By Melissa Locker
Updated January 16, 2014 11:00 AM

Leonardo DiCaprio received his fourth Oscar nomination Thursday, for his portrayal of seedy stockbroker Jordan Belfort in Martin Scorsese’s The Wolf of Wall Street.

DiCaprio is no newcomer when it comes to the Academy Awards, though. Twenty years ago, he made his Oscar debut when he was nominated for Best Supporting Actor for his work in 1993’s What’s Eating Gilbert Grape?

DiCaprio starred alongside Johnny Depp in the drama, directed by Lasse Hallström. Depp played Gilbert, a teen tasked with keeping his family together as he cares for his morbidly obese mother and his developmentally disabled little brother Arnie (DiCaprio). His responsibilities become onerous when he meets Becky (Juliette Lewis) and sees a chance for love.

The film was DiCaprio’s breakout role after his big-screen debut in Critters 3 and a role on beloved ’80s sitcom Growing Pains. Even though he was only 19 years old, his portrayal of Arnie was sensitive, complex and full of depth, belying his age, so there was no surprise when he was nominated for Best Supporting Actor for the part.

While DiCaprio didn’t take home the Oscar that night, it helped set him along the path to three more nominations, including nods for his roles in The Aviator, Blood Diamond and, now, The Wolf of Wall Street.

Watch him in the trailer for What’s Eating Gilbert Grape?:

And in The Wolf of Wall Street:

Can’t get enough of Red Carpet Season? Be one of the first to get the news from all the awards shows! Sign up below for our daily newsletter – so you’ll be the first to know all about the winners, the best speeches and the most fabulous fashion.

Like us on Facebook for more stories like this!