Leonardo DiCaprio can get pretty much any woman he wants, and during some points in his life, it seemed as though he was trying to get them all. Despite a few long relationships and the ability to keep most of those flings under wraps, Leo is still quite the Hollywood playboy with an affinity for mostly models — but sometimes actresses — and almost always blondes. It's quite a list, so let's take a stroll down memory lane and revisit some of his former flames…
RELATED: All the stars John Mayer has dated
Juliette Lewis, 1993
In the first of many on-set hookups, Leonardo DiCaprio dated his "What's Eating Gilbert Grape" co-star Juliette Lewis. She's got Brad Pitt on her dating resume, so this was a good early score for Leo and a sign of grape, er, great things to come.
Bridget Hall, 1994
Years after Leonardo DiCaprio's reported 1994 fling with Bridget Hall, The Sun ran a story claiming the actor took the model's virginity in London's Royalton Hotel — and alleged that she wasn't too thrilled with the experience. Bridget denied the whole thing and Leo has said that their relationship was "blown out of proportion," which is basically his way of avoiding any drama. Next!
Brittany Daniel, 1994-95
Brittany Daniel and twin sister Cynthia Daniel played the "Sweet Valley High" sisters on the '90s television series, but it was Brittany who played a little one-on-one with Leonardo DiCaprio when the two filmed "The Basketball Diaries" together.
Emma Bunton, 1998
You're nothing in Hollywood until you've dated a Spice Girl, and Leonardo DiCaprio's favorite flavor was Baby Spice. Emma Bunton was a young 20-something back then and the blondest of the bunch, so this hookup totally makes sense. She's been with her partner Jade Jones for more than 18 years now and they have kids together, so we don't think she's still carrying a torch for good ol' Leo.
Claire Danes, 1995-96
Once again, on-screen steaminess led to off-set lovin' for Leonardo DiCaprio, who reportedly hooked up with Claire Danes while they were filming "Romeo + Juliet." This relationship rumor feels more hopeful than anything, since fans of the film always want a storybook romance. But they spent enough time together that it's hard to believe there wasn't a little something off-set.
Kristen Zang, 1996-97
In 1996, Leonardo DiCaprio showed up to the "Romeo + Juliet" premiere arm-in-arm with model Kristen Zang. Take that, Claire Danes! Kristen's dad blabbed to the press about a private Thai island Leo'd taken her to while filming "The Beach," but she supposedly didn't like his friends (you know, the "posse"), so it wasn't long before that 15-month romance died down.
Alicia Silverstone, 1997
During Leonardo DiCaprio's wild times in the late '90s, he allegedly had a wandering eye that Kristen Zang didn't appreciate. As soon as they were done, Leo focused his attention on Alicia Silverstone, who was in her prime and busy being on FHM's hottest women list year after year. She was also coming off her "Batman & Robin" role, so the timing was right for a short-lived relationship between two of Hollywood's most beautiful and in-demand people.
Natasha Henstridge, 1997-98
Once that big boat went down (we're talking about "Titanic," people), Leonardo DiCaprio rode the wave of success into the arms of a number of women in 1997 and 1998. It was a streak of record proportions that should land him in some sort of dating hall of fame. He was also tied to one-nighters with Helena Christensen and Amber Valletta, but "Species" star Natasha Henstridge gets her picture up because rumors swirled that Leo had fathered her child — until she came out and revealed Liam Waite was the baby daddy.
Kidada Jones, 1998
Kidada Jones, the daughter of music mogul Quincy Jones (and sister of Rashida) and actress Peggy Lipton, famously dated Tupac Shakur. But in September of 1998, rumors were flying that she was at the center of a love triangle between Diddy (or Puffy or whatever he was calling himself back then) and Leonardo DiCaprio, who was still riding high on his "Titanic" fame. While it sounds fun, it wasn't long before the ship sank on the Kidada relationship.
Eva Herzigova, 1998
Leonardo DiCaprio was romantically linked to Czechoslovakian model Eva Herzigova after they were seen laughing and dancing together at the London premiere of his film "The Man in the Iron Mask." She was married to Bon Jovi drummer Tico Torres at the time — their marriage would end just a few months later. But despite reports claiming she dated Leo for about a month, Eva later insisted he was just an old friend. "He's a great guy but we never had an affair," she told The Mirror.
Naomi Campbell, one night in 1998
In March of 1998, the New York Post reported that Leonardo DiCaprio and Naomi Campbell were doing some "heavy-duty canoodling" in Paris, which is magazine code for getting it on. No matter what happened that night, the two did some serious yachting together in Sardinia in 2010… with their respective new significant others at the time, Bar Refaeli and Russian billionaire Vladimir Doronin.
Bijou Phillips, late '90s
The daughter of The Mamas & the Pappas leader John Phillips and singer Michelle Phillips, Bijou Phillips was a wild child back in the day. All that sex, drugs and rock 'n' roll cred won over Leonardo DiCaprio in the mid-'90s, when he reportedly saw her dancing at Bowery Bar, called writer/director James Toback, and got her role in "Black and White." Years later, they dated.
Gisele Bundchen, 2000-05
It seems like forever ago now, but before she was Mrs. Tom Brady, Gisele Bundchen was the stunning model who was able to tame Leonardo DiCaprio. They hit red carpets and went on public outings together and were the "It" couple during their run. In 2005, they were cursed by being added to People's "Most Beautiful Couples" list, which preceded their demise.
Demi Moore, 1998 & 2002
This one is more of a rumor than anything, but if it's on the Internet, then we like to believe it. The story is that Demi Moore cheated on Bruce Willis for one night with Leonardo DiCaprio in 1998 and then hooked up with him again in 2002 when she was single and he was on a break with Gisele Bundchen.
Sienna Miller, 2005
Leonardo DiCaprio and Gisele Bundchen were going through hard times and nearing the end of their romance when The Sun reported that Leo was cozying up to Sienna Miller at Los Angeles' Mood Nightclub. That supposedly ended the Gisele relationship for good. Sienna was on a break from Jude Law at the time, but her night with Leo certainly didn't end that relationship.
Sara Foster, 2002
Sara Foster is now married to tennis star Tommy Haas, but back when Leonardo DiCaprio was on a break with Gisele Bundchen, he scored with the former "90210" star. He even took her to dinner at Mastro's Steakhouse in Beverly Hills with former President Bill Clinton.
Bar Refaeli, 2006-11
Bar Refaeli was practically unknown when Leonardo DiCaprio started dating her, so he can take some credit for upping the Israeli model's profile. They were on-again, off-again for close to five years and secretly, we always wished they'd end up together. Bar has since gone on to marry Israeli businessman Adi Ezra. The two welcomed a daughter together in 2016.
Emma Miller, 2009
On a break from Bar Refaeli in 2009, Leonardo DiCaprio hit the London club scene with Emma Miller, who used to date actor Jesse Metcalfe. It was a big upgrade for her, but her stint on the A-list only lasted a few weeks at best.
Anne Vyalitsyna, 2009
Victoria's Secret model Anne Vyalitsyna spent a fun few days with Leonardo DiCaprio in Ibiza in 2009. He was on a break with Bar Refaeli and Anne V was single. Things didn't work out romantically with Anne and Leo, but Anne's career started to take off not long after. She later famously dated another notorious playboy: Maroon 5's Adam Levine.
Paris Hilton, 2010
Big star or not, you can't spend your life in Hollywood without being linked to a Hilton. In the summer of 2010, Paris Hilton and Leonardo DiCaprio were spotted together in Las Vegas and then again in Johannesburg watching the World Cup. It was just enough to get the gossip columns riled up for the release of "Inception."
Blake Lively, 2011
It was a little surprising when Leonardo DiCaprio started dating Blake Lively after his breakup with Bar Refaeli became official. She's a big star and all, but thanks to her run on "Gossip Girl," she was a tabloid darling, which isn't really Leo's style. (Then again, she is a tall, beautiful blonde — just his type.) They hit up the Grand Prix in Monaco and partied on the French Riviera, so it was a fun ride for the few months it lasted.
Alyce Crawford, 2011
While Leonardo DiCaprio was filming "The Great Gatsby" in Australia, he was "friendly" with the locals. Alyce Crawford, a former contestant on "Australia's Next Top Model," was identified by People magazine as a likely recipient of Leo's affections. Aussie model Kendal Schuler was as well. (No pic available, but surprise! She's beautiful.)
Erin Heatherton, 2012
Leonardo DiCpario enjoyed a 10-month romance with Victoria's Secret model Erin Heatherton in 2012. Although it was short-lived, both claimed to have parted amicably and cited busy schedules for the reason their relationship didn't work out. On to the next!
Toni Garrn, 2013-14
Leonardo DiCaprio and Victoria's Secret model Toni Garrn were spotted arriving on a yacht after watching the Monaco Formula 1 Grand Prix in May 2013. It was one of the first sightings of the pair, who spent that summer traveling together across Europe — from France to Ibiza. However, by 2014, they were dunzo after she reportedly got upset when Leo left a Miami hotspot with 20 young ladies. That'll do it!
Leonardo DiCaprio took a break from the models and was linked to Rihanna in early 2015. A report in TMZ said the two got "super-steamy and even swapping spit" at a party on Jan. 10, 2015 at the famed Playboy Mansion. Later, they ended up at the same afterparty where the website said, "things got even hotter." A year later, there were reports that they hooked up again in Paris.
Kelly Rohrbach, 2015
Kelly Rohrbach spent the summer of 2015 on the arm of Leonardo DiCaprio. But by the end of November of that year, their romance had fizzled. "It was mutual," a source told Us Weekly at the time. "They both have intense work schedules and a lot going on in their lives right now."
Nina Agdal, 2014 & 2016
Nina Agdal and Leonardo DiCaprio were first linked in 2014, but they rekindled the flame at the 2016 Cannes Film Festival. After that, they were seen in New York City, The Hamptons, Malibu, French Polynesia and St. Barts. In May 2017, though, it was reported that the duo had called it quits after a year together (the second time around).
Lorena Rae, 2017
Lorena Rae and Leonardo DiCaprio were first spotted out and about in July 2017, sources told People. The actor and the German model were seen on multiple dates throughout the summer and early fall before Leo was rumored to be pursuing a new beauty…
Juliette Perkins, 2017
Leonardo DiCaprio was most recently linked to 19-year-old model Juliette Perkins. The pair was spotted leaving a Los Angeles nightclub together in October 2017.