Once Upon a Time In Hollywood was Leonardo DiCaprio's 28th feature film role and one of his greatest. But what's his very best? In a career spanning nearly three decades, DiCaprio has risen from teen heartthrob to the biggest movie star on the planet. He's done it with bold, ambitious choices, few mistakes, and plenty of support. Still, he's the one most responsible. DiCaprio is a true acting talent — an everyman who can handle any genre (although not every accent). Let's take a look back at Leo's career, and reveal his greatest roles ever.(Editor's note: We're ranking movie roles here. No TV allowed.)