If we are indeed at the tail end of the era of movie stars, it’s worth considering the career of one of the medium’s brightest lights. Leonardo DiCaprio is one of a few actors who can still open a movie at the box office simply by being its star, and one of a similar few actors who’s yet to be involved in a major franchise of any kind. Over the last quarter-century, he’s navigated the pitfalls of movie stardom at every turn. One of the most important transitions in DiCaprio’s career came 15 years ago, when he turned the corner into adulthood and starred as one of the famous men in American history in Martin Scorsese’s The Aviator.

Show Me All the Blueprints

By now, of course, DiCaprio working with Scorsese has become one of the most well-appreciated director/actor collaborations in decades. Since the start of the 21st century, DiCaprio has appeared in five of Scorsese’s films, including Gangs of New York and The Wolf of Wall Street. (Robert de Niro has, with The Irishman, now starred in nine Scorsese films.) Yet the star’s shift into the serious roles that now define him only fully came into being with his role as Howard Hughes in The Aviator.

Up to that point, DiCaprio had been both blessed and cursed with the kind of cherubic face that turned him into a teenage heartthrob for the back half of the 1990s. His roles in Titanic and The Man in the Iron Mask were well-liked (and Titanic was…y’know, Titanic), but also didn’t automatically hint at a more mature talent waiting to break out. Perhaps intentionally, it was around the time of those two films that DiCaprio became both impossible to avoid in the public eye and much more careful to choose his projects. (DiCaprio has, excluding documentaries and a short film, appeared in 28 films over three decades. 12 of those 28 films were released in the 1990s.)

The same year that DiCaprio co-starred in Gangs of New York, he played the lead in Steven Spielberg’s breezy period comedy Catch Me If You Can, as real-life con artist Frank Abagnale, Jr.. Frank was a young man who was able to use his boyish good looks to fool people into thinking he was both younger and older than he really was. In the film, we see Frank act like a substitute teacher, a commercial pilot, a lawyer, and a doctor, all while barely being old enough to drive. DiCaprio is quite charming in Catch Me If You Can, in what could almost read as a meta-commentary on the frustration of having to play older men while never looking like he could actually embody them from the inside out.

Hitting on All Six Cylinders

Though The Aviator wasn’t the first time DiCaprio and Scorsese collaborated, it was their most fruitful yet. (Gangs of New York is an often remarkable epic, but opposite Daniel Day-Lewis, DiCaprio comes up short in just about every scene.) As Howard Hughes, DiCaprio gets to showcase a range that hadn’t been evident in his past work. Part of the film documents how the tycoon hobnobbed in Hollywood, getting involved with actresses like Ava Gardner (Kate Beckinsale) and Katharine Hepburn (Cate Blanchett). So there, at least, we get to see DiCaprio at his most charming.

But Howard Hughes is as well-known for his intense obsessive-compulsive disorder as for any of his business accomplishments, and The Aviator doesn’t avoid that part of the man’s life. The first scene of the film, shrouded in darkness, depicts a young Howard being bathed by his mother as she teaches him how to spell the word “quarantine”, a sign of the trouble to come. Once we meet Howard as an adult, balancing his movie-studio aspirations with his desire to both fly and create some of the most powerful planes known to man, he’s gradually less and less able to cope with his OCD.

The way that Hughes devolves in the second half of the film, specifically when he holes himself up in a personal screening room, growing his hair and nails at an alarming rate without taking care of his body, is a truly stunning transformation. In a strange way, it’s almost purifying to watch DiCaprio expel the Teen Beat-style grace notes of his earlier work. At the start of the film, he’s still boyish. At the end, he’s been put through the ringer and come out a more adult, mature actor.

A Monumental Undertaking

When you glance at the titles in Leonardo DiCaprio’s filmography both before and after The Aviator, it’s fascinating to see the shift. His roles became more careful, if not always automatically successful. (There aren’t a lot of fierce defenders of either Blood Diamond or Body of Lies, which is appropriate because neither of them are very good films. But in both cases, DiCaprio was working with well-known filmmakers; it’s easy to see why he signed onto a Ridley Scott project, if only for the director’s reputation.) DiCaprio has managed to thread a needle that basically no other actor can do these days: he’s a choosy actor who works only with a select few filmmakers, on films that typically do very well at the box office and only add to the legacy he’s building.

That point about the box office is kind of remarkable to consider: in this decade, DiCaprio’s starred in just eight films, and only one of them grossed less than $100 million domestically. That would be the 2011 Clint Eastwood film J. Edgar, where DiCaprio attempted to play controversial FBI leader J. Edgar Hoover. (That, too, is a film with few defenders because that, too, is a bad film. It’s also a rare bad performance from DiCaprio.) The Aviator isn’t one of DiCaprio’s biggest hits but it also crossed the century mark at the box office with $102 million domestically. Though he’s not going to be seen in a Marvel Cinematic Universe title anytime soon, Leonardo DiCaprio is as close to a sure thing among his fellow actors at the box office.

The Aviator also served as the first time DiCaprio was nominated for Best Actor at the Oscars. It took him until 2015 to win that award for The Revenant, which frankly feels like the Academy awarding him simply because they forgot to do so with his past work. Where Gangs of New York was akin to watching a boy attempt to dress up in his father’s clothes, play-acting at being an adult, The Aviator marked the first time when DiCaprio’s ability to communicate experience and age shone through.

Reputation All Rolled Up

Since The Aviator, DiCaprio has continued to work with Scorsese on plenty more brilliant films. There’s The Departed, a film that finally netted Scorsese a Best Picture Oscar (another award seemingly intended to acknowledge the filmmaker’s other classics) and featured the movie star as a believably tortured and conflicted undercover cop. The Leonardo DiCaprio of 2002 couldn’t make that character believable, but just a few short years later, his intensity felt perfectly matched to the role of Billy Costigan.

Since then, DiCaprio’s worked on big-budget fare, such as The Great Gatsby (where he reunited with his Romeo + Juliet director Baz Luhrmann) and Christopher Nolan’s heady science-fiction film Inception. And this year, he reunited with Quentin Tarantino to play the neurotic has-been actor Rick Dalton in Once Upon a Time in Hollywood. Watching DiCaprio and Brad Pitt — who have both worked with Tarantino, but on separate projects — together is one of the film’s great delights. Yet we should also acknowledge that DiCaprio fully embodies the self-loathing and terrified nature of Rick Dalton in ways that both feel like meta-humor about the star as well as fully earned.

DiCaprio’s not the only movie star left in the world, to be clear. Pitt’s no slouch, as well as his Ocean’s Eleven co-stars Matt Damon and George Clooney. But Pitt, Damon, and Clooney have all struggled in ways at the box office — they’re still A-Listers, in that most everyone knows their names, but their presence in a film isn’t a guarantee of either box office success or critical and industry praise. DiCaprio, on the other hand, is a guarantor of both, in part because his absences never feel quite so long between projects (though it had been nearly four years between OUATIH and The Revenant) and in part because his taste is pretty damn impeccable.

The Way of the Future

And it all arguably started 15 years ago with the release of The Aviator, a film that could have easily been a victim of period-piece boredom or unintentional comedy. The ways in which Scorsese and DiCaprio depict the OCD plaguing Howard Hughes could have inspired derisive laughter, specifically the way that Hughes constantly repeats the same phrase or word when stuck in a verbal rut. But instead, it’s just as haunting in the closing scene when Hughes is trying to talk up the successful launch of the Spruce Goose (or, as he would rather call it, the H-4 Hercules) when he gets stuck on the phrase “the way of the future”.

Scorsese sharply cutting to black as Hughes keeps repeating that phrase, and not giving away anything else about Hughes’ life afterwards (there was a lot more of the “holing up in a screening room” and a lot less “hooking up with Hollywood starlets” in his future) is enough of a reminder that the eponymous Hughes of the title had a grim life ahead. There’s no photo of Hughes to show us who the real man was; there’s just DiCaprio. The actor embodies Hughes in these horrific moments as much as when he’s adopting the slick style of a movie magnate.

Leonardo DiCaprio is now widely accepted as one of the few remaining modern movie stars, a status that was far from certain 15 years ago. He’d stopped making quite as many movies, but a film like The Aviator could have sunk his prospects had it failed to coalesce. It’s not just that Martin Scorsese is a brilliant filmmaker capable of highlighting the inside-baseball elements of Old Hollywood. It’s that he saw something in Leonardo DiCaprio that hadn’t been made apparent yet in his work. He saw in DiCaprio a wealth of maturity waiting to get out, a force that’s been unleashed and unstoppable in the intervening 15 years.