Hollywood's 10 Biggest Playboys

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

9 Sean Penn

8 John Mayer

7 Justin Timberlake

6 Wilmer Valderrama

5 Ryan Gosling

4 Bradley Cooper

3 Orlando Bloom

2 George Clooney

1 Leo DiCaprio

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.


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Hollywood's 10 Biggest Playboys