Inside the Untold Moments That Forged Leonardo DiCaprio’s Legendary Rise—Prepare to Be Shocked!

Can you believe it? Fifteen years have zipped by since Inception first twisted our minds and sneaked Leonardo DiCaprio even deeper into the Hollywood stratosphere. If you’re anything like me, that realization hits you like a surprise burpee mid-squat—unexpected and a little mind-boggling. It’s wild how this one film didn’t just boost Leo and Nolan’s careers but reshaped sci-fi storytelling altogether, planting seeds that sprouted into the multiverse mania we’re swimming in today. But beyond the layers of dreams and booming Hans Zimmer scores, there’s a fascinating journey of the man himself—Leo, the relentless actor who’s morphed from a fresh-faced heartthrob into a legend of the craft. With his latest flick, One Battle After Another, about to drop (and his first collaboration with Paul Thomas Anderson, no less), it feels like the perfect moment to sweat the details and celebrate five pivotal moments that made Leo, well, Leo. Ready to dive in? LEARN MORE

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Are you sitting down? You might want to grab a chair, because I almost passed out after reading that this year is Inception’s fifteenth anniversary. It’s not easy to make a guy in his early thirties like me feel he’s getting older [Editor’s note: Speak for yourself, Josh], but that one hit me right in the gut.

It’s no secret that Inception is an incredibly important film in the modern movie canon. Not just for the ascending careers of both Leonardo DiCaprio and Christopher Nolan, but for its impact on every brainy sci-fi concept film thereafter. We may have never suffered from our multiverse storytelling affliction if not for Inception’s journey through multiple layers of dreams. And without Hans Zimmer’s booming score, trailers that began with cheery narrators explaining exactly what the movie is about might not have gone the way of the dinosaurs. I’m not the kind of Nolan-obsessed Letterboxd bro to put Inception in my top four films, but it’s easily one of DiCaprio’s most iconic films.

The actor has a new movie out next month titled One Battle After Another. It’s his first with director Paul Thomas Anderson, who claims that the film full of car chases, guns, and high-energy camera work is his first true action flick. Of course, it wouldn’t be a P.T. Anderson joint if it wasn’t also about generational trauma. DiCaprio and Anderson discuss One Battle After Another in Esquire’s latest cover story, wherein the actor says that the inspiration came from how creatives of his age are “living in a completely different world than the next generation.” That disconnect is at the heart of their new movie, out in theaters on September 26.

So, in the spirit of Esquire’s cover story—and Inception’s fifteen-year anniversary—it felt right to look back on the five moments in Leonardo DiCaprio’s career that made him, well, Leonardo DiCaprio.

Romeo + Juliet (1996)

The world was largely introduced to DiCaprio as a child actor in What’s Eating Gilbert Grape (1993), but audiences didn’t fall in love with the actor as a young heartthrob until Romeo + Juliet. DiCaprio was 21 years old when he linked with Baz Luhrmann and Claire Danes on this reimagined Shakespeare story, and his acting in this modern adaptation doesn’t let up for a second.

Remember the scene where he looks at Juliet from the other side of the fish tank? Iconic. Plus, playing Romeo certainly helped him win the role in Titanic just one year later. I’ll never forget the interview DiCaprio did at the time when he said, “I want to get to a place where I’m just known as a really good actor who takes good choices.” If anything, the slip-up of takes/makes only proved just how young and earnest he really was.

Catch Me If You Can (2002)

There’s something perfect about DiCaprio’s rambunctiousness in Catch Me If You Can paired with the more traditional Hollywood sensibility of Tom Hanks trying to pin him down. It’s as if the plot of this inventive con man vs. the seasoned detective was actually about the previous generation of actors looking at this young kid who charms his way into winning any role—and still respecting the hell out of him for it.

When DiCaprio revealed in Esquire’s cover story that his own regret throughout his career so far is that he turned down Boogie Nights to work on Titanic, he didn’t mean that he wished he worked on Boogie Nights instead of Titanic—he meant that he wished he figured out how to do both. That’s how hungry and gifted DiCaprio already was at the turn of the century.

The Aviator (2004)

Of all the exceptional DiCaprio roles in the early 2000s that featured the actor spending the entire runtime of the film absolutely losing his mind—The Departed, Shutter Island, Revolutionary Road, and J. Edgar among them—The Aviator’s story of film producer and pilot Howard Hughes easily takes the cake. (As much as I love DiCaprio’s turn in The Departed, it’s more of an ensemble success).

DiCaprio would probably agree. According to the actor, he rewatches The Aviator more than any of his other movies. “It was such a special moment to me,” DiCaprio says in Esquire’s cover story. “I had worked with Marty [Scorsese] on Gangs of New York, and I’d been toting around a book on Howard Hughes for ten years… I was thirty. It was the first time as an actor I got to feel implicitly part of the production, rather than just an actor hired to play a role. I felt responsible in a whole new way. I’ve always felt proud and connected to that film as such a key part of my growing up in this industry and taking on a role of a real collaborator for the first time.”

The Wolf of Wall Street (2013)

DiCaprio may have won his first Academy Award for Best Actor for The Revenant, but it’s my opinion (and that of many others) that he should have won it for The Wolf of Wall Street two years earlier. Wall Street was his fifth film in collaboration with Martin Scorsese, and the two of them were displaying their full set of skills.

And no shade to Matthew McConaughey’s victory for Dallas Buyers Club, but DiCaprio is an absolute force in this full-throttle biopic of stock market fraudster Jordan Belfort. No one was more equipped to crawl to their car in a drugged-out panic than the guy who played countless deranged megalomaniacs in the aughts. Plus, in his characterization of a con man disguised as a master salesman, there’s a hint of Catch Me If You Can’s Frank Abagnale Jr., all grown up.

Once Upon a Time in Hollywood (2019)

It’s a shame that Killers of the Flower Moon (2023) ended up losing more money at the box office than it earned—that near four-hour runtime probably didn’t help—because it’s such an important film in this stage of DiCaprio’s career. Still, I’d argue that he transitioned into a Mount Rushmore figure (of the greatest living actors, of course) four years earlier in Quentin Tarantino’s Once Upon a Time in Hollywood.

The plot is just too perfect. DiCaprio plays a washed-up actor stuck filming movies overseas despite the fact that he’s one of the biggest actors on the planet in real life. After performing a little bit of revisionist history by fighting off Charlie Mansons’s followers and saving Sharon Tate from murder, he’s metaphorically “accepted” by Hollywood when she invites him in for a drink. It’s an insane ending, for sure, but it was proof that DiCaprio’s talents will go down in Hollywood’s history books.