Leonardi DiCaprio paints on a different canvas — women (23 Photos)

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The list of the Leo’s girlfriends over the last 20 years.

Via Refinedguy

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  • GGLeo

    He's the Picasso of dating.

    • lukitas

      Leonardo DiCaprio and not Leonardi DiCaprio!!!!!!!

    • backseatchiver

      He keeps getting older, but they stay the same age.


      • Jack Wagon

        Madalena ghenea has a HUGE freaking mouth, that's what nightmares are made of. Unhinge her jaw and swallow you whole

        • Al W

          You and I must have a different definition of nightmare

    • humpire

      I want to see a George Clooney post. He might be able to compete

    • DiCaprio Want-A-Bee

      i am not worthy. I bow to Picasso!

    • Slim Jim

      i have a new hero

  • Tiber_Septim

    That's a lot of hot women to go through. dayum If you are going to date, date the best looking women in the world

  • TNchiver

    I hate you Leo.

    • Brandon
    • Captain Obvious

      Don't be jealous. I myself am satisfied with nailing fat wo- I can't even finish this its so sad.

    • Slim Jim

      he will be my inspiration when i pick up women at my nearest watering hole.

  • Chester

    Leo's a dirty slut.

    • nate33uc

      this dude went on an absolute tear from 2009 – 2012….to name a few, #16 #18 #20 #22…and that's only about half…way to go leo!

  • Chrissy

    A girl at work told me Bar rafaeli is now dating Shawn white………. Damn that is a brutal downgrade.

    • twd22285

      one lucky..dirty slut!

    • TJ82

      That is what's referred to as a "ripleys", as in "ripleys believe it or not"

  • Drew

    Leo is one of a handfull of people on earth who have modelitis. I sure would love to have that syndrome.

  • xXbeermonkeyXx

    #22 co-co-co-co-combobreaker from all the sweet blonde ass he was tapping

    • Cinurwe

      Dude, did you miss Naomi Campbell?

    • GnarShredder

      I prefer blondes, but hell, you can NOT pass her up.


      2011 was a good year

      • Superhcile

        Killer Instinct???

  • Jjo

    I thought he died when the titanic sank…

    • KFAD

      I actually just LOL'ed.

    • iRiv

      No, he was still alive when he washed up on shore in Inception.

    • Nigel

      You win at the Internet, Jjo. Bravo.

  • ladida

    pisses me off

  • innerV

    He even sneaked into my dreams to steal hot models from me…

  • http://www.youtube.com/watch?v=lHqSUoMEezw Christian

    A piece of #22 please!

  • hotrippr

    No matter how old he gets his girlfriends never age. Must be nice.

    • alex

      Looks like Leo took David Wooderson's logic to heart.

  • AstroMikeDexter

    I bet he went deeper.

    • Nigel

      And 100 Internet points to you for that reference.

  • Jon

    Wow probably impossible to top a list like that

    • guest847

      Probably tiger woods

    • Dan

      Jack Nicholson.

    • guest

      Unless you're George Clooney.

      • isitin

        Clooney is no where in the same league as Leo is.

      • matt

        im thinking jeters the only guy who coudl give him a run for his money

  • Chicago Sean

    #1 And she's preferred black guys ever since

    • Big Poppa

      isn't that Ryan Reynolds?

      • Dax

        got a good laugh from that, nice one.

    • B-Jammin

      She got tired of korny white guys

  • No wonder

    Year 2000 was the best year out of all. I also noticed that he constantly smiled. No wonder!

  • DChiver

    1998 seems to the busiest

  • Pete

    Look how Gisele lasted five years. I bet she is one hell of a good fuck

  • So interesting

    Seriously. We need to know if anyone has ever done better. Good post Chive and I hope to see more from this (new?) category :-)

    • JSt31

      Derek Jeter or Christiano Renaldo have impressive lists also

      • John

        Yeah I bet. Chive reading this? We want the lists

      • Gloryhound421

        Oddly enough a coworker and I were discussing this last week. He submitted Leo for best list, I counter with Justin Timberlake. Epic list of quality ass there.

        • Fuckedemall

          Clooney is the Master

    • guest

      or George Clooney.

  • JJL

    Close race between Bar and Heatherton for hottest on that prestigious list

  • ???

    So how many points do each get, Leo?

  • whyme1973

    Leo is one lucky sonofabitch.

  • https://www.facebook.com/thomas.radiguer Thomas Radiguer

    4 in 2011, that makes 3 months top each… I think Leo is not such a pleasant person to stay with :) #18 & #22 are the hottest imo :>

    • bigcityreem

      I agree with #22.

  • Seriously?!

    Once Leo tried black he never went back?
    Wtf !!??

    • mopmonkey

      Only applies if the black is that crazy b_tch Naomi Campbell

  • https://www.facebook.com/barend.pretorius Barend Pretorius

    He did good with an average of two a year to start of with had a slump in the middle 2000's but he seems to be back on form with a nice average again.

    • Tom

      Look who was ready for him in 2000. Yeah that's why

      • Craving

        G fucking Bundchen!

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