15 Most Notorious "Players" In Hollywood

All over the world, people are searching for their one true soulmate, the one love they’ll spend each moment of their life with. Not one second will go by without them talking. They never ever want to be apart and often dream of one day growing old together. Then, there are the people all over the world that are completely sickened by that idea.

For some people, it might be a little hard to settle down. They just enjoy dating different people a lot. Not everyone can find their soulmate and some people don’t even want to. Celebrities are no different when it comes to relationships. Some are searching for their soulmate and some are just looking for a friend…that they can make out with. Celebs have to deal with the media and fans all being obsessed with their relationships. It’s not easy to have everyone watching their every move. There are several celebs that are serial daters. Celeb serial daters or “players” will go from person to person in a short amount of time. They don’t stay around for too long and get out before things can get too serious. Each relationship is more high profile than the last and gains even more attention. In many cases, these players have even managed to get married. Most of those marriages didn’t last long and it was over before it even really started. Of course, the most legendary celebrity player, George Clooney, actually retired from the single life and is now married. However, for the celebs on this list, it’s still to be seen. Here is a look at 15 Most Notorious Celebrity “Players” in Hollywood.

15 Kim Kardashian


Socialite Kim Kardashian has dated pro athletes, models, and musicians. Kim’s taste in men is similar to Kanye West’s music. It’s a wide range of various genres and experimental music. Kim Kardashian is a reality TV personality best known for her appearances in Keeping Up with the Kardashians and the series' numerous spin-offs.

Kim Kardashian has been married several times starting with Damon Thomas from 2000 to 2004. In 2007, an infamous s*x tape she had made with singer Ray J was leaked. In 2011, she was married to NBA star Kris Humphries for 72 days before getting a divorce. In 2014, she married her current husband Kanye West. She was in serious relationships with football player Reggie Bush and pro footballer Miles Austin. She also dated singer Nick Lachey and musician/actor Nick Cannon. She has been rumored to be involved with a plethora of celebs, including Joey Lawrence, Gabriel Aubry, The Game, and 50 Cent.

14 Lil Wayne


Lil Wayne has sold over 100 million albums worldwide, joined Cash Money Records at the age of 9, and has broken several industry records. However, his greatest record might be the long list of women he’s dated. Lil Wayne is best known for releasing several popular singles, such as “Go D.J.,” “Lollipop,” and “A Milli.” He is widely regarded as one of the best-selling artists of all time.

Lil Wayne seems to have difficulty settling down and enjoys the dating life. Lil Wayne has four children from four different women. At the age of 16, he had his first child with reality star/rapper Toya Carter. His other baby mamas include radio personality Sarah Vivan, actress Lauren London, and singer Nivea. He dated rapper Trina who he also got pregnant but had a miscarriage. In 2014, he was dating singer Christina Milian until they broke up in 2015. Additionally, he has dated model Tammy Torres, singer Shanell, and former video vixen Karrine Steffans.

13 Blac Chyna


Video Vixen and model Blac Chyna has been involved with athletes, rappers, and reality TV stars. She’s come very close to getting married but always gets out just in time. She is best known for appearing in numerous music videos for several rappers, including Kanye West, Future, and Nicki Minaj. She also launched her own boutique, 88Fin, which features her own clothing line and products. Additionally, she launched her own adhesive eyelash line, LASHED.

In 2011, Blac Chyna started dating rapper Tyga after being featured in his music video “Rack City.” They have one child together and were engaged but eventually broke up in 2014. In 2016, she became engaged to Robert Kardashian after dating for 3 months. They have one child together but broke up at the end of 2016. She also dated musician Drake, NBA star P.J. Tucker, and rapper Future. Rumors suggest that she’s been involved with rapper Game and boxer J’Leon.

12 Lindsay Lohan

For roughly a year, she dated singer Aaron Carter. In 2004, she dated actor Wilmer Valderrama, and later dated Hard Rock Café heir Harry Morton. She then dated snowboarder Riley Giles right after dating British TV personality Calum Best. She also dated actress Courtenay Semel and DJ Samantha Ronson. Her mother claims that she was dating Heath Ledger at the time of his death but she denies this. She has been rumored to have been involved with Leonardo DiCaprio, Seth Rogen, and Joaquin Phoenix. In 2014, a list surfaced online that was supposedly written by Lohan while at a hotel. It’s a list of her 36 lovers, which includes Justin Timberlake, Adam Levine, Orlando Bloom, and Ashton Kutcher.

11 50 Cent


50 Cent has dated several of the most beautiful celebs in Hollywood. He’s just not a one-woman man. He enjoys the company of women a lot and it seems hard to give up for him. 50 Cent has released several popular albums, such as Get Rich or Die Tryin’, The Massacre, and Before I Self Destruct. He also starred in the semi-autobiographical film Get Rich or Die Tryin.

In 2003, 50 Cent dated actress Vivica A. Fox and they were often seen together at various events and awards shows. In 2010, he dated comedian and talk show host Chelsea Handler. From 2011 to 2012, he was involved with model and actress Daphne Joy. They have one child together. He has been linked to several celebs, such as Joy Bryant, Megan Good, and Naomi Campbell. He has also been rumored to be in a relationship with some of the most famous celebs in the world, including Paris Hilton, Kim Kardashian, and Beyoncé.

10 Wilmer Valderrama


Wilmer Valderrama is best known for his portrayal of foreign exchange student Fez on the Fox sitcom That 70’s Show. In the early seasons of That 70’s Show, the running joke was that Fez was doomed to be a virgin forever. Fez could barely get any woman to look in his direction. Wilmer, on the other hand, goes through women like Fez went through candy. Wilmer has appeared in several films, such as Party Monster, Larry Crowne, and The Adderall Diaries. He currently starts in the horror series From Dusk Till Dawn.

Wilmer Valderrama has dated several gorgeous actresses, including Jennifer Love Hewitt and Minka Kelly. In 2004, he began dating singer and actress Lindsay Lohan. Later, he was in a relationship with another singer and actress, Mandy Moore. Wilmer seems to have a thing for hot singers as he also dated Avril Lavigne and Ashlee Simpson. From 2010 to 2016, he was in a relationship with singer and actress Demi Lovato.

9 Amber Rose

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Former video vixen Amber Rose is busy breaking hearts. She has gone from celeb to celeb in a short amount of time. It’s not her fault that she has celebrities trying to knock down her door just to get a glimpse of her. She has appeared in music videos for several different artists, such as Ludacris, Nicki Minaj, and Young Jeezy. She is also a model and has posed for Louis Vuitton. She also briefly hosted The Amber Rose Show.

From 2008 to 2010, Amber Rose was in a relationship with rapper Kanye West. He discovered her after she appeared in Young Jeezy's video for “Put On” featuring West. In 2013, Amber married rapper Wiz Khalifa after dating for several years. The much talked about relationship ended in 2014. Amber and Wiz have one child together. Additionally, she dated singer Chris Brown and rapper Fabolous. She was also involved with basketball player Amar’e Stoudemire and football player Reggie Bush.

8 Michelle Rodriguez


In an interview with Entertainment Weekly, she stated, “I’ve gone both ways. I do as I please. I am too curious to sit here and not try when I can. Men are intriguing. So are chicks.” In other words, she’s been really busy. Most of her relationships are short and never last too long. She was previously in a relationship with Fast and Furious co-star Vin Diesel. She went on to date several famous celebs, including actors Colin Farrell, Oliver Martinez, and singer/actor Lenny Kravitz. She had also been involved with actor and singer Zac Efron and months later, was involved with model Cara Delevingne.

7 Joe Jonas

In 2006, Joe Jonas dated singer and actress AJ Michalka. In 2008, he was in a high profile relationship with fellow player Taylor Swift. He apparently broke up with her over the phone. From 2008 to 2009, he dated actress Camilla Belle. In 2010, he began dating the utterly beautiful Demi Lovato before dating Ashley Greene until 2011. In early 2017, Joe Jonas revealed that he was now dating Game of Thrones actress Sophie Turner. He has also been linked to Blanda Eggenschwiler, Dulce Maria, and Brenda Song.

6 Rihanna


Rihanna’s taste in man is like her music. It covers a very wide range of different genres. She is one of the best-selling artists of all time and has released several critically and commercially acclaimed albums, such as Good Girl Gone Bad, Loud, and Unapologetic. Rihanna has received a plethora of awards, including 8 Grammy Awards, 12 American Music Awards, and 12 Billboard Music Awards. She has dated almost as many celebs as she’s won awards.

In 2008, Rihanna started to date singer Chris Brown that first ended after he physically assaulted her hours before the 51st Grammy Awards. Brown was later charged. However, they briefly rekindled their relationship before breaking up. Later, Rihanna dated rapper Drake who professed his love for her at the MTV Video Music Awards. She was later in a short-term relationship with MLB player Matt Kemp from 2009 to 2010. Additionally, she’s dated Shia Labeouf, Travis Scott, and Josh Hartnett.

5 Derek Jeter

In 2000, 5-time World Series Champion Derek Jeter won the World Series Most Valuable Player Award. Nobody deserves the Most Valuable “Player” Award more than Derek Jeter. Just take a look at all of the hot and beautiful women he’s dated. Derek Jeter is a retired baseball player who has played for the New York Yankees for 20 seasons. He broke numerous records and has played a crucial role in the success of the Yankees in the 90’s and 2000’s. He is also quite the ladies man and has been very successful in that department.

From 1997 to 1998, he dated R&B icon Mariah Carey in a highly publicized relationship. He then dated glamour model and video vixen Vida Guerra. Not too long after, he started dating Miss Universe 2000 Lara Dutta. He has also dated some of the most beautiful actresses, including Minka Kelly, Jordana Brewster, and Jessica Biel. He has also been linked to model and TV host Vanessa Minnillo and singer Joy Enriquez. In 2016, he married model Hannah Davis. Apparently, Jeter is now retired from both baseball and being a player.

4 John Mayer


It’s inevitable that one day, John Mayer will be included in the Hall of Fame. Not the Rock and Roll Hall of Fame but the “Player’s” Hall of Fame for dating a long list of utterly beautiful women. John Mayer has released numerous popular albums, including Heavier Things, Try, and Continumm. He won a Grammy Award for the single “Your Body is a Wonderland.” At one point, he went from being a reclusive artist rarely seen in public to one of the most controversial celebrities. It was during this time that he dated numerous beautiful celebs.

John Mayer has dated several famous actress, including Jennifer Love-Hewitt, Minka Kelly, and Jennifer Aniston. He was involved in two fairly high profile relationships with fellow musicians. John Mayer briefly dated pop singer Katy Perry. He later dated Grammy Award-winning artist Taylor Swift. They never officially confirmed their relationship until after they broke up when Swift released the song “Dear John.”

3 Jennifer Lopez


Jennifer Lopez is one of the most legendary players in Hollywood. She’s even played players, leaving them devastated and heartbroken. She has released several memorable albums, including On The 6, J. Lo, and Como Ama una Mujer. She has also starred in the films Selena, Out of Sight, and Monster-in-Law.

From 1999 to 2001, she was in a relationship with rapper and producer Sean “Puff Daddy” Combs. In 2001, she married her back up dancer, Chris Judd, but they both got divorced in 2003. She then became apart of one of the most talked about celebrity couples of all time. In 2002, she dated actor Ben Affleck in a highly publicized relationship. They split up the day before they were going to get married. In 2004, she married Marc Anthony and had twins together before divorcing in 2011. From 2011 to 2014, she dated former backup dancer Casper Smart. She is currently dating former New York Yankee Alex Rodriguez. She has also been rumored to have been involved with actors Bradley Cooper, Rodrigo Santoro, and musician Drake.

2 Leonardo DiCaprio


Leonardo DiCaprio is an Oscar-winning actor, environmentalist, owner of an island, and an intense serial dater. He’s been with as many women as the movies he’s been in. Leonardo DiCaprio is best known for his role in the critically acclaimed blockbuster Titanic. Additionally, he’s starred in numerous highly praised films, such as The Departed, The Wolf of Wall Street, and The Revenant.

Leo appears to really enjoy spending time with models. From 2000 to 2005, he dated model Gisele Bundchen. From 2005 to 2010, he dated model Bar Refaeli. In 2011, rumors swirled that he was dating actress Blake Lively but it was never confirmed. From 2011 to 2012, he dated model Erin Heatherton. In 2015, rumors suggested that Leo was then dating singer Rihanna. In 2016, he began dating model Nina Agdal. Additionally, he was rumored to be dating Katie Cleary, Miranda Kerr, Kidada Jones, and Paris Hilton.

1 Taylor Swift

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The most legendary players throughout history and the world are in awe of who is arguably the greatest player of all time—Taylor Swift. Swift has released several renowned acclaimed albums, including Taylor Swift, Fearless, Speak Now, Red, and 1989. She has won 10 Grammy Awards and holds 5 Guinness World records. One of those records should include breaking more hearts than anyone else.

In 2008, she began dating fellow musician Joe Jonas. Later, she dated another musician and fellow player, John Mayer. In 2010, she moved from musicians to actors and began dating Jake Gyllenhaal. She went on to date several other actors, including Cory Monteith, Toby Hemingway, and Taylor Lautner. From 2012 to 2013, she returned to musicians and dated Harry Styles. She has also been linked to Conor Kennedy, Tim Tebow, Garrett Hedlund, Patrick Schwarzenegger, and was said to have been dating Tom Hiddleston. Taylor Swift is certainly a first ballot for the Player’s Hall of Fame.

Sources: styleblazer

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