A brief history of the ultra famous women you probably forgot Leonardo DiCaprio dated.


Oh, Leo.

Hollywood heartthrob of the 1990s. Former demi-god plastered all over the bedroom walls of teenage girls (aka my wall). Actor who had to fight a bear to finally get his acting Oscar. Environmental warrior. And… founding father of the ‘Pussy Posse’.

Yes, Leo, that's you we're talking about. Image: Getty.

It's no secret that Leonardo DiCaprio's favourite hobby is partying on a yacht in the Caribbean with models. He and his crew, the aforementioned Pussy Posse, which included fellow stars Tobey Maguire and David Blaine, were known for prowling and bonking their way through the social scenes of New York and Los Angeles. And while in many ways Leo certainly matured, he kinda sorta never grew out of his philandering ways. (Oh, but he is campaigning against climate change so we can forgive any indiscretions.)


And so, over the years, 43-year-old Leo (aka the original f*ckboy) has left behind a rather long trail of famous women he's dated. It's not easy to keep track of them all. But lost amongst the 462,502 young blonde models, there are a few surprises. Here are some of stars he was linked to you may have either forgotten about, or completely missed at the time.

Naomi Campbell

naomi campbell
Naomi Campbell. Image: Getty.

Legend has it that one of Leo's first supermodel girlfriends was Naomi Campbell. The two were said to be dating in 1995 but it lasted for about three seconds. They decided they had more a friend vibe going. And to this day, they continue to be mates, saving tigers and photobombing rapper 50 cent.

Gisele Bündchen

Gisele Bundchen
Gisele Bündchen. Image: Instagram.

Former Victoria's Secret model Gisele Bündchen is now famously happily married to American football star Tom Brady, with whom she has two cute-as-a-button kids and a reality TV show. But before Brady, there was Leo. The pair had and on-and-off relationship for about six years from 1999. Gisele, 37, remains the only girlfriend Leo ever brought with him to an awards show. It was serious, you guys.

Blake Lively

Blake Lively. Image: Getty.

OK, this one ended almost as fast as it started. One moment we were happily watching Blake play Gossip Girl "it" girl Serena, the next she was canoodling on a boat with Leo in Cannes. They brought their romance all over the world but the fling ended after five months in October 2011. Leo got back into his models while Blake, 30, went onto meet Ryan Reynolds and lived happily ever after with the sweetest children the world ever did see. The end.



rihanna harpers bazaar shark cover
Rihanna. Image: Getty.

Okay this is a romance the world very much wanted to happen. Surely if anyone could tame the beast that is Leo, it would be Rihanna, right? The pair were rumoured to be dating in 2015 and then the rumours just... stuck. For about a year. Alas, it seems they were just hooking up every now and again, but nothing more. (If at all. Rumours, eh?)


Bijou Phillips

bijou phillips
Bijou Phillips. Image: Getty.

Bijou Phillips, the daughter of singer John Phillips, dated Leo back in 1998. He introduced her to director James Toback, landing her the starring role in film Black And White. When things ended with Leo, she moved onto actor Elijah Wood and later married That '70s Show's Danny Masterson in 2011.


Emma Bunton

emma bunton
Emma Bunton. Image: Getty.

Ooooooh boy. Leo may or may not have dated a Spice Girl. Baby Spice, to be precise. While you were singing "if you wanna be my lover" in 1997, your two '90s worlds collided, bringing Leo and the Spice Girls together. We don't have much more to work with here, because this alleged romance was never confirmed and the most Bunton, 42, has said about it was five years ago when she described the reports of the time as "strange", so you'll just have to use your imagination, folks.