From supermodels to actresses, there isn't a doubt that Leonardo DiCaprio has a way with his words. If you’re a girl, chances are you've probably gawked over Leonardo DiCaprio since his worldwide, life changing success Titanic, or perhaps even since his first movie to gain public appraisal, Basketball Diaries. Guys want to be him; girls want to be with him. From his flowing blond hair and blue eyes, to his proud stature and incredible acting talents, it isn't a surprise that Leo has captivated the hearts of millions of viewers throughout the past twenty years. At the same time, he’s been extensively working on an ever-growing list of supermodel, actress and simply gorgeous life partners. Tina Fey even hilariously called him out on his, ahem, lady-charming skills at last year’s Golden Globe awards by saying, “And now, like a supermodel’s vagina, let’s all give a warm welcome to Leonardo DiCaprio” (The actor merely laughed off this humorous attack as he continued thanking the people around him). Let’s see what beautiful women have been a part of this handsome modelizer’s life during the past decades!
10 Blake Lively
Blake Lively is known to most as the star of the hit TV series Gossip Girl. Every member of her family (including herself) is part of the acting profession. Aside from being an excellent student, Blake was also a cheerleader, class president and part of the school’s choir. Blake and Leo were spotted together during the summer of 2014, yachting in Cannes, walking through Portofino and bike riding in New York City. One of Leo’s friends told Us Weekly that “[he/she had] never seen him like this with a girl”, making everyone speculate that she might be the one. Blake even visited Leo in Australia while he was filming The Great Gatsby. After having spent five months together, the couple split and are said to have remained friends.
9 Toni Garrn
Toni Garrn, a beautiful twenty-two year old German model, first began hanging out with Leo in May 2013, and broke up after more than a year together. They were first linked together while partying with friends at a Grand Prix event in Monaco. Garrn has been associated to several brands and has worked with many designers, notably Calvin Klein, Victoria’s Secret, Vogue and Elle. Sources say that they had never walked a red carpet event together, and the breakup reportedly occurred after Leo was spotted exiting a Miami nightclub surrounded by twenty women, most of them models. Surprising?
8 Erin Heatherton
Erin Heatherton, standing tall at six feet, began dating Leo at the beginning of 2012. She was discovered during a family trip in Miami when she was still in school. During the following years, she began her career in New York City, working for reputable designers such as Diane Von Fürstenburg and then continuing for Blumarine, Dolce & Gabbana, Lacoste, Marc Jacobs, Micheal Kors and many more. Recently, she has been a recurring angel in Victoria’s Secret shows and is an aspiring actress. The couple reportedly broke up after ten months together because they were both simply really busy and had crazy schedules. Leo would spend months abroad filming. Sources say that they still remain close and care for each other.
7 Madalina Diana Ghenea
Madalina Diana Ghenea, best known for her actress and fashion model career, began working in Italy and became widely popularized in 2010. The Romanian beauty began acting very young, performing for a famous children TV show. When she was a mere age of fourteen, an Italian designer discovered her. Fluent in five languages, Madalina also embraces a political career, being an international activist. She and Leo dated in 2011, first spotted together in Sydney while Leo was filming The Great Gatsby. Following this, Madalina denied the relationship and insisted that they merely had mutual friends.
6 Bar Rafaeli
Bar Rafaeli, a stunning Israeli model, started modeling at the mere age of eight months old, being featured in commercials. She appeared in five editions of Sports Illustrated Swimsuit – in the 2009 edition she was featured on the front page. Bar and Leo spent many years together, on and off. They first met at a party hosted by U2 in Las Vegas. They first started dating from 2005 to 2007, broke up for around two months, and got back together from 2007 to 2011. When approached about the blossoming relationship between Leo and Rihanna, Bar gave her blessing, saying “I think Rihanna is amazing. She must be everyone’s type.”
5 Gisele Bundchen
Gisele, just like Leo, Madonna or Cher, is so big that she only needs one name to be recognized. Standing tall at 5’11”, she has adorned countless magazine covers such as Cosmopolitan, Vogue, Rolling Stone and Forbes, the last magazine having named her the best-paid model of all time. She has signed multi-million dollar contracts with several of the world’s largest companies, notably with Victoria’s Secret, Louis Vuitton and Dolce & Gabbana, to name a few. The recently retired Brazilian supermodel dated Leo for five years before they parted ways. People Magazine had even named them “The Most Beautiful Couple in the World” in 2004. The couple reportedly split because Gisele was fed up of waiting for Leo to pop the question after dating for years.
4 Eva Herzigova
The beautiful blonde Czechoslovakian bombshell is known for starring in the 1994 “Hello Boys!” modeling campaign for Wonderbra. In addition, she has been popularized for her acting and costume designing career. Back in 1998, Eva Herzigova and Leo dated after meeting at a movie premiere for The Man in the Iron Mask. Rumors say that their dating occurred while she was still married to Tico Torres, the drummer for Bon Jovi, and the relationship between her and Leo dissipated within a short month.
3 Kristen Zang
Kristen Zang, a model and actress, was discovered at the young age of fourteen. She spent her summers working in popular cities, and left her home of Michigan as she turned seventeen. It is said that Kristen and Leo dated on and off for more than a year, around the time that movies such as Titanic popularized Leo and brought him international recognition. It is even said that Leo would fly her to the Titanic set in Mexico while he was filming. Kristen was seen at Leo’s side for the 1997 premiere of his film Romeo & Juliet. Nearing the end of the Titanic filming, Kristen reportedly broke off the relationship because she foreshadowed Leo’s popularity and she didn't want the hassle of being in the limelight.
2 Helena Christensen
The Danish beauty always dreamed of being a musician, but instead had a break in modeling when she was still a child, at the mere age of nine. After having moved to Paris and competed in the Miss Universe contest, representing her country, she was discovered by a photographer in 1989. The half Danish, half Peruvian’s natural modeling flair struck him. She even had a break in acting in 1992, when she starred in the movie Inferno. Leo and Helena were first associated together around the same time his worldwide hit Titanic was released. The relationship was never officially confirmed, but they were linked together for a brief period in 1997.
1 Naomi Campbell
Naomi Campbell, a revolutionary model having posed for the cover of Vogue at the tender age of eighteen, was indeed the first black woman to appear on the cover of this French magazine. After that, the supermodel also appeared as the first black woman on the covers of British Vogue, as well as Time. The leggy British beauty actually appeared in Bob Marley’s music videos before starting to pose for a modeling agency at the age of fifteen. Leo and Naomi had a brief fling in 1995, but mutually decided that they would remain friends, which is still the case today. Just recently, they were spotted yachting together!