12 Of The Most Notorious Hollywood Breakups

Ending a marriage or relationship is rarely an easy thing. It’s especially challenging when you’re a celebrity, and the public is interested in virtually every aspect of your life. As a star, you’ve got to figure out who is entitled to which assets in the divorce and try to at least remain civil if you know you’re going to be in the same professional and personal social circles with your ex. If there are children involved, you have to do what is necessary to make sure the kids know that they are loved no matter what, and work out a schedule that allows the children to spend quality time with both parents. Yes, these are also things “normal” people have to go through when they decide to end a relationship. However, when there are cameras in your face constantly, as well as entertainment websites and blogs printing information about your personal life that may or may not be true, you’ve got even more stress on your hands.

There are also those Hollywood breakups that people can’t seem to stop talking about, even when it’s clear that both celebs have moved on with their lives. Sure, it keeps these stars relevant, but it’s safe to say they’d probably prefer another method for maintaining their fame. Here are 12 of the most notorious Hollywood breakups.


12 Samantha Ronson and Lindsay Lohan

Lindsay Lohan and Samantha Ronson had an on-again, off-again relationship that was filled with drama and arguments. Eventually, Ronson got tired of fighting and called the whole thing off for good. Lohan then Tweeted that Samantha “won” and that she’d broken her heart. Lindsay also admitted that she loved Ronson. During an interview, she stated that she and Samantha were taking a “brief” break so that Lindsay could focus on getting herself together. They’re still on a “break,” because Lindsay Lohan still hasn’t gotten it together, even after getting a special on OWN and second chances from producers who didn’t want to work with her before.

11 Jennifer Aniston and John Mayer

Aniston fans got so excited when the actress met John Mayer while promoting her film Marley & Me. Mayer even flew to Miami to see Jennifer, which led people to believe that the relationship was getting serious. Fans of Jennifer were likely happy to see that she was finding love again, but John Mayer is known for a lot of things—and love isn’t one of them. The couple’s romance was short, and Aniston even told a British magazine, “who said that every relationship has to last forever? That’s hoping too much.” That’s a pretty mature attitude to take, especially when you’ve dated someone who is so…immature.

10 Jon and Kate Gosselin

Remember when you could barely turn on the TV without hearing about “Jon and Kate Plus 8?” Yeah, those days are over. The former couple was married for 10 years, and during that time, they had a set of twins and a set of sextuplets. That’s enough stress to lead anyone to make some irrational and emotionally charged decisions. Apparently, Jon started checking out of the relationship (which was probably due to the fact that he suddenly had eight children), and even though the two renewed their vows on their reality show, it wasn’t enough to keep the family together. Jon is apparently taking odd jobs to make ends meet, and Kate recently ended another show with TLC, featuring her and the kids.

9 Nick Lachey and Jessica Simpson


There was once a time when reality shows featuring very private aspects of people’s lives was unheard of. That is, until Simpson and Lachey debuted their reality show, Newlyweds. We got a glimpse into their wedding day preparation, and the comical and challenging moments that come with merging your life with someone else’s. However, we also learned that it’s probably not a good idea to expose your marriage to the entire world, especially when it’s brand new. The relationship was over in 2005, and both celebs have stated that they don’t talk to each other at all anymore. That must have been a pretty nasty breakup. Both Simpson and Lachey have married and had children with other people since then.

8 Reggie Bush and Kim Kardashian

The pro football player and reality star were together for two years and talked about getting married. In 2009, they called off their relationship, but there were soon reports that they’d gotten back together. There were even a few episodes of Keeping Up With The Kardashians, in which Kim exchanged some emotionally charged phone conversations with Bush about the problems in their relationship and how much she loved him. Obviously, Kardashian has moved on—several times—but is now married to Kanye West. The two have a daughter named North and a baby boy on the way. Reggie Bush got married as well—to a woman who looks a lot like Kardashian—and has a daughter as well.

7 Kid Rock and Pamela Anderson


Kid Rock and Pamela Anderson were only married for a few months before they decided that it just wasn’t working out. They got a divorce in November of 2006, after having a beautiful ceremony on a yacht in St. Tropez. Even so, Anderson refers to the event as “the best, most romantic wedding of all time.” Some say that Kid Rock married Pamela to boost his career, which worked for a while, but we haven’t heard much from him in a while. Anderson has since adopted a more conservative image, and is working with celebrities like Bob Barker to promote animal rights.

6 Britney Spears and Kevin Federline

Some would say that Spears and Federline’s relationship was doomed from the start. Britney allegedly “stole” Kevin, who was a backup dancer for her, from his then-fiance (and mother of two of his children), Shar Jackson. In 2009, Britney filed for divorce from Kevin, after being married to him for just two years. She cited “irreconcilable differences” as the reason. Spears and Federline have two sons together, and apparently, the divorce came as a shock to Kevin (she texted him that it was over while Federline was conducting an interview). Spears stated that she “married for the wrong reasons” and wasn’t following her heart when she decided to become Kevin’s wife. Even though they’ve both moved on, Federline will always be known as “Mr. Britney Spears.”


5 Gwyneth Paltrow and Brad Pitt

Remember back in the 1990s when Brad Pitt and Gwyneth Paltrow were one of the “it” couples in Hollywood? Sometimes they even wore similar hairstyles. They met on the set of Seven in 1995, and dated for two and a half years before calling it quits. As we know, Pitt moved on to Jennifer Aniston and was married for a few years before meeting Angelina Jolie on the set of Mr. and Mrs. Smith and starting a relationship with her. Some of his fans still haven’t forgiven him for that, even though Aniston is now married to Justin Theroux. Gwyneth married Coldplay frontman Chris Martin, but the two have since “consciously un-coupled.”

4 Billy Bob Thornton and Angelina Jolie

Bombshell actress Angelina Jolie and irreverent actor Billy Bob Thornton, decided to end their marriage in 2002. Jolie filed for divorce, citing “irreconcilable differences” but the two are now on good terms. Angelina and Billy Bob also adopted a son named Maddox from Cambodia, who was 11 months at the time of the divorce, and Jolie requested full custody of him. The former couple met on the set of Pushing Tin in 1999, and got matching tattoos (Angelina has since had hers altered). Of course, Jolie went on to another high-profile relationship with heartthrob actor Brad Pitt. The two adopted more children, and also have three biological children together.

3 Reese Witherspoon and Ryan Phillippe


When Witherspoon and Phillippe met on the set of Cruel Intentions as young actors, their romance blossomed, much to the delight of their fans. They were married for seven years, but filed for divorce in 2006, to the shock of their admirers. The former couple have two children together, and there were allegations of infidelity on Ryan’s part. Phillippe has since been seen dating a few of the stars from the Twilight movie franchise, and Reese has since married Jim Toth. She has a son with Toth, and recently made the news for getting pretty snarky with an officer when her husband was pulled over for driving while under the influence of alcohol. At least she wasn’t getting negative press like that when she was married to Phillippe, but cheating is often the quickest way to end a marriage, so there’s that.

2 Megan Fox and Brian Austin Green

Male fans of Megan Fox were probably rejoicing when they heard the news that the actress and model was separating from her actor husband, Brian Austin Green. They have two kids together, and were engaged back in 2009—and they broke up then, too. Apparently, they worked things out and tied the knot, but they just couldn’t make it last. According to rumors, Fox wanted to have an open marriage, and initially, Green was OK with that. We’re guessing he came to his senses and realized that no man in his right mind would want his woman sleeping with someone else—especially when virtually any man would jump at the chance to be with her.

1 Brad Pitt and Jennifer Aniston


These two stunning actors tied the knot in 2000, during a lavish ceremony in the summer of 2000. Five years later, they were divorced. There’s still that theory going around that suggests Pitt found Angelina Jolie more interesting when they met while filming Mr. & Mrs. Smith. Ironically, they later became Mr. & Mrs. Pitt. However, there are still so many people who are Team Jennifer when it comes to this sordid love triangle. Remember when Brad Pitt appeared on an episode of Friends, when he and Aniston were still married? He pretended that he hated her in the episode. We should have seen it coming.


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