pinterest-p mail bubble share2 google-plus facebook twitter rss reddit linkedin2 stumbleupon
The Premium The Premium The Premium

Hollywood’s 10 Biggest Playboys

Most Popular
Hollywood’s 10 Biggest Playboys

via TheRichest

From famous off screen love to sneaky celebrity hook ups to quickie marriages, we reveal some of the biggest moments in celebrity dating history and discover which Hollywood males have scooped the best dating track records.

You would think Hollywood is such a big place but alas, it seems like everybody is dating everybody and some dates are placed on repeat. A Hollywood Player may not always have a distinct taste, personality or even a particular type of women unless it comes to Leo Di Caprio when the order of the day is A-List actresses and hot supermodels.

At the end of the day celebrities live hectic lifestyles and so just like us, dating can become complicated. Relationships are hard work and we can only imagine having to try navigating one around the paparazzi and better yet maintain it. Then again, celebs do have access to a great choice in excuses when it comes to breaking up. They have to travel for work, they endure long hours on set every day and the constant gaze of the paparazzi can keep anyone on their toes.

We reveal the Top 10 male celebs in Hollywood with the best dating track record from Leo DicCaprio to George Clooney, Bradley Cooper and more. Check it out…

10. Ben Affleck

shutterstock_97698470

First to make it onto the Top 10 list is none other than A list celebrity actor Ben Affleck. The new face of Batman has had quite a past when it comes to his dating history that includes strippers, gambling and a string of hot exes. He famously made the leap from Jennifer Lopez to Jennifer Garner but alas their marriage is now ending in divorce. Then again in Hollywood standards, 10 years of wedded bliss with three kids isn’t too bad going. Rumor has it he was caught hooking up with a lap dancer but there hasn’t been a threat of blackmail or a secret sex tape to surface just yet. It looks like the list of celebrity sex tapes is Affleck free. For now…

9. Sean Penn

shutterstock_288368558

Sean Penn is next on our list and he certainly has had his fair share of A-list celebrity wives including the likes of Madonna and Robin Wright. When it comes to Hollywood players Sean Penn isn’t the first name to spring to mind as he likes to keep things under the radar and away from the prying eyes of the press. However the American actor, filmmaker, and political activist has been married twice for almost 24 years and has dated the likes of Calu Rivero, Jewel Kilcher, Petra Nemcova, Scarlett Johansson, Natalie Portman and Charlize Theron. When it comes to veteran actor Sean Penn, he has done pretty well for himself in both the acting and dating department.

8. John Mayer

shutterstock_155152298

More often than not John Mayer has been referred to as the “quintessential douchebag” in Hollywood but the singer has no problem feeding the press with ammunition with his recent dating shenanigans. His guitar skills and smooth voice just fuel his fire as he leaves a string of broken hearts across the Hollywood boulevard. Does he even have a dating type? Well apparently not as he has dated everyone from Oscar nominated actresses to Grammy award winning singers and models. So far the crooner has dated a string of Hollywood hotties including Jennifer Aniston, Taylor Swift, Minka Kelly, Vanessa Carlton, Jennifer Love Hewitt, Jessica Simpson, Taylor Swift and most recently Katy Perry. See why it comes as no surprise that John Mayer has made the cut now?

7. Justin Timberlake

shutterstock_154355981

Is it so wrong to want to live in a world where Justin Timberlake and Britney Spears made it? After the boy band era and bad hair days, Justin moved on to become much cooler than he should have. We took a peek through Justin’s ex files to see the succession of broken hearts he’s left behind and they include the likes of Ashley Olsen, Olivia Wilde, Alyssa Milano, Scarlett Johansson and even Cameron Diaz. Alas, the actor and singer is now happily married to fellow actress Jessica Biel and they share a wonderful son together. Looks like Justin has turned his life around and is headed straight for marital bliss, good luck!

6. Wilmer Valderrama

shutterstock_222802555

He may be an American actor, singer, producer and television personality but Wilmer will always be best known for his role as Fez in the sitcom That ’70s Show and for the ridiculously hot list of exes he has managed to leave behind. Who knew he knew how to wine and dine the ladies? He has dated everyone from Disney stars to co-stars to Oscar winner actresses to pop divas. So far Wilmer has been linked to Lindsay Lohan, Jennifer Love Hewitt, Mandy Moore, Minka Kelly, Ashlee Simpson, Rihanna, Avril Lavigne and his on again off again love Demi Lovato.

5. Ryan Gosling

shutterstock_91184072

Let’s face it: Ryan Gosling was always one of the most sought after men on the planet and after The Notebook aired it was just game over. Like art imitating life he developed a real life relationship with his on-screen love Rachel McAdams but his soulful eyes and smooth lines weren’t enough. Soon that fizzled but not before Ryan became an internet meme and viral sensation. Gosling went on to dabble in Cougarville with Sandra Bullock when he was just 21 and she 37 and then again with Famke Janssen enjoying a 16 year age gap. He finally set his sights on gorgeous Latina beauty Eva Mendes who is only 6 years his senior and they now share a child.

4. Bradley Cooper

shutterstock_383785639

It’s no secret that when it comes to dating, Bradley Cooper is never lacking female attention. Guess it doesn’t hurt being named Sexiest Man Alive by People magazine. His penchant for blondes and string of flings ranks him fourth on the list. When it comes to matters of the heart he’s anything but shy and his public displays of affection have sold a tabloid or three. Our dear Mr. Cooper has been romantically linked to the likes of Zoe Saldana, Jennifer Lopez, Cameron Diaz, Jennifer Aniston, Renee Zellweger, and even Jennifer Esposito. It seems when it comes to Bradley Cooper brunettes are the exception.

3. Orlando Bloom

shutterstock_129586886

Next on the ranking is Orlando Bloom. The Hollywood actor has come a long way since his days on The Lord of the Rings and Pirates of the Caribbean. Despite being more elf than actor he still managed to accrue a hot list of exes ranging from Victoria’s Secret models to Oscar winning actresses. It’s safe to say no one will ever have to describe any of Orlando’s ex-girlfriends with an awkward pause followed by a “but she has a great personality.” Orlando’s been linked to the likes of Kate Bosworth, Nina Dobrev and Selena Gomez. He was recently married to Miranda Kerr but ended the marriage after only three years.

2. George Clooney

shutterstock_277714805

People young and old swoon over him. Women want to date him and men want to be him. George Clooney’s dating type seems to be beautiful brunettes but then again blondes aren’t out of the question… His list of girlfriends over the years include Kelly Preston before she became Mrs. John Travolta of course, British model Lisa Snowdon, Parisian waitress Celine Balitran, Las Vegas cocktail waitress Sarah Larson, Michelle Pfeiffer’s sister Dedee Pfeiffer, Italian beauty and TV personality Elisabetta Canalis and most recently former WWE Diva Stacy Keibler.

1. Leo DiCaprio

shutterstock_290276477

Number one on the list has to be without a doubt Oscar winner Leo DiCaprio. His preferred dating type you ask? The supermodel of course. From Victoria’s Secret Angels to A-list actresses, Leo has dated the likes of Bar Refaeli, Blake Lively, Gisele Bundchen, Kelly Rohrbach and even Rihanna. Then again he would never limit his dating pool to just supermodels as he’s also been known to having dated Erin Heatherton, Amber Valletta, Helena Christensen and even Bridget Hall. When it comes to the best dating track record, Leo is unrivaled. When he’s not saving the environment and making Oscar winning movies, he dates professionally good looking blondes aged 25 or younger. Why? Because he can, making him one of Hollywood’s biggest playboys to date.

  • Ad Free Browsing
  • Over 10,000 Videos!
  • All in 1 Access
  • Join For Free!
GO PREMIUM WITH THERICHEST
Go Premium!

Videos