The Moment Leonardo DiCaprio Became a Man

by Tom Junod for Esquire | Photographs by Max Vadukul | May 2013

“Most recently, the last few years, I feel way more comfortable than I’ve ever felt. You always talk about that, and then one day you’re like: If they don’t like this, well, f* ’em. What can you do? It’s a resignation to life and who you are. Hey look, I’m pretty well-formed as an adult now. I don’t have to impress anybody. You ask yourself these different questions: What do I want to do? Interesting question: What do I want to do? What makes me really happy? I’ve learned all these things that I’m supposed to do. I know I’m supposed to be in that place and do that thing . . . but to really, deeply ask yourself that question—What do I want to do?”

Guy’s sitting in a chair, in the big empty conference room of a big expensive hotel. Leonardo DiCaprio’s been sitting in the chair a couple hours. He’s been all twisty, one leg slung over the other. He’s one of those guys who has to invest a lot of energy into staying put, and so as he makes his speech, he’s also untangling himself, putting his hands on his knees and his feet on the floor.

Guy walks into venerable Hollywood establishment Dan Tana’s. Different guy—not Leonardo DiCaprio. But this guy, Rick Yorn, has something very valuable in a place like Dan Tan’s back in 1999—he has Leonardo DiCaprio, whom he has represented as a client since DiCaprio was a kid. When the kid was just a teenager, he made two movies that announced his talent to a new generation of moviegoers. And then he made Romeo + Juliet and Titanic, which made him, as a very young man, the biggest movie star in the world. So when Yorn goes to Dan Tana’s to meet some friends, he gets summoned to the table of a tanned old man in big black eyeglasses, Lew Wasserman.

Wasserman is the wise old owl of Hollywood. He’s a combination rabbi and mobster, part Caesar—he invented the industry he lords over. And now he wants to speak to Yorn about his client.

“Lew was old and near the end by this time,” Yorn says. “He died a year or two later. But he knew I was Leo’s manager, and he wanted to give me some advice.

“He said, ‘Only let them see him in a dark room.’ It took me a minute to figure it out. But what he meant was only let people see him in the movie theater. That’s the dark room.”

It’s harder now, Yorn says. It’s harder to live out of the public eye than it was in Wasserman’s day. The kid lives in a celebrity surveillance state. Still, he’s done a pretty good job of “maintaining his mystique,” Yorn says—of making his living in the dark. And besides, he’s not a kid anymore.

A few years ago, he was on a plane. He was flying to Russia. He was going to meet with Vladimir Putin at a conference Putin organized to help save the Siberian tiger. He’s taken the tiger as his cause. He was on a Delta flight to Moscow. He often flies commercial according to friends who say that, after all, he’s just a regular guy. The flight was already out over the ocean. He was looking out the window when he saw one of the engines explode.

He was, like, the first to see the engine explode, so he didn’t know if the engine had really exploded. He’s learned how to sleep on planes, so he thought maybe he was dreaming. He thought to himself, Holy sh*! but he didn’t want to come right out and say that. Then some guy in the first-class cabin said “Holy sh*!” really loud, in a heavy Russian accent. Then the lights went out. Then the other engine, the second engine, went out. He’s on this plane out over the ocean, the lights are out, and the silence is, like, consummate. Sure, there are people screaming and shrieking and crying and praying, but the silence is what undergirds everything, the silence is what’s inspiring people to make all that noise. The plane’s gliding, dude. The pilots had to shut down the working engine to make sure that the engine he saw explode wasn’t on fire.

He had been in a similar situation once before, when he was tandem skydiving and the chute didn’t open. He was just falling, falling, falling, in that eerie encompassing silence of unbroken descent . . . while his instructor worked to cut the line and deploy what turned out to be a second tangled chute. So he recognizes this feeling. He’s felt it before. He says to himself, This is not good, whereupon he hears the Russian guy echoing him in that heavy Russian accent, This is not good. . . .

Then the second engine restarts, and they go up . . . but now they have to fly around for an hour, dumping fuel into the ocean, because otherwise they’d be too heavy even for the emergency landing, the descent into the swirling red lights assembled on the tarmac. He can see them, too, through the window in the distance, the consoling fire instead of the annihilating one, getting closer and closer—and then they land, and he signs autographs for the crew.

And then he has to figure out what to do next. He has to decide whether to get in the air again. It’s not like he wants to, because when you fall like that, you realize something about the air—it’s air. It’s not solid, and it can drown you. But he has—and this is what people don’t realize—responsibilities. So he finds a private plane willing to go right to St. Petersburg. By now, though, there’s weather over the Atlantic, and the private jet takes such a beating that it can’t reach Russia on the allotted fuel. There’s an unscheduled landing in Helsinki. Still, he makes it to St. Petersburg, makes Putin’s conference, and he writes a check for the tigers—$1 million of his own money. When Putin addresses the conference, he asks Leonardo DiCaprio to stand up. He recounts the whole story. And then at last, speaking in Russian, he pronounces DiCaprio a “nastoyashi muzhik”;

A real man.

He does not yet look like a real man. Not with that face. It’s a famous face—famous for looking young. He’s thirty-eight years old, but he doesn’t look substantially different than he did sixteen years ago, when he went from promising film star to international pop star, and his fame jumped the boundaries of Lew Wasserman’s dark room. 

“The Leo I know now is a man. The Leo I knew at nineteen was a boy,” says Baz Luhrmann. In a way, Luhrmann was the last to see DiCaprio before he became, in Luhrmann’s words, “as big as the Beatles.”

Now, twenty years later, he’s directed DiCaprio in this summer’s Great Gatsby. And he speaks of DiCaprio’s maturity with a reverence born of surprise and relief. “I tell people that they have to understand that Leonardo’s only ever been on a movie set. There’s absolutely no question that he’s grown and matured, but he’s grown and matured in a way unique to Leonardo. Nobody knows the kind of fame that Leonardo knows, and it’s far more common for people to become deranged by it. It’s generally quite toxic. But somehow it hasn’t been toxic for Leonardo. He’s been very good at making choices for his self-preservation.”

Leo was maybe twelve. He was on his way home from school with his mom. He saw a kid making an episode of a TV show on a street in L. A. He recognized Tobey Maguire from auditions. So DiCaprio told his mother to stop the car, like, now. “I literally jumped out of the car,” he says. “I was like, ‘Tobey! Tobey! Hey! Hey!’ And he was like, ‘Oh, yeah—I know you. You’re . . . that guy.’ But I just made him my pal. When I want someone to be my friend, I just make them my friend.”

It worked as well as it could. Twenty years ago, when Baz Luhrmann invited him to Australia to start working on Romeo + Juliet, DiCaprio traded in his business-class ticket for five tickets in coach and brought his friends with him.

“I thought, He realizes he’s never going home,” Luhrmann says. “So he brought his home with him.” Luhrmann was right, on both counts. The level of fame that DiCaprio achieved when most of his friends were still struggling to get parts was both liberating and obliterating. On the one hand, he could do anything—have any woman, make any movie. On the other . . . well, “I was like, Oh, my. I really didn’t understand what fame was and I didn’t understand what being in a giant hit was and I didn’t understand what a giant hit Titanic was compared with other giant hits. There was no rule book. There was nobody to navigate me through the experience of being watched all the time and nobody to tell me how to be normal when everybody is acting and looking at me differently.”

All the guy did was make movies. There were women, of course, some of them famous beauties, but, as he says, “six months of being on location or being off in Morocco or someplace like that is not the best thing for a relationship.” He got a dog but had to give it to his mom to take care of because “if I had to feed it, it would starve and die.” Over the last two years, he made three movies, Gatsby, Django Unchained, and The Wolf of Wall Street, and when he finally came home, his friends were like, “Dude, you don’t even live here anymore.”

No, he can’t have a normal life. But his friends can. Connolly lives in the same neighborhood as DiCaprio—“ten houses away,” he says. So does Maguire. And so they go back and forth. They play basketball on Saturdays, they watch sports on TV, they talk about the work they want to have done on their houses or about nothing at all.

And DiCaprio? He’s Uncle Leo when he’s in the neighborhood—it’s what he fights for, because it means freedom.

But what is his life like? Nobody knows, and when you tell him that nobody knows, he says, “Really? Huh—I thought it was the exact opposite.” He has done his best to let us see him only in the dark. It is harder to see what his friends have the opportunity to see. They see a loyal and generous friend—a member of their weddings, a guy who served as a pallbearer at the funeral of Kevin Connolly’s mother and who gave Kate Winslet away when she was recently married. Asked if Leo has ever been heartbroken, Connolly says, “Absolutely—big time. He has been 100 percent heartbroken by a girl.” But they also see, by consensus, a guy “fiercely protective of his privacy,” whose privacy they are obliged to protect. They are not only protective of their friend Leo; they would not be in his life if they were not.

“His friends are supposed to be the measure of his normalcy,” says a Hollywood producer who has worked closely with him. “But how normal is it for anyone to have the same friends he had when he was thirteen years old? Ask yourself—how many of your friends from that time do you still hang around with? Things change. But for Leo, nothing ever really changes.”

A little while ago, he had to make a decision. It was a big one. He had to decide whether he wanted to star in Baz Luhrmann’s Great Gatsby as Gatsby. Luhrmann had asked if he wanted to do it. It was a big, iconic role but that’s not why DiCaprio had to think it over. Originally, the project belonged to Sony and DiCaprio has his deal with Warner Brothers, but that wasn’t the reason, either. Luhrmann had been on the phone with DiCaprio, and he knew that DiCaprio was cautious about playing Gatsby for a very specific reason:

Gatsby is very good-looking.

Luhrmann had been through this before with DiCaprio. He had been through it when he asked DiCaprio to play Romeo opposite Claire Danes’s Juliet. DiCaprio had made his name playing what were essentially character roles, and he understood that the glamour of Luhrmann’s conception of Romeo would change his life. He’d been right. Now with Gatsby, he was looking at the same kind of decision. He had spent the decade and a half since making Titanic on the run from his beautiful face, from his compulsive movie-star charm, and from movies that required him to be attractive in order to work. He’d worked with Steven Spielberg, Ridley Scott, Christopher Nolan, Clint Eastwood, and five times with Martin Scorsese. He takes very seriously his responsibilities as a leading man. “There’s so much more responsibility in being a lead,” he says. “There’s the arc of that character and how each of your decisions affects the story line. When I was in Gilbert Grape, I could spit spaghetti out and climb trees and make any noise I wanted, because Johnny had to move the story along, for the story to make sense.” And now he was hesitant to be in another movie that to some degree was about his looks. . . .

“Getting Leonardo to make the decision to play Romeo when he was nineteen was high drama,” Luhrmann says. “He said, ‘I won’t do that again’ with Gatsby, and he did it again. It was the exact same thing.”

What turned DiCaprio was the book. Luhrmann gave him a first edition, and DiCaprio says that he wound up reading it at least twenty times. He discovered a character who is “this peasant who is unaccepted by the American aristocracy,” DiCaprio says. “He will never be them and he will never truly belong.” He was not only attractive—Gatsby had to be attractive in order to manipulate people, and he had to manipulate people to achieve what Luhrmann calls a “noble cause—the love of a single woman.” And once DiCaprio saw that attractiveness was fundamental to any true characterization of Gatsby, he decided to take it on. He wound up giving a performance in which “he’s not hiding from the fact that he can be attractive onscreen,”

Luhrmann says. “Leonardo took the immense leap of not fearing the natural charismatic ability that Gatsby requires and that in many of his movies Leonardo has been shy of.”

“You have to understand—in this industry there are a lot of other people who are passionate about becoming actors. You wonder who you are going to become. You’re not even a formed man, and you try to decide what’s going to become of you for the next eight or nine years. And I always thought of myself as the underdog because I didn’t have nice enough clothes or maybe my hair didn’t look good. And so you have to understand—getting your foot in the door is like winning the lottery. It’s literally like winning the lottery if you get to have a career. And I’ve always felt Okay, now I’ve gotten this shot, and I’m lucky to have gotten this shot, and if I don’t do this to the best of my ability—if I don’t work my ass off and make a life of it—I’ve squandered this incredibly golden opportunity. And that’s always been what has propelled me.”

Ask Clint Eastwood why Leonardo DiCaprio is a fine actor and he answers in three words: “He enjoys it.”

And ask Leo himself how he answers his own question—What makes me really happy?—and he responds as though the answer has been self-evident all along: “I think I’m doing it!”

One day, in 2010, Leo DiCaprio had to decide what species to save. He called Carter Roberts, the president of the World Wildlife Fund, and asked him to come to L. A. Roberts went. They met at a restaurant in Hollywood, and “we have this long lunch talking about the magic of having a champion for the cause of every animal.” DiCaprio wanted to champion the tiger. He used to go down to the La Brea tar pits to look at saber-toothed tigers drowned and preserved in tar and wonder how such creatures had disappeared from the earth; he used to go to the Natural History Museum and try to think of something else he wanted to do besides become a famous actor. And now that he is a famous actor, he doesn’t just like tigers; he thinks a world without them—or a world in which they only live in zoos—would be a “f**ing nightmare.” What’s at stake is not simply the fate of the tiger—but of wildness itself. “World leaders,” says Carter Roberts, “like Vladimir Putin, like the king of Bhutan, and like Leo, see a little of themselves in tigers. They’re at the top of the food chain, they’re killers, and they’re incredibly good-looking. What’s not to like?”

Guy goes to Leo’s house to make him a coffee. The guy’s name is Todd Carmichael. He’s an adventurer who develops coffee farms in very remote and impoverished parts of the world. He spawns little economies by buying the coffee, roasting and selling it. He also believes that “every man should have his animal.” Carmichael’s animal is the Indonesian orangutan. When he heard that one of Leonardo DiCaprio’s animals is the Sumatran tiger, he gave him a call. “I thought that the conversation would last two minutes. But it kept going and going, and by the end we had a product. I said, ‘I’m going to make you a coffee.’”

He meant that he was going to create a coffee for Leonardo DiCaprio. DiCaprio would put his name on it, and Carmichael would sell it under his brand name, LaColombe, with all profits going to the Leonardo DiCaprio Foundation. The coffee would be called Lyon. But first DiCaprio had to approve it. So Carmichael went out to L. A. to have lunch with Leonardo DiCaprio and create a Leonardo DiCaprio “taste profile.”

The lunch took place at DiCaprio’s house. The food was brought in. Carmichael offered different kinds of foods to DiCaprio and noted whether or not he liked them. “I’d give him some frisée, and he’d shake his head. And I’d say, ‘So no bitters?’ ‘No, no bitters. No way, frisée!’”

In many ways, it was the quintessential Leonardo DiCaprio experience. It occurred in the house where he feels comfortable. It was for a cause, but it allowed him to exert control. Lyon coffee would exist as an expression of both his generosity and his ongoing efforts of discrimination.

And so Carmichael bought the coffee and roasted the beans, and when DiCaprio tasted it, he was amazed at how perfectly it captured him.

“I felt like a genius,” Carmichael says.

He acts in his chair in the hotel conference room. He performs. He can’t stop himself any more than he can stop himself from being what Baz Luhrmann calls “attractive.” He says that, for him, the ultimate unfiltered world is the ruin of Pompeii. You have to go, dude. You have to wake up and go early in the morning, when nobody is there, when there are no tourists around, and see the molds these people made in the ash at the moment they died, two thousand years ago. They’re captured for all time in all these campy Nosferatu poses of death . . . and now Leonardo DiCaprio, in his chair, begins performing, begins assuming these poses, curling up on himself, bringing his hands to his face, enfolding his cheeks with his long fingers.

He never really stops performing after that. He’s excited; he’s an enthusiast; he likes to tell you where to go and what things to see. He’s returned to L.A. after two years of making movies, and though he feels more comfortable with himself than ever before, he’s also trying to decide whether or not to take a vacation. He’s just talked about asking himself what it takes for him to be happy. “I’m talking about in any situation in life. In anything that might come up. I have a production company, I have a foundation, I have a lot of responsibilities. Not family—just a lot of responsibilities. But things take care of themselves when you’re gone. Then you come back, and it’s like, You gotta be here, you gotta be there, you gotta do this, you gotta sign that, you gotta read scripts, you gotta go to the photo shoot, you gotta do the interview, you have meetings, this person needs you, that person wants you, and it’s like, “Wait a second, can I just please . . . take a breath?’” And he keeps going like this, keeps talking faster and faster until he’s a little out of breath, theatrically out of breath, and then he raises his hands again to his face acting out the agonized ending of the long-dead inhabitants of an ancient Roman city.

This article has been edited for girlsspeakgeek.com. The complete story appeared in Esquire, May.2013.

May 1, 2013 | draft | this post contains affiliate links