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DiCaprio, born in 1974, is now nearing 50, and his role in Killers is perhaps the first one in which he looks truly middle-aged: as Ernest, he’s arranged his mouth into a permanent half-moon frown—it’s an affect that makes his performance seem a little forced, though he manages to navigate Ernest’s emotional turmoil gracefully enough. Ernest is a not-very-bright man who loves money—he states it both plainly and indirectly, in scene after scene—but he also loves the wife whom his uncle has half-persuaded him to kill; the conflict between his love and the tragic duty with which he’s been entrusted plays out in the moral cloudiness of his eyes. DiCaprio and De Niro have worked together twice before, most recently in Jerry Zak’s 2016 Marvin’s Room. But it was This Boy’s Life that led directly to DiCaprio’s status as one of Scorsese’s signature actors: in that movie, De Niro played the bullying stepfather Dwight—nemesis of DiCaprio’s wayward teenager Toby—and was so impressed with his young co-star that he urged his longtime collaborator Scorsese to consider working with him.
The Scorsese–DiCaprio partnership has yielded six films, beginning with 2002’s Gangs of New York, a folk-tale history of old Manhattan, in which DiCaprio played Amsterdam, an orphan out for vengeance against neighborhood kingpin Bill the Butcher, played by Daniel Day-Lewis. DiCaprio has done good work with Scorsese—he was entertaining as the crooked highflying investment god Jordan Belfort in The Wolf of Wall Street—but his turn as the young Howard Hughes, in The Aviator, is my favorite of the Scorsese–DiCaprio collaborations. The Aviator unapologetically romanticizes Hughes, an engineer, movie mogul, pilot, and very weird guy, downplaying his paranoia and cruelty. DiCaprio lends his version of Hughes a touching strangeness. He’s more handsome than Hughes ever was; his eyes sometimes look inhumanly blue, like the designs on a Delft plate. DiCaprio plays Hughes in the era before he entered the realm of true madness, though his eccentricities, anxieties, and compulsions had already begun to rule him. In two scenes, he’s barricaded himself off from the world, in need of rescue; in each case, an old girlfriend (one is Cate Blanchett’s Katharine Hepburn, the other Kate Beckinsale’s Ava Gardner) steps in to help. He presents Hughes’ gratitude toward each as a kind of confused tenderness. The real Howard Hughes was a piece of work, and a mess. But DiCaprio embodies him as a complex human being deserving not just of our curiosity but also our sympathy.
As an actor, DiCaprio earned the top-tier director’s seal of approval early on, having been sought out not only through Scorsese but also through Christopher Nolan (Inception), Steven Spielberg (Catch Me If You Can), Clint Eastwood (J . Edgar ). Array and Quentin Tarantino (Django Unchained and Once Upon a Time in Hollywood). Not all of those performances are great: In J. Edgar, in particular, DiCaprio had the unenviable task of portraying a delicate portrait of J. Edgar Hoover, a vile little man. But more than anything, DiCaprio wins with his charm, as a warm-hearted con man in Catch Me If You Can, or as fictional TV star Rick Dalton in Once Upon a Time in Hollywood. And he fits best as the dazzling centerpiece of Baz Lurhrmann’s bead-fringed spectacle, The Great Gatsthrough. Luhrmann’s adaptation is disliked by those who see F. Scott Fitzgerald’s novel as a scolding story about the risks of having too much money. But it’s less an adaptation of Fitzgerald’s novel than a film edition of Jay Gats himself, a character with the glittering allure of a gold pocket watch set with diamonds. DiCaprio plays Gatsthrough as a self-invented charm czar in an art deco tuxedo, capturing the artificiality of the character’s silk tie as well as his damned loneliness. He brings a brooding glamor to this absolutely over-the-top film.
DiCaprio is even older in the last film he directed with Luhrmann, as the love fiancé in 1996’s passionately romantic Romeo Juliet: with Claire Danes’ Juliet as the object of his amorous gaze, he’s the ultimate young tragedian, oh so handsome. That shines like the evening light. It’s one of two videos that turned DiCaprio into a teen idol of the 1990s; the other is James Cameron’s Titanic (1997), a film of enduring popularity that is truly, if you look at it with a modicum of critical discernment, a mixture overloaded with sentimentality and technical genius. That said, when Titanic did, DiCaprio and his partner-star Kate Winslet were two of the most beautiful beings on the planet. Its brilliance endures even when the film drags on.
Which brings us, in our time machine, nearly back to 1993, and the two roles that kicked off DiCaprio’s ascent. In 1993, he looked younger than his age at the time, 19. His reedy build suggested preteen lankiness; his complexion seemed to have the texture of silk onscreen, as if it had never seen a day of acne. He was the ideal actor to play Arnie Grape in Lasse Hallström’s What’s Eating Gilbert Grape, the needy but eternally innocent younger brother to Johnny Depp’s beleaguered, protective Gilbert. Hallström’s filmmaking style here has that slightly glossy veneer that makes so many films of the late 1980s and early 1990s feel overworked and vaguely artificial. But that doesn’t mar work that Depp and DiCaprio, both superb, do here.
It’s hard to say if anyone would make a movie like Gilbert Grape today; its depiction of a disabled teenager as an eternal dependent could be seen as pitying. But the truthfulness of DiCaprio’s performance, and his insistence on preserving the character’s dignity, felt fresh and revolutionary at the time, and it’s still remarkable today. He captures Arnie’s windmilling joy, but also his semi-awareness that the world has somehow left him behind. And as Toby in This Boy’s Life—a stand-in for Tobias Wolff, on whose memoir the movie was based—DiCaprio walks the slender line between being a too-much-for-everyone bratty teenager and a fatherless kid who’s merely trying to swagger his way out of his own sadness. It’s easy to look at this performance today—to take the measure of those youthful, chiseled cheekbones, and those eyes capable of shifting from calculating to crestfallen in a millisecond—and claim to see DiCaprio’s destiny as a star. But life and fame don’t always follow a predictable trajectory. To watch these wonderful, youthful performances is to see the ghostly outline of a great future career. That DiCaprio actually brought it to life, and continues to keep it whirring 30 years later, is the kind of Hollywood story you wouldn’t dare invent. It’s a dream we saw coming, and for once, we were actually right.
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