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25 Of The Oddest Couples In Hollywood

Living the life of a celebrity isn’t always easy. Of course, there’s the light, camera, glam and popularity. But there’s also the paparazzi and tabloids documenting your personal and private life.

Many of these celebrities experienced some of their most important relationships under the spotlight, and the tabloids were there to document every little detail. Here are 25 couples in Hollywood that made the tabloids for being the oddest and most unexpected duos yet!

1. Pete Doherty and Kate Moss. This English musician and American model combo was a relationship that was victimized by tabloids and media. Every move the couple made was documented for the world to see, including their engagement, Unfortunately, after the back and forth, the couple decided to permanently break it off in 2007.

2. Who could forget any of Britney Spear’s relationships? Particularly her marriage to Kevin Federline. While it only lasted for two years, the couple gave birth to two beautiful sons, Sean Preston and Jayden James, and even got their own reality show, Britney & Kevin: Chaotic.

3. Nothing catches the public eye like a couple that doesn’t look like they belong together. Russel Simmons relationship with supermodel Hana Nitsche fits this criteria. The relationship didn’t last long, however, starting up in 2012 and lasting only until 2013.

4. American Idol judge Simon Cowell had a short-lived relationship with 90’s beauty Carmen Electra. The two met on Britain’s Got Talent in December 2012 and dated until February 2013. The relationship lasted a couple months, ending only when Simon was caught cheating with Lauren Silverman, his current baby mama.

5. Nothing turned heads quite like Jessica Alba’s marriage to Cash Warren in 2008. The couple became an outlier in the whirl of Hollywood relationships, as they are still married with two beautiful daughters!

6. Michael Jackson and Lisa Marie Presley in 1975, yet they didn’t get together until the early 90’s. What started as a friendship turned into a romance. While the couple married in 1994, the marriage was short-lived. They divorced only two years later, in 1996.

7. Madonna’s relationship with Dennis Rodman in 1994 was quite the sight to see. Although it only lasted two months, the relationship was highly publicized. In his autobiography I Should Be Dead By Now, Rodman admitted that “Madonna wanted to have my babies.”

8. Katy Perry and Russell Brand were one of those couples that just looked good together. The two of them started dating in 2009, when Perry made a Cameo in Russell’s film Get Him To The Greek. The marriage only lasted two years, however. Perry later admitted that Brand divorced her via text message and never spoke to her again.

9. Courtney Love and Edward Norton started to date after they starred together in The People vs. Larry Flynt in 1996. Love admitted her regrets after they broke up. In an interview, she stated, “I should have married Edwards. I left him for a bad man who stole all my money.”

10. In 2013, Colin Farrell admitted to Ellen Degeneres that he had a short-lived affair with Elizabeth Taylor before her passing. The duo met at an LA hospital, when Farrell’s son was being born. Colin told Ellen, “It was kind of like the last… romantic relationship I had, which was never consummated.”

11. Avril Lavigne and Chag Kroeger dated back in 2012. Sparks flew when the two were writing and recording together for Lavigne’s album. The romance escalated quickly, with an engagement in the works merely after a month of dating. The couple, married in 2013, were split by 2015.

12. Who would’ve thought that the current Kim Kardashian West was once in a romantic relationship with Nick Cannon. Before Cannon grew involved with Mariah Carey, him and Kim had a short-lived relationship from fall of 2006 to January 2007. Cannon later revealed that their breakup was due to Kim hiding the existence of the infamous sex tape.

13. Once upon a time, back in 1999, Jared Leto and Cameron Diaz were engaged. The couple broke up four years later, in 2003, after realizing that their careers were taking them in completely different paths.

14. In 1990, we had quite the duo. Madonna and Vanilla Ice were together for about eight months before breaking up. Vanilla Ice later admitted that Madonna’s 1992 release of her book, Sex, was responsible for their breakup. He claimed to be “embarrassed and ashamed” of his appearance in the book in a suggestive position besides a nude Madonna.

15. A vegas wedding between basketball player Dennis Rodman and Carmen Electra made quite the headlines. Electra later admitted that she was in a dark place when she dated Rodman, in a form of self destruction mode following her mother’s death.

16. Nick Lachey and Kim Kardashian dated for a brief time in 2008, following Lachey’s messy, yet very famous, divorce from Jessica Simpson. Lachey actually implied that Kim used him for publicity, stating “Let’s just say this: We went to a movie. No one foll

owed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside.”

17. Costars Ryan Gosling and Sandra Bullock were involved romantically after starring in a thriller movie, Murder by Numbers, together. They dated between 2002 and 2003, sparking quite the interest in the public eye considering Bullock is 16 a senior to Gosling.

18. Here’s one that was kept quiet: Drew Barrymore and David Arquette. The two secretly dated after co-staring in 1999 movie hit, Never Been Kissed. Arquette has nothing but nice words for her, “She’s just one of the sweetest, kindest people in Hollywood. We used to run around and just be silly.”

19. The one where Monica dated Batman. Courtney Cox and Michael Keaton dated for an amazing six years before they broke up in 1995. “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” Cox said.

20. From 1984 to 1991, Robert Downey Jr. and Sarah Jessica Parker were pretty seriously involved. Downey’s drug use and partying led to a messy breakup after seven years together. The two only made peace 2015, finally becoming civil with one another.

21. Winona Ryder and Matt Damon tried their best to keep two year relationship out of the public eye. “My most recent relationships have not been with famous women, but I was with a very famous woman, Winona Ryder, for a couple of years, and we had a great relationship,” Damon said.

22. Ryan Reynolds and Alanis Morissette met at Drew Barrymore’s party in 2002. They dated for two years, getting engaged in 2004. The engagement never made it to marriage, as the couple broke up by 2007.

23. This one’s a bit shocking: Natalie Portman dated Moby back in 2001. When asked about the relationship, Mod: “I guess in some people’s eyes, [nerds] might be mildly sexy – and, as a nerd, I’m certainly happy to enjoy some of the effects of that.”

24. Kiefer Sutherland and Julia Roberts met on their film The Flatliners in 1990, and got together shortly after. They were engaged that year and planned to get married in the next. However, Roberts broke off the wedding just days before when she found out Sutherland had an affair with a stripper.

25. Before their acting careers took off, Juliette Lewis and Brad Pitt dated for a couple of years. From 1990 to 1993, the couple enjoyed each other’s company but once they both got those breakthrough roles, the relationship fell apart. “It was such a lovely time in my life because we were just unknown young actors in L.A,” Lewis said about the relationship.

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