15 Craziest Celebrity Ex-Boyfriends In Hollywood History

The internet is full of stories of crazy ex-girlfriends who are obsessive, needy, jealous, and, well, crazy. Most guys have their “crazy ex-girlfriend story” (sometimes several) that may make you feel bad for them at first but then, one day, you realize that there is no way that all these stories could be true. Really--every girl you ever dated was crazy? In these relationships, the guy is most likely emotionally manipulative, withholding affection, never calling, posting photos with other girls, or always hanging out with the guys instead of going out for a date night. Then they make you feel like you’re the crazy one. What about all of the crazy ex-boyfriends? Where are all the stories about them? You don’t hear many stories from girls about their crazy exes--probably because no one believes them. Whenever a girl is clingy and needy, she comes across as pathetic. But when a guy is needy and clingy, he comes across as sweet and in love. Everyone loves to read the stories about nasty breakups and divorces in Hollywood and they also love listening to the songs Taylor Swift writes about her crazy ex-boyfriends and then the public subsequently shames her for it. Sure, T-Swift’s stories may be embellished but what about all of the men who have sung nasty songs about their exes? Ray J, John Mayer, Ed Sheeran, and countless others. No one bats an eye. It’s time to set the record straight and take a good look at the craziest celebrity ex-boyfriends (and ex-husbands) in Hollywood history.

15 Justin Bieber

via Billboard

We all know that the Biebs is a bit of a wild card. After vandalizing a building in Brazil, letting loose in a mop bucket in a nightclub kitchen, and being a general disgrace to the entire country of Canada, he went and broke the heart of Selena Gomez. Definitely the biggest mistake he ever made. You can’t feel too bad for Selena though because she’s handled the entire relationship like a champ and has moved on to bigger and better things, namely The Weeknd. Bieber, on the other hand, can’t seem to let it go. He decided to play the part of the heartbroken ex even after all these years in order to garner sympathy but he acts more like a spoiled child than a jilted lover. Ever since Gomez’ relationship with The Weekend went public, Bieber has been on the attack. He even went so far as to say that he doesn’t even like The Weeknd’s music and called it “whack”. Come on, Justin, we know you've jammed out to “The Hills” at least once. Talk about petty.

14 Chris Brown

via Billboard

This list would be incomplete without one of the worst boyfriends in the history of boyfriends. The fact that Rihanna had a restraining order against Chris Brown should be enough for anyone to conclude that he is a crazy ex-boyfriend but his abusive relationship with the famous singer is just the tip of the iceberg. As much as everyone loved “Forever”, it was clear that the public was on Rihanna’s side after the pictures of her busted lip and bruised face appeared in the media and details came out about the night in 2009 when Brown brutally beat her after they got into an argument. However, once Brown had given his obviously scripted apology in a YouTube video, he began to play the victim and he's been playing the victim ever since. When he was set to appear on Good Morning America, he was so angry about the questions regarding his history of violence that he threw a chair through the studio window. What makes it all so much worse is that he still managed to weasel his way back into her life again and again and has never showed real remorse for his actions.

13 Frank Sinatra

via MirrorUK

Let's go way back to the 1970s. Frank Sinatra was one of the most famous people in the world after being a teenage heartthrob to Academy Award winning actor. He has already had very public relationships, most notably his marriage to Ava Gardner. They were basically the Brangelina of their day. It would seem that the two were driven apart thanks, in no small part, to Sinatra’s raging jealousy which led him to bug her phone and hire a private investigator to catch her talking to other men. As Sinatra was getting older, he met a young Mia Farrow and the two became an item. She was a hip aspiring actress with a short mod haircut and he was a huge but aging star from a different generation. Needless to say, they didn’t stay together. Sinatra wanted to revive his acting career so he produced a movie that he would also star in and wanted Farrow to star in it with him. She decided, however, to star in a little movie called Rosemary’s Baby. While she was on the set, Sinatra sent her divorce papers. In the end, Farrow chose her career over her relationship but only because Sinatra's old habits die hard. He was much too possessive and jealous to let his actress girlfriend be a big Hollywood star in her own right.

12 Johnny Depp

via X17

The star of a dozen bad movies that failed at the box office (Honestly, did anybody see Mordecai?) with teeth that, by many accounts, appear to be rotting in his face. Though he went through some high profile relationships in the past with Winona Ryder and Kate Moss, he settled into a 14 year relationship with Vanessa Paradis. Then there was The Rum Diary (another bad Johnny Depp movie) and he met Amber Heard. The two were married two years later. After a short lived relationship, Heard claimed that she had been physically assaulted by Depp (one of the assaults was captured in a video) and filed for divorce. Of course, there are many who claim that Heard is a gold digger (even after she gave all of the money from the settlement to charity) and that she is a liar (even though the claim and eventual divorce has already hurt her career more than help it). Exes and friends came out of the woodwork to say that Depp would never do such a thing and many claimed that Depp just didn’t seem like the kind of person who would physically abuse anyone. But, as many domestic abuse victims will tell you, the kind of men who are abusive rarely ever come across that way.

11 Rob Kardashian

via Gossip On This

Long before Rob ever met Blac China, he was in a relationship with Rita Ora. If you don’t know who Rita Ora is, well, you’re not the only one. She’s a singer, a TV host, a model, a brand ambassador, an actress, and also, according to some misinformed individuals, “Becky with the good hair”. She does a little bit of everything without really being known for any of them. So she and Rob should have been perfect for each other, right? Wrong! The two split after just a few months of dating and Rob showed his crazy side on Twitter when things went sour. He angrily tweeted that she had cheated on him with “nearly 20” guys and also referred to her as Rita “Whora”. These tweets have since been deleted and none of his claims have been proven but he STILL talks about it. On an episode of Rob & China he said, “I had a really bad past relationship where the girl was cheating and having physical relationships with so many people.” Obviously another dig at Rita Ora. Even if his suspicions were true, going on a rant on Twitter and shaming your 22 year-old ex is so immature and, frankly, crazy.

10 Tom Cruise

At this point, everyone knows that Tom Cruise is, at the very least, eccentric. The star is known for his association with the Church of Scientology and also for jumping up and down on Oprah’s couch. Let’s not forget his highly publicized relationships with Nicole Kidman and Katie Holmes. As if these relationships are not enough to confirm him as the epitome of the “crazy-ex”, his relationship with Iranian actress Nazanin Boniadi is the icing on the cake. Their relationship, though highly disputed, was confirmed by multiple sources including Leah Remini. The story goes that Boniadi was a member of the Church of Scientology and she was deemed the perfect candidate for Cruise’s new girlfriend. She was forced into a bizarre courtship with Cruise, was quickly moved into his home, but it wasn’t meant to last. Long story short, the leader of the church and Cruise’s bff, David Miscavage, decided he didn’t like the new girlfriend. Members of the church then came to Boniadi to tell her that Cruise was breaking up with her and he wanted her to move out. That was the last time she ever heard from him. The church adamantly denies the claim but, as bizarre as this story seems, it's not completely off brand for the Church of Scientology.

9 Eddie Fisher

via The Sun

The story of Eddie Fisher and Debbie Reynolds is a crazy ex story of the ages. Back when Reynolds was a Hollywood superstar and Fischer was a famous nightclub crooner, the two were married. The couple was good friends with Elizabeth Taylor and her husband Mike Todd and the foursome spent a good deal of time together. However, in 1958, Todd was killed in a plane crash and Taylor was distraught. While Reynolds offered to care for her three children, Fischer stepped in to console the grieving widow. As you may have guessed, his role as the consoler turned into that of the lover and he swiftly moved in with the most beautiful woman in the world. At this point, Reynolds and Fischer had two children (Carrie Fisher and Todd Fisher) of their own but that didn’t stop him from moving on with the widow of his recently deceased friend. However, things didn’t turn out so great for Fisher. Taylor left him for Richard Burton soon after they were married and Reynolds came out on top since she married Harry Karl, a wealthy business man. Serves him right.

8 Kanye West

via InTouch Weekly

Before Kanye West married Kim Kardashian and before Amber Rose married Wiz Kahlifa, West and Rose looked to be very much in love while they dated between 2008 and 2010. We don’t know why they broke up but it’s fair to say that it wasn’t amicable. For some reason, he is still consistently dragging Rose for her choice of work and even went so far as to drag her ex Khalifa during a rant on twitter that included some nasty remarks about their intimate relationship. This is in reference to the fact that the two have a son, Sebastian, together. However, Rose has never let anyone walk all over her and she always stands up for herself and her relationship with Khalifa. For some reason, West cannot stop talking about this relationship and he even said in a 2015 interview, “Its very hard for a woman to want to be with someone that’s with Amber Rose. I had to take 30 showers before I got with Kim.” Seriously, Kanye, let it go, you’re embarrassing yourself.

7 Howard Hughes

via Fine Art America

This entrepreneur, business man, aviator, director, and billionaire is known for his flings with famous women including Katherine Hepburn, Bette Davis, Ava Gardner, Ida Lupino, Rita Hayworth, Yvonne De Carlo, Olivia de Havilland, and Joan Fontaine. It is probably fair to say that all of these women thought of him as their crazy ex. Sure Hughes suffered from OCD for much of his life which made him come across as eccentric but that’s not why he’s a crazy ex-boyfriend/ex-husband. So why then? For starters, he punched Gardner in the face, dated sisters Havilland and Fontaine at the same time, hooked up with Lupino and Faith Domergue when they were underage, slapped De Carlo twice then hid in her bathroom, and also tried to hook up with Debbie Reynolds while his wife Terry More was pregnant. He was known for showering his girlfriend-of-the-week with gifts then moving onto the next girl without exactly letting either of the girls know. That’s enough crazy to be labeled as a crazy ex-boyfriend, don’t you think?

6 Tyga

via The Inquisitr

The fact that Tyga and Kylie Jenner began dating when Jenner was only 17 is crazy (and disgusting) enough but that’s just the tip of the iceberg for her sleazeball boyfriend. The two have been in an on-and-off relationship for the past three years and they are currently in the midst of another break. It’s rumored that Jenner is seeing rapper Travis Scott but they also said the same thing about her and rumored boyfriend PARTYNEXTDOOR last year but that turned out to be nothing. What makes him the crazy ex is that every time they’re on a break, the next day he’s immediately photographed with another sexy model. This kind of behavior is incredibly a manipulative and cruel means of making your 19 year-old ex jealous, even if your ex is a huge reality TV star and cosmetics mogul. Let’s also not forget that Tyga left his baby mama and finance Blac Chyna for the 17 year-old. Say what you will about Kylie and Blac Chyna but they both deserve better than Tyga. Good riddance.

5 Cary Grant

via The Hollywood Reporter

When Cary Grant was 52, his wife Betsy Drake wrote the script for Houseboat which they were supposed to star in together. However, after Grant met Sophia Loren, he cast her in the part that his wife was supposed to play. To make matters worse, he hired a new screenwriter to rewrite the script. Drake didn’t get any credit for her work. Grant tried to convince Loren to marry him but the 22 year-old turned down the 52-year-old actor to marry Carlo Ponti, an Italian film producer. When she died at age 92, Drake claimed that she had given up acting to marry Grant and she tried to please him by being a housewife. She even claimed that he “fell asleep after dinner and preferred television to talking with me” in her filing of the divorce. As if leaving your wife for another woman isn’t bad enough, he twisted the knife by essentially firing her as both the lead actress and the writer of the film. Crazy.

4 Joe DiMaggio

via Parade

When Marilyn Monroe was at the height of her career, she married New York Yankees superstar Joe DiMaggio. One of the biggest red flags of their relationship was the fact that DiMaggio thought of Monroe like the entire world thought of her: a goddess. He held her to a standard that she could not possibly reach but he was also uncomfortable with the fact that she was seen as a desired symbol by the entire world. The idea of his superstar wife cheating on him drove him crazy. He read all of her fan mail, hated when she wore provocative clothing, and wanted her to give up acting and be a housewife. During this time, Frank Sinatra was going through a similar experience with his then girlfriend Ava Gardner and it was Sinatra who advised him to start recording her phone conversations and hire a private investigator to follow her. There was also a rumor that DiMaggio had a life-like doll made to look like his ex-wife but it has never been confirmed. However, it seems that a lifeless and obedient mannequin that looked like Marilyn Monroe was exactly what he wanted in the first place.

3 Justin Timberlake

via Huffington Post

It's common knowledge that Justin Timberlake wrote “Cry Me a River” about Britney Spears but he’s the one who keeps crying. It’s been fifteen (fifteen?!) years since their highly publicized split but he is still talking about it. Sure, we can expect ramen-noodle haired Justin to be upset about the breakup when it happened all the way back in 2002 but he has been playing the victim for over a decade. He brought her up in 2003, calling her a “horrible woman” during a Barbara Walters interview, wrote another hate song ("What Goes Around...Comes Around") about Spears in 2006, said in 2008: “The world has always been full of Madonna wannabes, I might have even dated a couple”, then he brought her up again in 2016 when he talked about “the pain” he was in while writing “Cry Me a River.” What’s worse, this obsessive obnoxiousness is often seen as love and Timberlake is really a hurt and jilted lover. Seriously? It’s been 15 years. Time to move on.

2 Sean Penn

via UsWeekly

Back when Madonna was the biggest pop star in the world and an aspiring actress, she married up-and-coming actor Sean Penn. One night when Madonna told Penn that she was leaving the house, he assaulted her, tied her to a chair with twine, left to buy more alcohol, then returned only to continue abusing her. After hours of torment, he finally agreed to untie her but only after she promised to be intimate with him. When she was free, she escaped. Penn was charged with domestic assault but Madonna dropped the charges. Why? Because he was about to serve 60 days in the Los Angeles County Jail for reckless driving and punching an extra on the set of one of his movies. Though Madonna denies most of the events now, at the time she filed a report with the Malibu sheriff’s office that Penn had told her that he owned her “lock, stock, and barrel.” The two appear to be on good terms at the moment but that doesn’t let Penn off the hook. He’s definitely a crazy-ex.

1 Nick Loeb

via New York Post

Before Sofia Vergara of Modern Family met and married the hunky actor Joe Manganiello, she was with a wealthy business man named Nick Loeb. After the split, the two were engaged in a nasty custody battle but not the kind of custody battle you would expect. While the two were still together, the couple created frozen pre-embryos and Loeb wanted full-custody of the viable pre-embryos in order to bring them to term. Loeb also filed a right-to-life lawsuit against Vergara because she would not allow him to have custody of the pre-embryos. He even went so far as to name them Emma and Isabella and planned on implanting them in a surrogate. Fortunately for Vergara, the act of attempting to implant these pre-embryos into a surrogate, create trusts for them, and name them without her consent, he broke the terms of the contract which meant that Loeb didn’t have a leg to stand on. Talk about crazy.

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