Leonardo DiCaprio is one of Hollywood’s most adored actors. Nominated for an Oscar at the ripe age of 19 for his performance in What’s Eating Gilbert Grape, Leo was bound for super stardom. But, DiCaprio isn’t only known for his stellar acting career. A lot of people also know Leonardo to be one of Hollywood’s most swinging bachelors.
Over the years DiCaprio has dated a literal “who’s who” of Hollywood’s hottest. From supermodels to movie stars, Leo has dated them all. Leonardo is the immaculate mack: charming, interesting, a bit mysterious. He’s every girl’s dream. In his spare time, Leo likes to hang out on yachts, take in basketball games and, of course, mingle with extremely gorgeous women.
At the beginning of this past summer a new trend emerged: the ill-fated “dadbod”. Every “dadbod” article seemed to use the same photo to legitimize the trend. It was Leo, admittedly looking a little chunky, hanging out on the beach. The thing is, there was no real “dadbod” trend (being out of shape is never en vogue). Leo can pull off being out of shape, Joe Six-pack (or rather Joe Kegstand) cannot. This is Leo’s magnetic power; he can do anything and gorgeous women will still be uncontrollably attracted to him. Check out a list of some of Leo’s hottest lady friends below.
15. Giselle Bundchen
Before Giselle Bunchen married Tom Brady she is said to have been in an on and off relationship with Leo from 2000-2005. Giselle is a Brazilian supermodel and former Victoria’s Secret Angel who in 2014 was ranked the world’s 89th most powerful woman by Forbes.
Considered by some to be the only true supermodel remaining, Giselle is currently the highest paid model in the world. In addition to modeling, Giselle is also an active philanthropist. She’s done quite alright for herself following her relationship with Leo.
14. Blake Lively
Although never officially confirmed, Leo and the absolutely gorgeous Blake Lively were spotted in a variety of local bars and clubs in 2011. Apparently the relationship fizzled (much like Lively’s career).
After a promising start to her career, beginning with her standout role in The Sisterhood of the Traveling Pants, Blake’s career has seemed to stalled after her falling out with Leo. Perhaps her role in an upcoming untitled Woody Allen project will help revitalize her career. But I wouldn’t be too worried if I were her, she is married to Ryan Reynolds, who is a rising star in Hollywood.
13. Miranda Kerr
DiCaprio was spotted out and about with Miranda Kerr in 2013. No surprise here as DiCaprio has a thing for rising stars like Kerr. Kerr is widely known for her work as a Victoria’s Secret Angel as well as a variety of other modeling work. She has also served as the face of H&M clothing (replacing Giselle Bundchen) and a model for Reebok and Wonderbra.
The Australian beauty is also a writer and owner of a cosmetics line called KORA Organics. Men’s Health magazine named Kerr one of the “100 Hottest Women of All-Time.” She was also named the “Sexiest Woman Alive 2012” by Esquire UK.
12. Bar Rafaeli
Leo and Bar Rafaeli had an on-and-off relationship for a handful of years during the early 2000s. This is one of his more “serious” past relationship, a relationship that had many people buzzing about whether Bar was the woman who would finally get Leo to settle down. Bar Rafaeli is one of the world’s most indemand models having been voted number 1 in Maxim magazine’s Hot 100 List of 2013.
The Israeli-born beauty has modeled for a wide variety of brands, including Chanel, Gap and True Religion, among others. Bar was also the cover girl for 2009’s Sports Illustrated edition. In addition to her modeling work, Bar also hosts the Israeli edition of The X-Factor.
11. Naomi Campbell
According to reports, Naomi Campbell and DiCaprio dated briefly in 1995. It shouldn’t come off as much of a surprise since Campbell is no stranger to dating rich and powerful men, having also dated Mike Tyson and Robert De Niro. Quite the repertoire, Naomi!
Campbell is a famous English supermodel who has done a litany of high-powered modeling work (i.e. she was photographed by the great Annie Liebowitz for Vogue’s watershed Millennium Issue). In addition to her work as a model, Campbell is also credited as an author, actor and singer. She’s made headlines for all the wrong reasons lately, thanks to alleged substance abuse.
10. Helena Christensen
DiCaprio and Helena Christensen were briefly linked together. Christensen is a Danish model and beauty queen who has done work for Victoria’s Secret and covered Vogue, Elle and Harper’s Bazaar, among others.
Christensen was considered to be one of the original “Magnificent Seven” supermodels along with Cindy Crawford, Christy Turlington, Naomi Campbell, Claudia Schiffer, Linda Evangelista and Elle MacPherson. In addition to her modeling career, Christensen is also a huge supporter of breast cancer awareness campaigns. This is one model who sort of fell of the face of the Earth, so to speak.
9. Eva Herzigova
According to the supermodel, she and Leo had a brief one month tryst in 1998. The Czech model and actress has had a storied career, frequently modeling for both the Sports Illustrated Swimsuit Edition and the Victoria’s Secret catalogue. Again, no surprise here as Leo has a thing for Victoria’s Secret Angels.
Herzigova was also the subject of very high-profile ad campaigns for Guess Jeans and Wonderbra. The beauty has also starred in a Duran Duran music video and a variety of (mostly foreign) films and shorts.
8. Bijou Phillips
Bijou Phillips allegedly dated DiCaprio briefly in 1998. They’re just rumors, but considering Bijou has a variety of talents, like working as a model, actress and singer, it’s not outside the realm of possibility that she temporarily snatched up Leo.After gaining notoriety as a model, Phillips quickly moved into the acting realm, scoring stellar roles in Almost Famous and Bully.
Phillips is the daughter of John Phillips of the famed band The Mama’s and the Papa’s and she is married to former That 70’s Show star Danny Masterson. The two were married in an Irish castle in 2011. Both Phillips and Masterson are Scientologists.
Over the past year Rihanna and DiCaprio have been spotted together on a variety of occasions leading to many rumors about the two dating. Rihanna, originally from Barbados, is a pop singer whose first single “SOS” went to number one on the Billboard charts.
Her career has continued on the uptick as she has had numerous hit songs and a variety of awards (including eight grammies and 23 Billboard Music Awards). If the rumors are true, and Leo and Ri Ri are in fact dating, we could be looking at one of Hollywood’s hottest and most powerful couples.
6. Toni Garrn
Garrn and Leo were linked together from 2013 to 2014. Garrn is a gorgeous model of German descent who burst onto the fashion scene in 2008 after signing an exclusive modeling deal with Calvin Klein.
Garrn has also walked the runway, modeling for revered fashion houses like Dior, Chanel and Louis Vuitton to name a few. The break-up with Leo doesn’t seem to be affecting Toni too much as she is currently dating Dallas Mavericks’ forward Chandler Parsons.
5. Erin Heatherton
According to media reports, DiCaprio and Heatherton were in a relationship from 2011 to 2012. Heatherton is an American model of Jewish descent who was born and raised in the Chicago suburbs.
She is well known for her work for Victoria’s Secret but has also walked the runway for brands like Marc Jacobs, Dolce & Gabbana and Zac Posen. Aside from modeling, she has also made cameos on FX’s fantasy football-based comedy The League and in the Adam Sandler buddy comedy Grown Ups 2.
4. Claire Danes
After starring together in Baz Luhrmann’s Romeo and Juliet, both Claire Danes and DiCaprio are said to have had a brief romantic fling in 1995. Since starring alongside Romeo in the classic romantic-tragedy, Danes has continued acting, recently garnering widespread acclaim for her portrayal of bipolar CIA operative Carrie Mathison in Showtime’s hit series, Homeland.
In 2013, Danes won a Primetime Emmy for this portrayal. Even more recently, in 2015, Danes was awarded a star on Hollywood’s storied Walk of Fame.
3. Bridget Hall
In 1994, very early on in Leo’s career, he was often seen canoodling with the gorgeous, young Bridget Hall. Bridget who, you ask. She isn’t very popular, but we can see what Leo saw in this gorgeous blonde.
By the age of 10, Hall was discovered and became a model. By 17, she was considered by Forbes to be one of the world’s highest paid supermodels. Hall covered magazines like Elle, Vogue and Harper’s Bazaar while modeling in huge campaigns for the likes of Guess Jeans and Pepsi Cola.
2. Trishelle Cannatella
According to some reports, Leo was, at some point, linked to reality TV star Trishelle Cannatella. Readers may remember Trishelle from her original stint on television as part of the cast of The Real World: Las Vegas – you know, one of the first shows to lay the groundwork for reality TV.
Well after what was supposed to be her 15 minutes of fame, Trishelle went on to work on a variety of other reality shows (most notably The Surreal Life). She has also posed nude for Playboy and competed as a professional poker player, earning $20,000 after a third place finish in the WPT Invitational Tournament.
1. Kristen Zang
Zang and DiCaprio are said to have dated from 1995 to 1999. Seems like DiCaprio dated many women during this time frame. Zang was a successful model during the 90s and also had a brief acting career.
After a promising start to her career where she appeared in All My Friends Are Cowboys and Love & Sex, as well as made a brief cameo on the ABC sitcom Dharma & Greg, she has since only appeared in poorly-received low budget television series and movies. Zang is also said to have dated Nicolas Cage, Michael Hutchence of INXS and Constantine Maroulis. Quite the drop off from Leo I’d say.
- Ad Free Browsing
- Over 10,000 Videos!
- All in 1 Access
- Join For Free!