Leonardo DiCaprio walked away from a Disney lead at 16 for a riskier drama, a choice he still calls one of the proudest moves of his career.

Before he became an Oscar winner, Leonardo DiCaprio nearly played the teenage hero in the 1993 Halloween comedy Hocus Pocus. He met with director Kenny Ortega, then passed so he could take a harder part in What’s Eating Gilbert Grape?

Mental Floss reported that the offer came after DiCaprio’s theatrical film debut opposite Robert De Niro in This Boy’s Life. That performance drew attention. The studio wanted him to audition for Max Dennison, the mortal boy who tangles with three witches back from purgatory.

Omri Katz ultimately played Max. Bette Midler, Sarah Jessica Parker, and Kathy Najimy starred as the witches. The film opened in July 1993 as a summer release and took in less than $50 million worldwide. It later found a second life as a Halloween cult favorite.

He sat down with the director, and said no

DiCaprio did meet Ortega. They even shared a sandwich. Ortega later recalled how clear the young actor was about his plans.

Ortega described the meeting this way:

"He came in, and he was just amazing, so extraordinary and unique, he came and he was stressed. He said, 'I feel bad that I'm here because I can't do this, because I'm really focused on these other things,' and I said, 'Understandably.'"

The “other things” pointed to Lasse Hallström’s What’s Eating Gilbert Grape? Hallström had already earned an Oscar nomination for Best Director for My Life as a Dog. DiCaprio wanted the role of Arnie, a demanding part opposite Johnny Depp.

Money was on the table. He still walked.

The Disney job would have paid well for a teenager. DiCaprio later said the salary was “more money than I ever dreamed of.” He still refused it.

He has described the pressure around him at the time:

"I don't know where the h*** I got the nerve... You live in an environment where you're influenced by people telling you to make a lot of money and strike while the iron's hot."

At 16, he chose the project he found more artistically interesting. He has not softened on that call.

DiCaprio put it plainly years later:

"If there's one thing that I'm really proud of in my entire career, it's that moment at 16 to say that and do that and have that sort of conviction of what I wanted to do."

The harder role paid off

The Gilbert Grape performance earned DiCaprio his first Oscar nomination, for Best Supporting Actor. In 2015 he won Best Actor for The Revenant, directed by Alejandro González Iñárritu.

Katz kept the Hocus Pocus lead. The movie underperformed in theaters, then became a seasonal staple. Fresh interest still flares whenever audiences learn how close DiCaprio came to the part.

A 16-year-old turned down easy money and a studio showcase because the other script asked more of him. That kind of early discipline still separates lasting careers from short ones.