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King Of The Pussy Posse: A Brief History Of Leo’s Girls
  • by Boss Hunting
  •    Apr 8th, 2016
  •     Comments
  •    42848 Views

Jesus Christ Leo, can you please give us a chance?

Fresh off the back of his well deserved Oscar’s win, we thought it was high time we rubbed in Leo’s success just a little bit more with a look back through his dating history. Needless to say, in between shooting epic films and campaigning to save the planet, the man does extremely well with the ladies Victoria’s Secret models.

1993: Kate Moss

Leo started off his supermodel binge in style, bedding one of the most well known models of all time in Kate Moss. The relationship was apparently casual and short lived, but he got it done nonetheless.

MAY ISSUE of @britishvogue available on Thursday. #KATEMOSS

A photo posted by Kate Moss Latest ⚡️ (@katemosslatest) on

1994: Bridget Hall

As a 19 year old, Leo bedded barely legal 16 year old model Bridget Hall – apparently breaking it off with her soon thereafter.

1994: Brittany Daniel

You might know her from White Chicks, Leo knows her from His Bed as a young whipper snapper.

The young days on #DawsonsCreek… Just before I booked #JoeDirt. Miss my #shorthair cut! #tbt

A photo posted by Brittany Daniel (@iambdaniel) on

1995: Naomi Campbell

One of the most recognisable supermodels of the 90’s, the two were rumoured to have had a fling in ’95 as both were hitting their straps career wise. (We don’t think he’s slept with DJ Khaled #major🔑)

https://www.instagram.com/p/BC4J65_I5nc

1996: Kristen Zang

His first proper girlfriend, the two dated for a year and DiCaprio took Zang to the premiere of Romeo & Juliet, so I guess you could say things were pretty serious.

@leonardodicaprio It was only a matter of time and im so happy to see you receive this honor xoxo #tbt #oscars

A photo posted by Emma Lou's Kitchen (@emmalouskitchen) on

1997: Helena Christensen

Leo supposedly hooked up with the 28 year old Danish bombshell/actress when he was a spritely 23. The pair were getting it on around the release of Titanic in 1997.

1997: Natasha Henstridge

Henstridge looked set to have a big career ahead of her after dating DiCaprio and starring in The Whole Nine Yards. Unfortunately her career went the opposite direction of Leo’s.

1997: Demi Moore

As she was winding up her marriage with Bruce Willis, it was reported that Moore was spending time with DiCaprio. Discussing acting no doubt (or her penchant for younger men).

A photo posted by Demi Moore (@_demimoore) on

1998: Amber Valletta

Valletta is known as an actress who has done a little bit of everything but just never quite made it. She did however, manage to make it into Leo’s black book.

https://www.instagram.com/p/BDWsEyhIAR2/

1998: Bijou Phillips

The two met partying with DiCaprio’s infamous ‘Pussy Posse’ and briefly dated before she dropped him for Elijah Wood. Interesting call Bijou.

Actress #BijouPhillips in #LarryClark's #Bully.

A photo posted by @roisdulinge on

1998: Eva Herzigova

It’s around this time that Leo hits a purple patch (which happens to have continued unblemished for 18 years), starting out with the original Wonderbra model, Czech Eva Herzigova.

https://www.instagram.com/p/7i31hvGS0T

2000: Gisele Bündchen

Gisele really needs no introduction. The two had a widely publicised five year on-again off-again relationship before she wifed up for one of the only men in the world who can compete with Leo in the dating game, Tom Brady.

Looking back at my #Oscar moment with #Leo and #Gisele dress @Dior what an amazing look this was!!

A photo posted by Inge Fonteyne (@ingefonteyne) on

2005: Bar Refaeli

Leo backed up one of his longest relationships with another one, seeing Israeli stunner and VS model Bar Refaeli for a number of years before realising that there were other models he had to see feel before he died. It would also appear Refaeli is now expecting her first child (not to Leo) – congrats!

https://www.instagram.com/p/BD8N_PtMUT4

2009: Anne Vyalitsyna

Leo took a break from the VS models when he briefly saw Sports Illustrated model Anne Vyalitsyna.

https://www.instagram.com/p/BDl-OfUhkmU

2009: Ashley Roberts

Leo bedded ex Pussycat Doll Roberts while on the rebound from Refaeli, an out of character digression from the model theme.

Rocking a bit of @philiparmstrongcom for #SaturdayNightTakeaway tonight. And nails by @nailsinc thx @sheppardstyle

A photo posted by Ashley Roberts (@iamashleyroberts) on

2011: Blake Lively

The two dated for about five months before parting ways. Ryan Reynolds quickly swooped in on Lively, one of the sexiest women alive.  Good move Ryan.

https://www.instagram.com/p/uQjRqDR4Fc

2011: Kendal Schuler

Moving on quickly from Lively, Leo turned his focus on Australian model Kendal Schuler, bloody good on him.

https://www.instagram.com/p/BAscmmCLjj6

2011: Mădălina Diana Ghenea

Adding to his list of countries ticked off, Leo briefly dated (for a few weeks) Romanian model Ghenea in 2011 while shooting The Great Gatsby.

#memories #onset #zoolander #owenwilson @zoolander

A photo posted by Madalina Diana Ghenea (@officialmadalinaghenea) on

2011: Erin Heatherton

Some of his finest work here. Leo and Erin were together for almost a year before they realised their schedules just wouldn’t work. Most of us would probably just adjust our schedules for Heatherton.

https://www.instagram.com/p/BD4A2kliPVT

2013: Barbara Palvin

It must get awkward when Leo’s name comes up down at the Victoria’s Secret runway. Another year another supermodel. Sigh.

https://www.instagram.com/p/BAqVwvgHARB

2013: Toni Garrn

And another one…

#tbt to being tan

A photo posted by TONI GARRN (@tonigarrn) on

2015: Kelly Rohrbach

You’ll be seeing Rohrbach in the upcoming Baywatch film, Leo has already seen plenty of her.

https://www.instagram.com/p/BDbJL8AENlG

2015: Rihanna

And to cap it all off, turns out Leo has been seeing RiRi on the side for the past few years as well. Damn son.

 

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