Leonardo DiCaprio: The complete hookup history

Douglas Charles Managing Editor

In our continuing series taking a look at some of most legendary ladies men, today we will discuss the alleged sexual history of Leonardo DiCaprio. The man who was once in charge of “The Pussy Posse.” Derek Jeter’s sexual history is impressive, Wilder Valderrama’s is mind-boggling, but neither of them hold a candle to Leo. There’s a reason he’s 37 and never been married. With a list like this, would you get married?

Note: There are so many we’re just going to combine years with a few in the interest of brevity.

Brittany Daniel, Bridget Hall, Naomi Campbell (1994-1995)

A hot actress and two supermodels, Leo was just getting started. Mind you he was 19 in 1994.

Claire Danes & Kristen Zang (1995-1997)

Leo is firmly establishing his M.O. of only dating hot actresses and models. He’s turns 21 during this time frame.

Kate Winslet, Linnea Dietrichson, Helena Christensen (1997)

Leo now has Titanic under his belt, giving him even more ammunition, and he uses it wisely.

Bijou Phillips, Amber Valletta, Eva Herzigova (1998)

1998 was a very good year. He really was King of the World!

Gisele Bundchen (2000-2005)

Breaking his pattern it was just one woman for Leo now, but it was the highest paid model in the world.

Trishelle Cannatella (2002)

Whoops, did we say just one woman? Well, she was on The Real World, a Playboy model and a future Lingerie Football League player, so…

Sienna Miller (2005)

Leo, being the savvy guy that he is, briefly took advantage of Sienna and Jude Law’s relationship issues.

Bar Refaeli (2006-2011)

Here’s the one that we thought would stick. And it did for a long time, but we should have known better.

Ashley Roberts & Anne Vyalitsyna (2009)

Bar and Leo had some issues. (Note the date.)

Blake Lively & Alyce Crawford (2011)

He moved on nicely though.

Kendal Schuler & Madalina Ghenea (2011)

Did I mention he moved on nicely?

Erin Heatherton (2011-Present)

Leo’s 2011 was better than 99.9999% of every man in the world’s entire lifetime with regard to dating women. I’d strut too if I was him.

Other less-substantiated alleged flings…

Hold on… it’s quite a list…

Bobbie Brown, Emma Bunton, Karen Butler, Mariah Carey, Carmen Electra, Heather Graham, Monica Hansen, Vanessa Hayden, Natasha Henstridge, Lauren Holly, Rachel Hunter, Sara Foster, Paris Hilton, Kendra Jade, Kidada Jones, Carmen Kass, Virginie Ledoyen, Juliette Lewis, Lindsay Lohan, Demi Moore, Kate Moss, Carla Paneka, Tawney Sablan, Ashley Scott, Alicia Silverstone, Jessica Simpson, Alyssa Sourovoya, Vanessa Trump, and Liv Tyler, phew!

Photo credit: YouTube/Warner Bros.

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