad mom.” I ought to hit him with my walking stick just for saying that to the mother of his children!

Brad Pitt & Jennifer Aniston

Brad-Pitt-Jennifer-AnistonBrad Pitt and Jennifer Aniston used to be one of the most attractive husband and wife pairs in Hollywood. Brad was the hottest hunk on the planet, and Jen was the prettiest lead on the hit show, Friends.

It’s been a decade since they parted ways, but it was still surprising, nonetheless. Their relationship was considered to be successful in Hollywood, seeing that their marriage lasted for almost five years before they split. Then, rumors about Brad’s infidelity surfaced. During their split, he didn’t address the rumor that much and let the paparazzi photos speak for themselves. However, he has went on to admit that he had fallen in love with Angelina Jolie during the filming of “Mr. and Mrs. Smith.”

Brad now shares six kids with Angelina, and Jen is now married to Justin Theroux, whom she dated since 2011. Now, I just want to see something on the news about how Jen and Angelina are friends now.

Rihanna & Chris Brown

Rihanna-Chris-BrownWhile I was growing up, my daddy always told me that boys shouldn’t hit girls even if they’re asking for it. I think Chris Brown didn’t get the memo about not resorting to violence when it comes to girls.

Back in 2009, a photo of Rihanna’s battered face surfaced. Chris Brown had beaten her up inside a rented Lamborghini. The police were involved, then the media, which turned Chris Brown into one of the most hated men on the planet. Since then, they’ve been on and off, but it seems like Rihanna has finally moved on. This time, with Leonardo DiCaprio, if the tabloids are correct.

Arnold Schwarzenegger & Maria Shriver

Arnold-Schwarzenegger-Maria-ShriverCalifornia’s former governor and first lady seemed to have a solid relationship prior to their separation. Tom Brokaw introduced Arnold Schwarzenegger and Maria Shriver to each other in 1977, and the couple got married in 1986. After 25 years together, it was revealed that the Austrian bodybuilder hadn’t been faithful to the former Kennedy.

This relationship is a great example of why you should have a solid prenuptial agreement before tying yourself down. A few days after Maria Shriver filed for divorce in 2011, a former night maid in the Schwarzenegger household came forward in the media about how she had an affair with the governor that resulted in a son.

As of December 2014, I haven’t read any confirmations of Maria’s and Arnold’s divorce being finalized—mainly because they haven’t agreed on how to split the $400 million fortune they earned during their marriage.

Ashton Kutcher & Demi Moore

Ashton-Kutcher-Demi-MooreThis couple was both beautiful in their own rights—Demi Moore was one of the hottest stars from the 80’s, starring in films like “St. Elmo’s Fire” and “Ghost.” On the other hand, Ashton Kutcher was a model who got famous after starring in “That 70s Show.”

When Demi married Ashton in 2005, she gave older women like me a reason to not be afraid of getting out there. If it weren’t for the cats, I would’ve pulled a Demi and gotten myself a younger man too. Anyways—six years later, a divorce plea for their marriage was filed. It took two years before it got finalized, as the former couple weren’t seeing eye to eye when it came to the financial aspect of their split.

Just recently, Ashton welcomed a baby daughter named Wyatt with fiancé, Mila Kunis. As for Demi? Her most recent boyfriend was a 27-year old drummer named Sean Friday.

Princess Diana & Prince Charles

Princess-Diana-Prince-CharlesOf course, what would this list be if it weren’t for the most royal couple that divorced right in front of the public’s eyes?

I was in awe when these two got married in 1981. They’re not exactly Hollywood, but they are very well known all over the world. Even if they were together for 11 years, their union was imperfect. Prince Charles cheated on Princess Diana from the start with his current wife, Camilla Parker-Bowles. The monarchy didn’t allow him to marry Camilla, as she had already been married before. Diana was handpicked to become his wife, a recipe for disaster from the beginning.

It took years before their divorced was finalized in 1996. Diana received a rumored $32 million and had her title, “Her Royal Highness” removed. A year later, she died immediately after suffering fatal injuries from a car crash in Paris.

Reese Witherspoon & Ryan Philippe

Reese-Witherspoon-Ryan-PhilippeReese Witherspoon and Ryan Philippe were the cutest, kitty version of Hollywood couples in the 00’s. The pair met while at a party thrown for Reese’s 21st birthday—where they spent the whole night talking to each other. They were engaged to each other by the time they starred in “Cruel Intentions” in 1999.

They married young and were blessed with two children. But after 7 years, they pulled the plug on their romance. Cheating rumors began, but Ryan squashed them immediately, saying that they had problems between just the two of them.

Reese is now happily married to her second husband, Jim Toth, and Ryan is currently dating Paulina Slagter, a 23-year old law student from Stanford. Well at least it worked out for the both of them, albeit with different people.

Madonna & Sean Penn

Madonna-Sean-PennI almost forgot about these two! Madonna and Sean Penn were both big stars back in the 80’s. Of course, Madonna was THE material girl that everybody adored because of her songs. As for Sean, he was amusing as Jeff Spicoli in “Fast Times at Ridgemont High.”

Back in the eighties, I remember reading about their marriage and how abusive and violent their relationship was. They were very mismatched—Madonna wanted to be in the limelight, while Sean valued his privacy. Then in 1987, Sean tied up Madonna inside her home in Malibu and physically assaulted her for nine hours straight with a baseball bat.

Well, for two years of marriage, that ending was very scary and very unnecessary. I’m not sure if Hollywood forgave Sean for what he did, but I sure didn’t. Either way, we all know that the guy is very talented, he just needs to keep his temper in check.

Kim Kardashian & Kris Humphries

Kim-Kardashian-Kris-HumphriesOh, Kim Kardashian and her famous tushie. I don’t know much about her ex-husband, Kris Humphries, but their split back in 2011 surprised me. They were married for only 72 days, but their divorce proceedings lasted far too long. Kris didn’t want a divorce and wanted an annulment instead, stating that Kim only used him to earn ratings for her family’s reality show and committed fraud. Kris only signed the divorce papers in April 2013, after Kim was about to give birth to her daughter, North, with Kanye West.

Most people think that Kim’s marriage to NBA player Kris was her first. It’s actually her second one—so technically, Kanye’s her third husband. A bit confusing, I know. Ah well, who would Kim and her family be without her past failed relationships, right?



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