Leonardo DiCaprio: The Best Actor to Never Win an Oscar?

Stephen Chernin/AFP/Getty Images

Stephen Chernin/AFP/Getty Images

Actors spend their entire year in the public spotlight, as part of gossip columns, talk shows, and the 24-hour news cycle. The most talented of the bunch get recognized every year at the Academy Awards, where the year’s best get recognized for their considerable efforts. The most coveted award categories (outside of Best Picture) though is by far the ones for Best Actor and Actress. Most every high-profile name structures their year around qualifying for the honor, and there are few actors who embody this more than Leonardo DiCaprio. So why doesn’t he have an Oscar?

It’s certainly not for lack of trying. DiCaprio’s been nominated for Best Actor four times (not counting this year’s nomination for The Revenant), and each year he has lost out to an ill-timed incredible performance by another competitor for the prize. Outside of those four nominations, he’s been in a laundry list full of movies where it’s clear he was angling for an Oscar nod, making it that much more painful to see him lose out on a yearly basis. His resume is chock full of juicy roles he never scored a nomination for, including but not limited to: J. Edgar Hoover in J. Edgar, Frank Wheeler in Revolutionary Road, Billy in The Departed, Amsterdam Vallon in Gangs of New York, Calvin Candle in Django Unchained, and more.

All this lays out the “what” of the situation, so let’s try and dig into the “why” of it all. In chronological order, DiCaprio was nominated for an Oscar for his roles in What’s Eating Gilbert (1994), The Aviator (2005), Blood Diamond (2008), and The Wolf of Wall Street (2013). Each year, a prominent actor swooped in to win the award: In 1994, Leo lost out to Tommy Lee Jones in The Fugitive. 2005 saw him fall to Jamie Foxx’s Ray, 2008 was Forest Whitaker in The Last King of Scotland, and 2014’s Oscars saw none other than Matthew McConaughey take the title for Dallas Buyers Club. 

Each year has been a perfect storm for DiCaprio to find himself trumped, and it’s hard to argue that each respective winner didn’t deserve the award just as much if not more than all other challengers. It’s an unfortunate trend all the same, leaving one of Hollywood’s most accomplished actors with a gaping hole in his trophy case. After taking 2014 off though, he’s returned this year to give it another shot. This time around, he’s assumed a similarly substantial role as legendary frontiersman Hugh Glass, in The Revenant.

The real story of Glass requires little dramatization from Hollywood: Glass’s fellow fur trappers left him for dead with no supplies or weapons, a broken leg, and festering wounds, after he was mauled by a grizzly bear. He then disinfected his own wounds, navigated through hostile Native American territory using only natural landmarks, and somehow made his way 200 miles to the nearest settlement. It’s the sort of story just begging for a skilled touch from an accomplished actor, and it earned DiCaprio his fourth Best Actor nomination.

And while Vegas is putting its faith in DiCaprio finally taking a golden statuette home this year, there’s still a slew of other notable contenders that he will have to beat, including Bryan Cranston in Trumbo, Matt Damon in The Martian, Michael Fassbender in Steve Jobs, and Eddie Redmayne in The Danish Girl. In modern Hollywood, the competition every year is stiff, and this year is no exception. Only time will tell though, as the industry’s most talented actor without an Academy Award continues his quest.

Follow Nick on Twitter @NickNorthwest

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