Leonardo DiCaprio has been mostly out of the spotlight since his lavish Summer spent traveling around the globe, but now he's back to making headlines for his over-the-top ways. Leo, who may have recently split from his model love Toni Garrn, reportedly left a Miami club with 20 girls while he was partying during the city's annual Art Basel event. He just turned 40 and has a seriously impressive résumé, and it's also obvious that he has had more than his fair share of girlfriends, admirers, and female friends. Take a look back at all of Leo's lovely lady friends — from ex-girlfriends Gisele Bündchen and Blake Lively to best pal Kate Winslet.
Leonardo DiCaprio and the Many Ladies in His Life
Around The Web
From Our Partners
Latest Celebrity & Entertainment