Surprising Celebrity Couples

24 Surprising Celebrity Couples From The Past Number 24, Cameron Diaz and Jared Leto. We all remember when Cameron and Jared Leto were in a relationship from 1999 to 2003, right? Oh, right. No one remembers that. They were engaged in everything. They apparently parted ways so that Leto could focus on his band, 30 Seconds to Mars, while Diaz's career was beginning to take off. Currently, both of them are doing pretty well for themselves. Number 23, Robert Downey Jr. and Sarah Jessica Parker. From 1984 to 1991, Robert Downey Jr. and Sarah Jessica Parker were in a relationship. He's spoken about the relationship from the past and was quoted saying, We were at a very conservative relationship concerning the fact that she was normal and I was out of my mind. He even went into a little detail about the weird dynamic between him, Sarah Jessica Parker, and Kiefer Sutherland all living together. Awkward. Number 22, Ryan Reynolds and Scarlett Johansson. These two were very private about their love life. So private. But we hardly remember that they were even married. A relationship that began in 2007 and ended in December of 2010. She was only 23 at the time and both had careers on the rise. She suggested in past interviews that their marriage was even a little competitive. How strange would it be if Deadpool and Black Widow were still married? That's not the last we'll see of Ryan on this list, so stay tuned to see who else he was linked to. Number 21, Lindsay Lohan and Samantha Ronson. A relationship that shocked many and faded out of the spotlight fast. The once beloved Disney sweetheart and DJ were on and off again from 2008 to early 2009. Lohan was constantly in the tabloids for her reckless behavior and being with Ronson meant she was attacked constantly. She would later call this relationship quite toxic. She stated that she needed to love herself before she could be in a relationship with anyone. Number 20, Justin Timberlake and Fergie. Does anyone remember that Justin Timberlake and Fergie were together? In 1996, a 16-year-old Justin who was becoming a major heartthrob for teenage girls began dating the 23-year-old Stacey Ferguson, now known as Fergie. She admitted that they, quote, were never serious. He was Mr. Right Now. Seems a little harsh. Looks like they both come out on top though. Number 19, Nick Cannon and Kim Kardashian. The Kim Kardashian and Ray J scandal led this relationship to crash and burn. Apparently, Kim lied to Cannon about the existence of the tape and when he found out the truth he ended things. Little did we all know that that tape was the beginning of a massive Kardashian takeover. Number 18, Vanessa Hudgens and Josh Hutcherson. Did you know that these two young stars used to date? After her very public breakup with Zac Efron, she had a quick relationship with Hunger Games star Josh Hutcherson. It slipped by so fast, a reporter that assumed they were still together asked about their relationship during a promotional interview for Journey to the Mysterious Island. Josh had to awkwardly admit that they were no longer dating. Number 17, Madonna and Vanilla Ice. Believe it or not, Madonna was in a relationship with and then dumped by the Ice Ice Baby singer in the early 90s. No one can say that Vanilla Ice was a saint himself back then, but said he broke up with Madonna because he didn't want to be part of her, quote, slutty package. Fast forward to today and Madonna obviously had the last laugh. Number 16, Michael Buble and Emily Blunt. Michael and Emily spent three years together and split in 2008. Many rumors about Buble cheating were starting to circulate, who even remembers that they were together? In 2015, Michael denied the cheating allegations, saying that they just weren't right for each other. It's great that it didn't work out though, because she married Jim from The Office, aka John Krasinski. Number 15, Ryan Gosling and Rachel McAdams. We all thought we wanted the Ryan and Rachel couple to work. That is, until we found out how absolutely perfect him and Eva Mendes are. Seriously, couple goals. Rewind back to Ryan Gosling and Rachel McAdams dating. They were co-stars on the most romantic film on Earth, The Notebook, and began dating after filming was done, and stayed together for almost four years. Fun fact, Ryan and Rachel did not get along on the set. Gosling even asked for her to be replaced with another actress. Number 14, Janet Jackson and Matthew McConaughey. Seems like her killer abs drew McConaughey to her. In 2002, the duo met at the Grammy Awards, and that meeting prompted a rumored steamy night at her home in Bel Air. A witness said he left her home shirtless, carrying his shoes and whistling. Yep, sounds like Matthew McConaughey. He denied the romantic rumors at the time, but recently Jackson let it slip that they were more than just friendly that night. Number 13, Scarlett Johansson and Josh Hartnett. From 2005 to 2007, Johansson dated Josh Hartnett. Josh Hartnett made a habit of dating his uber famous and beautiful co-stars, which is something he said he doesn't recommend. Scarlett Johansson said that their breakup was, quote, very painful. While he disappeared from the limelight for a few years, she went out to do hit movies like The Avengers and Her. Number 12, Sofia Vergara and Enrique Iglesias. Back before Enrique even dated Anna Kournikova, he dated the now modern family star Sofia Vergara. Everyone knew Enrique Iglesias' name then, and she was just a beautiful actress from Colombia. Now, Sofia Vergara is a household name and is married to the very buff Joe Manganiello. She's done well in life. Number 11, Jake Gyllenhaal and Reese Witherspoon. Yes, that's actually how you pronounce his last name. The actor who's been drawn to more and more dark roles lately, and the girl who won all our hearts and cruel intentions, were a thing for a bit. After they met on the set of Rendition, they did end up splitting on healthy terms, which is obvious when Gyllenhaal said this about Witherspoon, quote, she is, as I would say, about most of the women who I'm close friends with or had relationships in my life, one of the smartest, strongest people I've ever met. Number 10, Macaulay Culkin and Mila Kunis. In 2002, the 18-year-old and the 20-year-old started dating when Mila Kunis was still filming for That 70s Show. Macaulay Culkin was one of the biggest stars in the world at the time, and they could hardly walk down the street together without fans freaking out. They had an eight-year relationship that ended in 2011, and a lot of that had to do with the fanatic fans. Number 9, Evan Rachel Wood and Marilyn Manson. The star of the very popular HBO show Westworld wasn't always a kick-ass robot who only had cowboys to give affection to. Evan Rachel Wood dated and was even engaged to the Beautiful People singer, Marilyn Manson. They had an 18-year age difference, but that wasn't the only thing that prompted criticism. Manson had recently divorced his wife, Dita Von Teese, and a huge backlash hit the then 18-year-old star. They split for good in 2011, and Evan said she had no regrets about the relationship. Number 8, Bradley Cooper and Renee Zellweger. The Hangover star and the Bridget Jones star were once a couple from 2009 to 2011. Their few years together seemed to take a backseat to Bradley's career. He worked hard to become a leading man, and Renee was a supportive girlfriend. But the relationship just didn't make it. Number 7, Nicolas Cage and Brooke Shields. Brooke Shields was the ideal woman in the 80s, and she dated Nicolas Cage. The relationship began in 1987, but only lasted till the next year. Nicolas Cage had a unibrow back then, so maybe that had something to do with it. Number 6, Demi Moore and Ashton Kutcher. Before Ashton Kutcher was married to his now-wife Mila Kunis, he was married to Demi Moore. Despite the large age gap of 16 years, they were lovestruck back in 2003. Their 8-year relationship ended in 2011 after many rumors about Ashton cheating surfaced. Number 5, John Mayer and Jessica Simpson. John Mayer and Jessica Simpson were an on-and-off-again couple in 2006 for about 9 months. John Mayer has a record of being a jerk about his ex-girlfriends, but his most memorable stint was with Jessica. Number 4, Paul Rudd and Jennifer Aniston. Jennifer Aniston herself revealed that her and Paul Rudd dated when they were like 12. It must have ended on good terms because he ended up being her co-star on the TV show Friends, the object of my affection, and the very hilarious Wanderlust. Number 3, Ryan Reynolds and Alanis Morissette. Ryan Reynolds and Alanis Morissette were almost married. In 2002, they hit it off at Drew Barrymore's birthday party and were engaged two years later. It seemed like everything was going well for the two lovebirds, but their reps publicly announced their separation in February of 2007. Number 2, Rihanna and Shia LaBeouf. Now, let's all take a step back and try to imagine what this relationship would look like if it had succeeded. Crazy. These two only had one date 10 years ago and Shia has been quoted saying, quote, the spark wasn't there. He did admit he was infatuated with her before the date though. Aren't we all? Number 1, Madonna and Tupac. The one and only Madonna. Can she get any cooler? Yes, she can. She was once romantically linked to Tupac in the early 90s. Madonna revealed the relationship to Howard Stern almost 22 years to the day of when she first met the iconic rapper. She said that he had her, quote, all riled up about life in general.