The only Oscar nomination Leonardo DiCaprio genuinely didn’t want to win: “I have a funny feeling”
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Fri 3 April 2026 18:15, UK
When Leonardo DiCaprio finally won the big one and claimed his coveted Academy Award for The Revenant, somebody had to step in and take his place as the Oscars’ new nearly-man.
The way things are going, it seems almost fitting that Timothée Chalamet looks to be in pole position to fill the gap vacated by DiCaprio crossing the last remaining hurdle of his career, even if the three-time loser, four if you count his ‘Best Picture’ nomination for producing Marty Supreme, is a lot more transparent in his desire to win.
Not quite as transparent as Bradley Cooper, though, who couldn’t make it any clearer that he really, really, really wants an Oscar of his own, but nobody is anywhere near as invested in his desperate quest for a statue as they are for Timmy’s, even if a lot of those people hope the latter continues coming up short.
Sixth time was the charm for DiCaprio, who’s added another two ‘Best Actor’ nods to the collection since sending the internet into meltdown when his name was finally read aloud in 2016, when Alejandro G Iñárritu’s survival story saw him finally collect those flowers that he’d been robbed of at least once before.
Will he ever win another one? Most likely, since he’s Leonardo DiCaprio, and almost everything he touches is a prestige picture. It won’t hit the same, since he’s already got his on display in the trophy cabinet, but since that one meme ended, a thousand more have taken its place.
His eight nominations in total have been separated by 32 years, which speaks to his longevity, dating all the way back to a teenage DiCaprio being recognised for his staggering performance in What’s Eating Gilbert Grape? It was his very first rodeo, but it was one he was happy to walk away from with nothing.
“I have a funny feeling about the Oscars,” he shared. “When I was nominated for What’s Eating Gilbert Grape?, I really didn’t want to win.” That doesn’t sound like him, or at least the online perception about his crazed quest for glory, but he had a very valid reason for not wanting to be an Oscar-winner at 19.
“I thought that would create such an expectation about me in people’s minds,” he theorised. “You know, if you’re not perfect in every film after that, then people say, ‘See? He was just lucky in that one role.’” It’s an interesting point, and one that’s supported by quite a lot of history when it comes to teenage winners.
Tatum O’Neal, Anna Paquin, and Patty Duke are the only actors under 20 to win Oscars, and you could easily say that Paper Moon, The Piano, and The Miracle Worker remained the pinnacle of their big-screen careers. Timothy Hutton was 20 when he won for Ordinary People, and he didn’t get up to much either, so DiCaprio is right in suggesting it could have potentially cut him off at the knees.
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