Leonardo DiCaprio’s Relentless Pursuit of His Own Masterpiece

Back in 2016, social media was flooded with jokes about Leonardo DiCaprio’s elusive Oscar. Punters couldn’t wrap their heads around the fact that, despite a string of standout roles—think What’s Eating Gilbert Grape and Shutter Island—he’d never nabbed the golden statue. It wasn’t until his gritty turn as Hugh Glass in The Revenant that he finally got his hands on one, putting an end to years of memes and online banter. As one person quipped, “RIP Leo’s Oscars meme.”

For DiCaprio, that so-called impossible dream was eventually ticked off the list. But by the time it happened, he’d already learnt to let go of the outcome, focusing instead on the work itself.

“It’s never ever what I’m thinking about when I’m making films,”

he once explained.

“There’s nothing I’ve done for the specific reason of getting an award. Every single time, you just go in there trying to bat a thousand, trying to give it your all.”

Chasing Recognition and Something More

DiCaprio has admitted that, like anyone, he’s not immune to the lure of recognition.

“I wouldn’t be human”

if he didn’t think about winning awards, he’s said. Still, the real motivation for him lies elsewhere—beyond trophies and applause. What keeps him coming back is the search for something less tangible, something that makes the whole gig worthwhile.

He’s always had his sights set on creating a true magnum opus. During promo for Clint Eastwood’s J Edgar in 2012, he told Back Stage:

“With every role that I’ve chosen or every film I’ve been a part of, I always think about the unbelievable accomplishments of actors and directors in the past and how many great performances have been given, and how many great films there have been in cinema’s history. And I have a great amount of respect for that.”

He went on,

“I suppose my endless, unattainable goal is to do something that is as good as I see in cinema’s past. And I don’t know if I will ever, on a personal level, believe that I have accomplished that. I don’t know if I’ll ever sit here and see a film and say, ‘This is absolutely everything I ever dreamed of on a personal or cinematic level.’ But that’s what sort of drives me.”

Looking Back and Moving Forward

Since those comments, DiCaprio’s filmography has only grown, with roles in The Great Gatsby, The Wolf of Wall Street, Killers of the Flower Moon, and, of course, The Revenant. Any of these could be considered career-defining by most standards. From the audience’s point of view, his peak might even be found in earlier hits like Catch Me If You Can, The Beach, Romeo + Juliet, The Aviator, or the ever-iconic Titanic.

But for DiCaprio, that sense of having truly nailed it remains out of reach. It’s a feeling shared by plenty of actors, especially those who’ve been at it as long as he has. When you hold the classics in such high regard, seeing them as the gold standard, it’s tough to ever reckon your own work measures up.