Leonardo DiCaprio’s Most Incredible Characters


Last fall we learned that Leonardo DiCaprio and Martin Scorsese would be teaming up once again to create a film that will no doubt be the talk of Hollywood when it’s finally released. This time around it’s Devil In The White City, an adaptation of Erik Larson’s novel about the 1893 Chicago World’s Fair and the infamous serial killer who plagued it. DiCaprio will reportedly be assuming the role of Dr. H. H. Holmes (the serial killer) in what could be one of his most fascinating character projects yet.

Most agree by this point that DiCaprio is among the more talented and accomplished actors in Hollywood, and it’s probably both a cause and a result of this that’s led him to play an amazing array of characters over the years. Those who have read Larson’s work will be expecting a villain for the ages when this next film surfaces, but in the meantime let’s take a look back. Not necessarily at Leo’s best performances, but at the most amazing people he’s played when he’s delved into history and literature.

Hugh Glass

Playing the part of Hugh Glass in The Revenant finally earned DiCaprio his elusive Oscar for Best Actor earlier this year. While it was hard not to be impressed with DiCaprio’s gritty, committed performance, the real life Glass was a character so much larger than life that it’s probably impossible to get a fully accurate idea of him from film. Yes, he was mauled by a bear on the American frontier and left for dead by his company, prompting him to undertake a quest for vengeance while barely clinging to life—but Glass had a whole life of adventure, worthy of a full series of movies, that didn’t make the cut for The Revenant.

You can read a fuller account in the book upon which the film was based, or in a number of Hugh Glass biographies that have been published. But True West, a sort of online magazine that professes to tell the history of the American frontier with its publications, also has a detailed account of Glass’s life that delves into his history as a sailor who was captured by an infamous pirate. Glass himself ultimately became a pirate, and in the process learned many of his survival skills and obtained the special gun that would later be stolen from him after the grizzly bear incident (something that was played down slightly in the film). Simply put, this guy had a wildly improbable and wholly adventurous life.

Howard Hughes

You may remember The Aviator as the long and dramatic 2004 film that earned DiCaprio his first nomination for Best Actor at the Oscars (he’s since been nominated three more times, including his win for The Revenant). It was a massive project, directed by Scorsese, spanning 170 minutes, and aimed unmistakably at the committees that decide awards. But if anything, DiCaprio dove so fully into the personal character of Howard Hughes, the film’s subject, that Hughes’s life itself was a little bit overshadowed.

As a reminder, this is a man who was simultaneously one of the wealthiest businessmen in America in the first half of the 20th century, a pioneering filmmaker, and a record setting aerospace engineer. He made numerous films (including the original Scarface), set new standards for air speed, and grew Trans World Airlines into a massive company that would later become American Airlines. The Aviator touched on a lot of these accomplishments, but it was largely a psychological examination of Hughes, who grew paranoid with each new success he had.

Jay Gatsby

Gatsby isn’t a real life person like Glass (whose life may well have been partially mythologized) or Hughes. But he’s arguably the most iconic character in American literature, and it fell to DiCaprio to play him in Baz Luhrmann’s eccentric but intoxicating 2013 film, The Great Gatsby. As with Hughes, DiCaprio focused largely on the psychology beneath the shine of Gatsby, though in this case that’s an intended focus of the original work; Gatsby is a mysterious man with deep motivations and questionable legitimacy, as sad as he is boisterous, and DiCaprio captured all of this rather well.

But the character from literature is truly a marvel. It’s a little more difficult to analyze a fully fictional persona, but for one thing it’s worth noting that Gatsby is considered to be one of the richest fictional characters of all time. This was determined in a fun little article posted by Lottoland, which is better known for its roulette games and lottery selections. Naturally, those playing such games enjoy hearing about the super-rich, and Gatsby certainly qualifies. And that’s what really speaks to what makes him such an amazing character. He’s a man who more or less came from nothing to assume a new identity and embark on a life-long con, turning himself into an unrivaled success all in the name of impressing an ex-lover.

J. Edgar Hoover

DiCaprio’s portrayal of the infamous FBI director J. Edgar Hoover may have been his most polarizing role, at least in terms of playing real figures from literature or history. Reviews for the performance ranged from calling it “undeniably terrific” and citing DiCaprio as “our most underappreciated major actor” to saying that it was “elusive” for DiCaprio to uncover the man he was attempting to play, or that his “eyes were a little too feline” for the role. In short, people had opinions all across the board for this one.

But that may ultimately be fitting when you consider that Hoover himself is something of a polarizing figure in history. On the one hand, he’s largely credited with turning the FBI into what we know it as today, and without his dedication we might not have the federal investigation force we have in the United States. On the other hand, the latter stages of his career were marked by allegations of misconduct and abuses of power so extreme that President Truman compared Hoover’s FBI to the Gestapo!

It will be fascinating to see where DiCaprio’s role in Devil in the White City will fit on this list. While horrible, Dr. H. H. Holmes is every bit as fascinating as these other characters that have marked the actor’s career.

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2 thoughts on “Leonardo DiCaprio’s Most Incredible Characters

  1. Interesting approach to the career of one of our great actors. I've yet to see The Revenant, but plan on doing so in the next few days. The rest of these are indeed incredible people, and the fictional Gatsby is rightfully included. I'm among the folks who think J. Edgar was a horrible film. Di Caprio's performance was pretty good, but nowhere near what it could have been if the material were better. Great post.
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