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Sometimes even the King of the World can't catch a break. Leonardo DiCaprio, famous since childhood, superstar since adolescence, and arguably the most successful actor of his generation, still struggles to be taken seriously. This despite the fact that he has now made five movies with the most respected director of his generation, Martin Scorsese.

But maybe that's the problem. Both artists are trying to jump the long reach of their own shadows. DiCaprio has been too famous and too pretty to deserve credibility. And Scorsese's work with DiCaprio – Gangs of New York, The Aviator, The Departed, Shutter Island – has been rather hopelessly measured against the director's formidable, era-defining eight-movie run with Robert De Niro, and the common consensus has been that Leo is no Bob. Because the De Niro/Scorsese team-up produced some of the most enduringly memorable and influential movies of their era – Mean Streets, Taxi Driver, Raging Bull, Goodfellas – they are held over the director's work with DiCaprio like a grand piano suspended by thin wires. Here's a typical comment, posted online around the opening of Shutter Island, Marty and Leo's fourth duet. As the writer freely admits, he hadn't even seen the movie yet, but he just knew it probably sucked because DiCaprio was in it: "I just watched the trailer for Martin Scorsese's upcoming thriller/horror/suspense/police/star-vehicle Shutter Island and all I can think of, once again, is just what the heck Scorsese sees in Leonardo DiCaprio?"

Well, look at him in The Wolf of Wall Street (opening Christmas Day), the 39-year-old actor's most recent and fearlessly articulated turn for Scorsese, and you can see exactly what the moviemaker has seen in the movie star all along: an all-American pretty boy with the heart of a viper, an incorrigibly egotistical striver with sociopathic tendencies, and a man for whom enough is never, ever enough.

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This is the DiCaprio persona Scorsese taps into in his epically acerbic, Billy Wilderish boardroom satire inspired by the utterly amoral gimme-binge of a life lived by the Wall Street chop-shop brokerage executive Jordan Belfort, and the reason it works so well – which is to say it's possible to be mesmerized and revolted by it in equal measure – is precisely because Jordan Belfort is being played by DiCaprio.

If it was De Niro, even the younger De Niro, this vain, soulless viper's endless spree of deregulated acquisition would be the stuff of clammy, unnerving white-collar evil. But played by DiCaprio, who brings to Belfort's incalculably destructive antics the sheer, frat-boy delight of being young, rich, famous and immune to the mortal rules of decency, the guy's like a just-out-of-high-school movie star who's been handed the world on the end of a coke spoon. Or, and I think this is it, maybe just starred in the biggest movie of all time.

I'm guessing Wolf 's Jordan Belfort is a version of what Leo must have been like when Leo surfaced – a notorious non-stop, globetrotting party animal – after Titanic, and I'm further guessing that's exactly what Martin Scorsese had in mind.

It's no mystery why filmmakers have gone to the same performers once they've landed a good one. Tim Burton and Johnny Depp come to mind, as do David Cronenberg and Viggo Mortensen. If the experience has been positive, if the filmmaker feels the actor understands him or her intuitively or vice versa, the economy of collaboration can't be underestimated. Making movies is a massively complex, expensive, labour-intensive and time-consuming process, so anybody who knows what you want without being told is a good person to have around. This is why filmmakers tend to return to the same cinematographers, editors, set designers, casting agents and producers as well. It streamlines the otherwise dangerously obstacle-ridden process of getting what's in your head up on the screen.

At a certain early point in his career, Scorsese looked at Robert De Niro and saw another side of himself: a contemporary who could access psychic depths the filmmaker could only imagine. But in DiCaprio the relationship, negotiated through a 30-year age difference, was more paternal. One imagines the filmmaker didn't see what the kid had inside but what the kid might grow into, even if it took five movies before he grew into it.

Because there's another reason why certain directors have nurtured creative alliances with certain actors: because they see something in them the actor might not yet see themselves, and they trust that the intimacy between them will bring that submerged quality to the surface. Sometimes it takes years: John Ford and John Wayne's working relationship was nearly two decades in by the time Ford so indelibly cast Wayne as the tortured death dealer Ethan Edwards in The Searchers, and it took Akira Kurosawa a full five modern-dress movies before he mined the scruffy samurai spirit in Toshiro Mifune.

So when Martin Scorsese met Leonardo DiCaprio back in 1993, when the actor was barely 19, what did he see? I'm wagering Scorsese saw something in the future: the actor this gifted kid might some day become, perhaps a testament to the trials of spectacular early fame and fortune if the kid wasn't spoiled senseless in the process. An actor smart (and confident) enough to use his own experience to inform the playing of an unrepentant snake, manipulator and sensation-junkie like Jordan Belfort, but mature enough to have himself put some distance between what he was and has become.

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