Honestly, it felt like the entire internet was holding its breath for about a decade. If you were online at all between 2010 and 2016, you probably saw the memes. Leo running away from an Oscar. Leo crying at the podium. The "Poor Leo" narrative was a staple of pop culture. But yes, Leonardo DiCaprio has won an Academy Award, and he did it in a way that basically forced the Academy to pay attention.
The win finally happened in 2016 at the 88th Academy Awards. He took home the statuette for Best Actor for his role as Hugh Glass in The Revenant.
It wasn't just a win; it was an event. By the time he walked onto that stage, he had been nominated for acting five times previously, dating all the way back to when he was a teenager. People weren't just happy for him; they were relieved. It felt like a collective "finally" from everyone who had watched him get snubbed for years.
The Performance That Broke the Curse
You've probably heard the stories about what he went through for The Revenant. This wasn't just acting; it was survival. Director Alejandro G. Iñárritu is known for being... let's say "thorough." DiCaprio didn't just stand in front of a green screen. He actually ate a raw slab of bison liver. He slept in animal carcasses. He spent a massive chunk of the film submerged in freezing rivers or crawling through the mud while suffering from actual hypothermia.
Basically, he made it impossible for the Academy to say no.
Critics often joke that the Oscars love "most" acting over "best" acting. They love seeing the physical toll. Since Leo had already given masterclasses in nuance in films like The Aviator and The Wolf of Wall Street without winning, he seemingly decided to go the route of pure, unadulterated physical suffering. It worked.
The competition that year was stiff—he was up against Bryan Cranston, Matt Damon, Michael Fassbender, and Eddie Redmayne—but the "Leo's Year" momentum was an unstoppable freight train.
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A History of Near Misses
Before the big win, DiCaprio’s relationship with the Oscars was a long string of "almosts." His first nomination came when he was just 19 for What's Eating Gilbert Grape (1993). He played Arnie Grape, and he was so convincing that many people who saw the film thought the producers had actually cast a boy with a developmental disability.
He lost to Tommy Lee Jones for The Fugitive. Fair, but tough.
Then came the Titanic snub. The movie won literally everything else—11 Oscars in total—but Leo wasn't even nominated for Best Actor. That started the conversation. Was he too much of a "pretty boy" for the Academy to take seriously?
The Full Nomination Breakdown
If you look at the stats, his track record is actually insane. Most actors would kill for one nomination; he has seven (six for acting, one for producing).
- 1994: Best Supporting Actor (What's Eating Gilbert Grape) - Lost
- 2005: Best Actor (The Aviator) - Lost to Jamie Foxx for Ray.
- 2007: Best Actor (Blood Diamond) - Lost to Forest Whitaker for The Last King of Scotland.
- 2014: Best Actor (The Wolf of Wall Street) - Lost to Matthew McConaughey for Dallas Buyers Club.
- 2014: Best Picture (The Wolf of Wall Street, as producer) - Lost to 12 Years a Slave.
- 2016: Best Actor (The Revenant) - WON.
- 2020: Best Actor (Once Upon a Time in Hollywood) - Lost to Joaquin Phoenix for Joker.
Many film buffs argue that his 2014 loss for The Wolf of Wall Street was the biggest robbery. His Jordan Belfort was high-energy, hilarious, and terrifyingly charismatic. But McConaughey had the "McConaissance" narrative and a massive physical transformation of his own. It’s kinda the way the Oscars work—it’s about the story as much as the performance.
Is He Still Chasing the Gold?
As of 2026, DiCaprio hasn't slowed down, and the Oscar buzz follows him like a shadow. He recently dominated the conversation with One Battle After Another, the latest Paul Thomas Anderson flick. People are already calling it a frontrunner for the 98th Academy Awards.
The interesting thing is that Leo doesn't seem to have that "desperate" energy anymore. Winning for The Revenant took the pressure off. He's arguably the last true "movie star" in the old-school sense—the kind of guy whose name on a poster guarantees a $100 million opening, regardless of whether it's a superhero movie or a three-hour historical drama.
He also uses his wins as a platform. Remember his 2016 speech? He barely talked about the movie. He spent almost the entire time talking about climate change.
"Climate change is real, it is happening right now. It is the most urgent threat facing our entire species, and we need to work collectively together and stop procrastinating."
It was a bold move, but when you've waited 22 years for a microphone, you're going to say what matters to you.
What's Next for Leo?
If you're keeping score at home, the quest for a second trophy is very much alive. With his frequent collaborator Martin Scorsese still active and his penchant for picking "prestige" scripts, it’s a matter of when, not if, he gets back to the podium.
For fans, the "has Leonardo DiCaprio won an academy award" question is settled, but the "will he win another" is the new debate.
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If you want to track his current standing in the 2026 race, keep an eye on the Critics' Choice and SAG results. Those are usually the best "weather vanes" for where the Academy is leaning. Right now, he’s a near-lock for a nomination for One Battle After Another, though he’s facing some heavy competition from younger stars like Timothée Chalamet.
The best way to appreciate his journey isn't just by looking at the trophy count. It’s by re-watching the roles that didn't win. Check out The Departed (where he wasn't even nominated despite being the best part of the movie) or Django Unchained. Those performances prove that while the Oscar is a nice piece of hardware, it’s the work that actually sticks around.
Next Steps for Film Fans:
Check out the 2026 Golden Globe winner lists to see how Leo's latest project performed; it’s the strongest indicator for the upcoming Oscars in March.