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Five Films Featuring Leonardo DiCaprio You Should Check Out Before Seeing Once Upon A Time…In Hollywood

With so many movies to his resume, it’s hard to single out only five that are essential in tracing the arc of Leonardo DiCaprio’s acting career up to his latest film, Quentin Tarantino’s Once Upon A Time…In Hollywood. Consider this a very abridged primer then, a starting point for an actor who is one of the very best, if not the best, of his generation.

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THIS BOY’S LIFE (1993)

Director Michael Caton-Jones effectively introduced a young Leonardo DiCaprio to movie-going audiences in what arguably was the best coming of age performance anyone had seen since River Phoenix’s breakout performance in 1986’s Stand By Me. In a film that dealt with tough issues such as physical and mental abuse, DiCaprio came out of the gates swinging, delivering a rare performance for an actor of any age. Not many actors would be able to hold their own against powerhouse Robert DeNiro, yet the still teenaged DiCaprio goes toe to toe with the maestro and walks out of this film a winner. The Oscar nomination he snagged for his follow-up film later that same year, What’s Eating Gilbert Grape, only validated what anyone who saw This Boy’s Life already knew: This was an actor to watch.

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CELEBRITY (1998)

After the pop cultural phenomenon that was James Cameron’s Titanic (1997), where was any self-respecting Indy darling/thespian to turn to remind connoisseurs of his earlier, smaller work (think The Basketball Diaries, Total Eclipse and Marvin’s Room) that the biggest blockbuster in the history of moviedom aside, he could still act with the best of them? Enter Mister Woody Allen and his otherwise forgettable film, Celebrity. DiCaprio shows up about halfway into Allen’s study of the disastrous career and questionable private life of a writer (Kenneth Branagh) and interjects an atomic blast into an otherwise slumbering story with his portrayal of a coked out edgy movie star who wants nothing more than to conquer in and out of the bedroom. Too bad that his screen time is limited to about ten minutes of actual film, but it’s a ten minutes that captivates as DiCaprio does a fun sendup of a hotel trashing and indecisive actor. Not since Christopher Walken’s brief cameo in Allen’s Annie Hall has so little left you wanting so much more.

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THE AVIATOR (2004)

A lot of people think that Leonardo DiCaprio’s career became a thing of potential legend with his nearly unprecedented five (soon to be six) picture collaboration with master filmmaker Martin Scorsese. They would be right on the money with this assessment as the heir apparent to such acting giants as Montgomery Clift and Marlon Brando seemed to do his best work in tandem with Scorsese. Although their first effort together – Gangs of New York – was a noble failure, it was with their sophomore outing about eccentric millionaire Howard Hughes that they began hitting their stride and it paid off for the actor as he hit acting notes heretofore unknown in his bravura performance and walked away with his second Oscar nomination.

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SHUTTER ISLAND (2010)

Although many cite DiCaprio’s and Scorsese’s third outing together – The Departed – as their favorite amongst all of their film work together, it’s really with Shutter Island that the two seemed to reach a zenith. Presented as a murder mystery whodunnit, what this film is really all about is loss and the sometimes terriable things we do to ourselves to shield ourselves from pain that is so great it threatens to capsize our entire being. And DiCaprio is playing at a master’s level here, at once stoic and hardheaded in the best gumshoe tradition and on the other hand excruciatingly vulnerable and teetering on the brink of an emotional abyss that is profound. His performance was criminally overlooked during awards season, alas, but look for the lustre of Scorsese’s masterpiece to only grow in the years ahead as twenty years from now we all ask in unison “How did this brilliant film with such a brilliant performance by its leading man get largely overlooked?”

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THE GREAT GATSBY (2013)

“To the manor born” they say when referring to someone who is destined to something by birthright and I frankly cannot think of a more apt phrase for DiCaprio’s turn as one of literature’s greatest characters, Jay Gatsby, a self-made millionaire who wants for all the world to be accepted and loved. Perhaps because of that universal sentiment that we all share, DiCaprio is beyond reproach in this his second film with director Baz Luhrmann, The Great Gatsby. The actor brings a surprising empathy to his performance that is captivating and, though most of us know F. Scott Fitzgerald’s pre-Depression era cautionary tale well, it is through the good graces of Luhrmann and DiCaprio that the story seems cleaned up and shiny-new. The director uses some of his effective tricks to showcase why the story transposed is relevant to any time and place (a device he used masterfully in his first turn with DiCaprio, Romeo and Juliet) but it’s really DiCaprio the audience is anxious to see and it’s fun to watch him make choices onscreen that seem to, in some ways, mirror his own existence as what The Hollywood Reporter has rightly dubbed “the last movie star.”

About Ryan Vandergriff

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