A then 19-year-old Leo was nominated for his role in What's Eating Gilbert Grape? Little did he know he'd be one of the most successful actors to date.
He also passed on starring in 1993's Hocus Pocus for the Gilbert role — good move, Leo!
"Things just happened so quickly. Out of nowhere a nomination came about and I remember being completely shocked. My Leonardo-DiCaprio-Whats-Eating-Gilbert-Grape-first-reaction was being terrified of ever having to go up onstage in front of a billion people," he said.
"Someone said 'a billion people watch this' and I thought, 'Oh my god, it's not like doing a movie where you get a second or third take'. Everyone's watching every word that you say. That was my initial reaction to it. It's a nerve-wracking thought."
Fun fact: He wouldn't be nominated again until 2005 for The Aviator — and he has yet to win. (Here's hoping he takes it home for The Wolf of Wall Street!)
Before the stars swarm the red carpet on Sunday, take a trip down memory lane and see what your favorite nominees looked like at their very first Oscars!