Leonardo DiCaprio sure loves his period pieces – he’s made about a dozen of them.
With the news that he and Martin Scorsese are developing a biopic about the life of President Teddy Roosevelt, DiCaprio could be poised to explore a new historical period – the early 1900s (Roosevelt was president from 1901-1909).
But this got us thinking, which historical Leo is the best Leo? Is he better as a 1920s jazz age lover, a con man in the 1960s, or a truly evil plantation owner in the 1850s? Do you prefer him as the “King of the World” or the “Wolf of Wall Street?” Whether he’s rocking a tailored three-piece suit or a mountain man beard, he isn’t afraid to lose himself in the trappings of the era he’s inhabiting.
Time travel with Leo below to reflect on his many period roles and then vote for your own favorite historical Leo.
Note: Even though Growing Pains might now seem like a historical capsule of a simpler time, we’ve only included titles that were made in a different era from when they were set. (Same goes for Baz Luhrmann’s contemporary retelling of Romeo + Juliet.)
The Man in the Iron Mask (1660s)
Do you like your Leo longhaired in cravats and floral frock coats? Then The Man in the Iron Mask Leo is the one for you. Even better you get two Leos for the price of one – DiCaprio does double duty as King Louis XIV and Phillippe, his twin brother he’s kept locked away in hiding since birth. So, if you prefer your historical Leo in a white puffy shirt and his face covered by a mask (we see you, Tom Hardy fans), then that’s on tap too. Bonus points for double Leo, but we’re not so sure we’re crazy about the foppish styles of the Sun King.
The Revenant (1820s)
Leo did finally win his Oscar for this one and that’s some definite points in its favor, but his historical look here is mostly frost-bitten fur trapper and unintelligible guttural bellowing. That said, he does wear a bear pelt and hat that is totally 1820s frontier chic.
Django Unchained (1850s)
As plantation owner Calvin Candie, DiCaprio masks a pitch-black soul in an expertly tailored plum colored antebellum suit that exhibits his wealth and “good breeding” down to the white gardenia in his breast pocket.He is frighteningly convincing as an unhinged genteel Southerner, whose perfectly manicured goatee is only matched by the deliberate precision of his cruelty.
Gangs of New York (1860s)
Do you like your Leo hell-bent on revenge with a thick Irish brogue? Gangs of New York’s Amsterdam Vallon might be your favorite then. His 1860s styles pale in comparison to the outlandish suits and top hats of his rival Bill “the Butcher” (Daniel Day-Lewis), but he does have a cool leather newsboy cap. Plus, it’s fun to see Leo with an accent in this Irish immigrant narrative — not to mention, it marked the beginning of a beautiful friendship between him and director Martin Scorsese.
The Quick and the Dead (1880s)
Welcome Leo to the wild, wild West. Here a young DiCaprio is a gunslinger appropriately named “The Kid” who wears a bandana around his neck, a cowboy hat slightly too big for his head, and owns the “gun store” in town. He gets to have some good old-fashioned Western pistol duels, so bonus points for that, but he’s hardly the focal point of the film unlike many of the other roles on this list.
So, to be fair, Jack only has about two costumes in this movie and one of them is a tux he borrows because he’s a stowaway with no luggage. But we still have so much nostalgia (and so many feelings) for this historical Leo. Part of Jack’s appeal is that he isn’t fancy and well put together like the other men in Rose’s life. His working-class attire down to his suspenders and his willingness to roll up his sleeves, whether it’s to dance a jig or talk a woman out of jumping overboard, is exactly what we love about him. This historical Leo might just be the king of our world.
The Great Gatsby (1920s)
We don’t know if there’s anyone else who could pull off a straw boater like Leo does, and he’s got the best white suit in cinema since Humphrey Bogart in Casablanca. Everything Jay Gatsby has may be a carefully constructed lie, but he sure puts on a good show. His shirts are so beautiful they make grown women cry. We raise a glass of champagne to this historical Leo.
J. Edgar (1919-70s)
This one is sort of cheating because J. Edgar spans decades and multiple historical periods. Leo portrays J. Edgar Hoover from young adulthood to deathbed. It’s basically his Citizen Kane, with a similar tale of an idealistic rise to power and a gradual sinking into corruption and lonely secrets. Props to DiCaprio for taking on this massive lifespan, but Hoover might not be likable enough as a character to top this list.
The Aviator (1920s-1940s)
This is another cheat since Leo’s portrayal of Howard Hughes spans from the 1920s to ’40s, but it has more of a sense of continuity because it’s all dominated by the gleam of Hollywood glamour and wealth. DiCaprio delivers a compelling performance with an Errol Flynn worthy mustache and a bevy of impeccable suits. Hughes fashioned himself a larger-than-life figure and at this point, so is Leo – and we can’t deny that he expertly pulls off the classic Hollywood style like the movie star he is.
Shutter Island & Revolutionary Road (1950s)
Leo’s doubled down on his takes on the 1950s, playing both U.S. Marshall Teddy Daniels in Shutter Island and family man Frank Wheeler in Revolutionary Road. Wheeler is the more interesting of the two in terms of capturing the essence of a historical time (Daniels wears the uniform gear of a law enforcement officer and spends much of his screen time in a sterile, frightening mental institution). In Revolutionary Road, DiCaprio perfects the suburban ennui of the man in the gray flannel suit. Plus, he gives fans a long-awaited (if deeply depressing) reunion with Kate Winslet.
Catch Me If You Can (1960s)
As Frank Abagnale, Jr., Leo is a 1960s high school student, doctor, lawyer, pilot, and con man. He cycles through a range of professions in his attempts to forge checks and stay on the run from the FBI, looking slick in his increasingly snappy ensembles. We honestly don’t know if Leo has ever looked better than in all of the 1960s garb for his myriad of professions here. Plus, he gives Tom Hanks a run for his money while doing it. This just might be our favorite historical Leo, and that’s no con.
Wolf of Wall Street (1990s)
Ok, so the 1990s are barely far enough away to count as a “historical Leo,” especially considering he was a working actor throughout the decade. But he has a pretty distinctive look as the smarmy, well-dressed Jordan Belfort – and it captures a very specific historical era of optimism, greed, and economic growth. But Belfort is such a polarizing figure thanks to his womanizing and illegal trading, so it might be hard to name this wolf one of Leo’s best.
Who do you think is the best historical Leo? Vote in our poll below.