With two confident, unsettling performances, the former boy wonder grows up (finally) and becomes the actor of his generation. 

He was already a successful, cheeky, sweet-faced TV actor when Leonardo DiCaprio saw the first two film performances that really turned his head. One was James Dean’s in East of Eden. The other, in Taxi Driver, was by Robert De Niro (whom the teenage DiCaprio had just been cast opposite in This Boy’s Life). “I never said, ‘This is what I’m going to aspire to be,'” he remembers, “because at that age, it’s something that’s so beyond anything that’s a possibility. But certainly it was something like, ‘Wow, I would love to give a performance even close to that someday.'”

Everyone significant involved with East of Eden was retired or gone, but he realized that the auteur behind Taxi Driver was very much around. From then on, the director he most wanted to work with was Martin Scorsese.

When he was about 18, DiCaprio even changed his representation primarily because he believed that his new agent could get him access to a Scorsese project, Gangs of New York. For a while, nothing happened, but not long afterward he met Scorsese in a New York bar after the screening of a De Niro movie: “I was blown away that he even knew who the hell I was. He started talking to me about Bob and how Bob told him about me…” It turned out that after This Boy’s Life, De Niro had advised Scorsese that this was a kid worth looking out for.

“I was dumbfounded that he’d seen anything I’d done.”

DiCaprio’s wish would eventually come true. And by the time Gangs of New York was finally made, years later, it was partly DiCaprio’s participation that allowed the film to go forward. (DiCaprio got the good news while eating pad thai in Thailand, where he was filming The Beach. But even then it was delayed, and DiCaprio was ready too soon: “I started working out and bulking up to be this Irish gangster, and the movie kept getting postponed, so it was like a year and three months of having to work out, having to eat.”)

Two more Scorsese-DiCaprio films have followed: the Howard Hughes tale The Aviator, which DiCaprio calls “the most memorable and rewarding filmmaking experience I can recall,” and the recent, electric tale of multiple deceit in Boston cops-and-Mob-land, The Departed. “The guy’s a mentor to me, that’s what it is,” says DiCaprio, “and I’m blessed, honestly, to be in his presence when making these movies, because you cannot stop learning… It’s incredible. I couldn’t have hoped for anything more.”

In The Departed, DiCaprio may not have the flashiest role but he has a quiet assurance that allows him to channel the darker currents at the film’s turbulent center. No contemporary Scorsese interview is complete without some kind of testimony to DiCaprio and their bond: “His face is a battlefield of moral conflicts.” “There’s an inner story going on with DiCaprio that somehow I was able to tap into, which is similar to what I feel.”

DiCaprio says he believes Scorsese still refers to him as “the kid,” though not to his face.

“Thankfully,” says DiCaprio, “he sees something in me that makes him want to work with me.”

*****

We talk on the patio of a suite at the Hotel Bel-Air in Los Angeles, where DiCaprio explains that he is jet-lagged from a brief trip to Europe to meet with a director he won’t identify about a project he won’t discuss.

There’s a supposedly scientific study reported in the Los Angeles Times today proving that famous people are more narcissistic than others.

“I’m sure. Isn’t that the very nature…? It wasn’t mind-blowing evidence, right? I thought you were going to tell me the news about Pluto not being a planet.”

No, but I’m not happy about that.
“Me neither. I’m a Scorpio—I’m supposed to be ruled by Pluto.”

So you’re f**ed.
“I know. I’m no longer part of the Zodiac.”

What does it mean you’re supposed to be like?
“Scorpios? Passionate [snorts derisively]…driven…secretive…highly sexual…and something else. I forget. And I know what your next question’s going to be. ‘And how accurate do you think that is, according to who you are, sir?'”

So does that seem like a vaguely reasonable summary?
“Very vague, yeah. Very vaguely.”

*****

For his latest movie, Blood Diamond, Leonardo DiCaprio becomes a Zimbabwean gem smuggler hemmed in by some of life’s usual hazards—greed, lust, danger, conscience—while he hunts down the one huge diamond he imagines will solve all his problems. Though it is far more than a film made simply to express a political point, Blood Diamond does attack the diamond industry in two ways. One of these ways—the diamond industry’s sometime indifference to the source and human costs of the diamonds it sells (particularly those from Sierra Leone)—is presented as a matter of recent history. But the other—the suggestion that the diamond industry is a global scam based on artificially restricting supply to maintain the high prices of gems with little intrinsic value—seems more timeless, and hence more of a challenge.

DiCaprio says that he has bought diamonds—”girlfriends, my mom”—but not recently. When I suggest that the movie portrays diamond consumers as people buying into some kind of marketing myth, he responds, “What isn’t a marketing myth, at the end of the day? To me, the point is to say we’re all consumers.” And so, he suggests, we should all be careful and responsible about everything that we buy.

I guess there is another weird kind of resonance in Blood Diamond in that this is the second movie you’ve made about searching for a big diamond.
[puzzled] “What’s the other one?”

That famous one with the boat.
“Oh. Right.”

*****

Crudely speaking, so far there have been four ages of Leonardo DiCaprio, the actor. First, there are his years as a teenage TV pinup, which began when he was cast on the one-season sitcom Parenthood and peaked when he joined the cast of Growing Pains.

Second, there is a remarkable, precocious, teenage and slightly post-teenage work in movies like This Boy’s Life, Romeo & Juliet, The Basketball Diaries, and What’s Eating Gilbert Grape (for which he got his first Oscar nomination).

Fourth, there is his impressive and self-assured recent climb into manhood: the Scorsese movies and also his deft Steven Spielberg romp Catch Me If You Can.

And between these – the third age of DiCaprio – comes the once-in-a-lifetime disorienting meteor strike of the most successful film of all time, Titanic.

“I know, it’s certainly the biggest thing I’ll ever do. You know, not a bad movie at all.”

In one of the interviews you did before you made Titanic, you said, “I just don’t want to be big box office yet. The more you stay low-key at a young age, the more you have room for that stuff in the future…..”
“Right. It was weird, because my initial reaction was to not do it because of those reasons. And then it became something that I just wanted to try. On a whim! [laughs] I wanted to try it on a whim, to see what it was like to make that type of film. And this seemed like – and it was – a film that wasn’t just about the action, it was about the love story, and I’d never really done anything like that. Something that had a budget like that, that had effects that were out of this world and insanely complicated, that had a climactic, action-orientated ending. But what I wanted to do was to try something completely different than what I’d been doing. Nobody could have foreseen the impact. It’s mind-boggling.”

You’ve always been careful to not seem ungracious about Titanic.
“I’m not ungracious about it, because it absolutely gave me the opportunity in every possible way as an actor to steer the course of my own professional career, which is what almost every actor dreams of.”

Leonardo DiCaprio first saw Titanic at a test screening in the Los Angeles valley; he remembers the audience’s excitement. Nevertheless…
“I had no idea. Even while it was happening. This time after – if you want to talk about the effects of what it was like to be in that sort of bubble – that was insane. It was a weird time, man. It felt like I was on the run. [laughs] Like I was on the lam or something. Like I was The Fugitive.”

*****

“Fortunately, I grew up close to Hollywood. And I certainly would not have been an actor or entered the acting industry if it hadn’t been convenient like that. I probably would be doing local theater or something, but I don’t know if I would have had the courage to have come out to Los Angeles, set up shop independently, and pursue the career with such vigor and passion.”

So you don’t feel like “If I’d grown up in Des Moines, there was so much of this acting stuff inside me that I would have had to burst out of town and find its home”?
“No.

Strange to think that geography plays such a big part in destiny.
“Oh, absolutely. But the basic fact that my stepbrother had done commercial and television spots, and he was 8 years old and had an agent – the mere concept would never have occurred to me. I would have just stayed in school and stayed in drama class and have that to be my outlet and, on career day, figured out how to be a biologist or a travel agent. But I was not successful at getting an agent when I was 9 or 10 – I was a break-dancer, and my hair was in some sort of weird shaved Mohawk or whatever, and that wasn’t conducive to Cheerios commercials.”

I presume you don’t have many days now when you suddenly start dreaming about the travel-agent life you could have had?
“No. The reason I wanted to become a travel agent was to be able to get free trips. But I remember being really disillusioned on career day, because I knew I had absolutely no idea what I could seriously take on as a profession. I tried again to get an agent, and I succeeded, but there was a period of a year where I almost quit, because I went on a hundred auditions and I didn’t get one job. Finally you get to the point where you’re so disillusioned by the process that you kind of say ‘I’m not going to care so much about what these people think of me.’ And that’s when I got my first television show.”

Thanks to the indiscriminate and lazy wonders of YouTube, random snatches of DiCaprio the teen star live on. In one of his first interviews, filmed on the set of Parenthood and taken from a program called 50 Cutest Child Stars, he explains his motivation as an actor, oozing a bratty, grinning, cat-got-the-cream geekiness: “I like to act. I like… I think it’s going to get me ahead in life. I must admit I like the attention.”

“It’s hard for me to draw upon what was exactly going through my head there, but I can definitely say that was a direct result of finally having others kids in my school acknowledge my existence. Finally getting a little attention at school. Because I was an entirely unpopular student, so to have someone say, ‘Hey! I saw you on The New Lassie, dude! Awesome!’ would have me leave school gleaming.”

Why do you think you were so unpopular?
“Why? Because I was.”

When I ask him what it was like acting opposite Jack Nicholson, he refers me to the documentary Stanley Kubrick’s daughter made about the making of The Shining and in particular to the remarkable footage in which Nicholson, in preparation for a scene, starts jumping and jabbering and contorting himself in a terrifying and seemingly insane manner. “It’s him amping himself up,” says DiCaprio. “It’s almost like a coach pep-talking himself.”

And he was doing that while you were acting next to him?
“Sure. It’s a part of his… What was fantastic was finally sitting there as an actor doing a scene with him, being able to sit at a table with him and not being able to predict anything he’s going to do.”

Before one scene, the prop guy tipped off DiCaprio that Nicholson had somewhere near him, a gun, a fire extinguisher, matches and a bottle of whiskey.

“You have to expect the unexpected,” says DiCaprio. “You have to walk on the set knowing that you don’t know what’s going to happen.”

*****

Tobey Maguire first met Leonardo DiCaprio at the audition of Parenthood. “I would see the same circle of kids getting close,” Maguire remembers, “and Leo was kind of new to me, and I actually just kind of wrote him off. I was sizing up my competition, I guess, looking around. He was so relaxed he seemed unfocused. But in fact, he was just really relaxed and prepared.”

In his first real movie (no one sane remembers much about Critters 3, including DiCaprio), This Boy’s Life, DiCaprio played the young (Tobias) Wolff. Robert de Niro was already cast as Wolff’s stepfather, and the final eight or nine young actors in contention auditioned opposite him. Maguire, who was also auditioning, says that he had just started reading books about acting history and techniques, and about the kind of preparation actors like De Niro would do, and that may be why he froze: “I just was so freaked out by his presence… I don’t think Leo was as aware at the time. There wasn’t that extra weight for him to go and meet De Niro.”

DiCaprio says he did realize that this wasn’t an audition he could just float through. “I knew I had to do something to stand out.” In the scene, when De Niro presented him with a virtually empty mustard jar and asked him whether it was empty, instead of merely saying that it was, he yelped the answer with a kind of wild, unexpected, unintimidated defiance, and it worked. “There was a whole generation of actors there, and I happened to get lucky that day, and I guess I made a decision that sort of altered the course of my life.”

He still had a lot to learn. “It was all mind-boggling stuff to me,” he recalls. I’d just never seen people take it that, sort of, seriously, for lack of a better term.” He credits the director, Michael Caton-Jones, for showing him how such a thing could and should be done. Suddenly, he wasn’t another teen TV star; he was an actor. “He knew that if I was awful, his film wouldn’t have worked. So he took me very seriously, which is what I needed… I have the most unbelievably fond memories of that movie. Whenever it comes on cable or anything, it gives me that little bump in the throat. I get a little bit emotional when I see it, because I was so excited and happy to be there. Just being there as a kid, working with Robert de Niro and being the star of a film, it was like winning the lottery.”

I was reading an old interview with Michael Caton-Jones, and he said about you, quite clearly affectionately, “He was a smart-mouthed little f**,” and even provided the example. Ellen Barkin apparently lectured you about clowning around on-set with her and Robert De Niro and said that you should behave more like the two of them. And you’re supposed to have retorted, “Like the two of you? Let’s see, on one hand he did Raging Bull. On the other hand you did Switch. And you’re the one who’s telling me what to do?”
[laughs, wincing slightly] “Oh boy. Yeah. I was a little brick back then. Wow.”

Do you remember saying that?
“I don’t remember saying that exact quote, but I wouldn’t doubt it. I’m sure I did say something to that effect. But that was part of the reason, I believe, why he cast me. That was my life – I was always the smaller kid during junior high and high school, where I hadn’t had my big growth spurt, so I would defend myself with my mouth. We’d have these things in school called bagging contests, where you basically sit and berate and insult each other for an hour, and I had to learn to hold my own, because I couldn’t do it physically. Live or die by those in school – it’s of the utmost importance.”

*****

When Leonardo DiCaprio first saw This Boy’s Life, he had no idea whether he had done anything good, but there was one part of the experience in which he could take an uncomplicated pleasure: “The greatest moment was watching the pride that my grandfather had. That’s the image that I remember the most. Because he’s a coal miner from Germany who worked in the coal mines for thirty years, went through World War II with his family, moved to the Bronx, had one of the most hard-core lives you could ever imagine, worked his entire life. And to see him proud of his grandson…

“My grandfather came from an era where they would work fifteen hours, six to seven days a week, and still not have enough food to feed the family. The stories that my mother tells me of what it was like in war-torn Germany for a peasant family, basically. Pretty amazing stories.”

Did he have to fight in the war?
“Yeah.”

On the German side, I guess.
“Yeah. Well, listening to my grandparents tell their stories of the propaganda that was going on then, for people that weren’t necessarily educated and didn’t keep up with politics, they really genuinely didn’t understand what was going on. Really didn’t.”

In what ways are you most German?
“I can be very blunt, to particular people in my life. Straight-forward. I don’t sugarcoat things. But that isn’t to everyone; that’s only to people I care about. And work ethic – they have a tremendous work ethic in Germany. My mother and my grandmother both came from war-torn Germany, and they have much more nuts-and-bolts attitude toward life. A lot of things are black-and-white. I do have that in me, and I’ve gotten that from them. When you’re dealing with the artistic world, you can’t always look at things as black-and-white, but it helps on the business side.”

And how are you most like your father?
“He’s taught me patience more than anyone else – tolerance with people – and [he’s] someone who’s always pushed me to see the other side of a viewpoint. He’s opened my mind to a lot of things.”

And you knew Timothy Leary?
“Of course Timothy Leary. Yes!”

Had you known him throughout your childhood?
“Yeah. We’d been to his house many times. He was really into what the future would bring and felt intrinsically a part of the future, even in his later days, when he knew he was passing. He looked at death like he was passing in a different dimension, not that he was dying. It was pretty fascinating to see a man in his last days like that.”

*****

DiCaprio followed This Boy’s Life with an even better role, in What’s Eating Gilbert Grape. This marked the first time Dicaprio did any research for a role. He spent a week or two hanging out with mentally disabled children in a Texas home, compiled a checklist of around a hundred mannerisms, and then showed them to the film’s director, Lasse Hallström, one by one, to find out which he liked: “The way he uses his fingers and does this, the hand movement, the way I would walk, the kind of pitch of voice, the way he would read, the language he would use…” The character that resulted was far more than a compilation of tics; he was remarkable, extreme and believable.

This was a first in a series of bold and compelling pre-Titanic roles.

Even back then, DiCaprio would politely choose to share next to nothing about his romantic life, such it was (“I would love her as a person”, he told me of an unnamed girlfriend, “but I don’t know what’s it like to fall in love.”), and he has since stuck to that without fail.

Perhaps he might say a little more if asked a little less.

What do you understand about love now that you didn’t understand when you were 18?
“Boy, you got some heavy questions, huh? What I understand now? That it’s a huge commitment. To embrace it properly. And that at 18 years old, you have almost no chance of having a love that will survive for the rest of your life, but you don’t know that at 18.”

That’s one of the great but slightly sad things about being 18.
“Yeah. But it is kind of sad, because you kind of do know that the next some-odd years of your life, there’s no chance of anything surviving at all. Without repeated heartbreak and the reconciliation – that’s the only way.”

Do you think you understand more or less about women as you get older?
“More. Through trials and tribulations.”

Do you get happier as you get older?
“Yes. Definitely. Don’t you agree? I think teenage life is filled with narcissism and giant mood swings that are unnecessary and constantly inflating problems to phenomenally unrealistic proportions.”

Leonardo DiCaprio has been getting older. But very, very slowly.  “It’s a fact”, he concedes with an edge of patient amusement. “I have looked young for many years.”

Sensibly, he chooses to see this as a positive thing for an actor, one that has allowed the cloaks of younger men to rest easily on his shoulders, rather than be frustrated that biology and physiognomy may have short-changed him of a gravitas he has otherwise deserved. Anyway, it seems as though his life clock may have been ticking slowly on the inside as well as on the outside, and has a theory why this may be so.

How old do you feel now?
Not my age. [He is 32.] Younger. Midtwenties. Because if you accumulate all the time that I’ve had on-set where I wasn’t actually living life, you could probably substract years and years. That’s not like lifetime.”

So if you filmed twelve months a year—
“I’d never age. Physically, emotionally, or mentally.”

*****

When we meet for the final time, at the Peninsula hotel in New York, Leonardo DiCaprio leads me up some stairs to a table in a restaurant-bar.

As we sit and talk, he notices something happening through the second-floor window behind me. By chance, this hotel bar faces the Manhattan showroom of the world’s largest diamond company, De Beers (one that no one, surely, would ever confuse with the fictitious market-molding multinational jewel sellers Van De Kaap in Blood Diamond). And tonight they’re having a party. “A giant De Beers party, swinging and rocking”, DiCaprio says. It seems fitting.

Since we last met, he has been dashing across the world promoting his two movies, and he says that he needs it to stop.  “For example, I’d like to absorb sunlight. I haven’t seen the sun for almost two weeks now.”

Shall I write, “As he speaks, he looks sadly out of the window toward the waning sunset, knowing that another day has passed him by”?
“Boo-f**ing-hoo, right?”