Revisiting The Four Oscar Ceremonies In Which Leonardo DiCaprio Tragically Lost The Gold

Should Leo already have an Oscar? We look back at DiCaprio's losing races and decide whether he was robbed.

Leonardo DiCaprio's struggle to win an Oscar is our modern-day Book of Job. He's Sisyphus rolling a boulder up a hill. He's trapped in Jean-Paul Sartre's hellish world of No Exit. Since the night of March 21, 1994, when he lost Best Supporting Actor to Tommy Lee Jones, Leo has been thirsting for that golden statuette. Now, on the eve of the 88th Annual Academy Awards, for which Leo is nominated for Best Actor in Alejandro G. Iñárritu's The Revenant (and for which he will most likely take home the trophy), let's revisit the four fateful ceremonies in which the Oscar tragically slipped out of Leo's hands and see if, knowing what we know now, he deserved to win any of them.

Paramount Pictures



Leo's Nomination: What's Eating Gilbert Grape

Oscar Winner: Tommy Lee Jones, The Fugitive

The Other Nominees:

Ralph Fiennes, Schindler's List

John Malkovich, In the Line of Fire

Pete Postlethwaite, In the Name of the Father

After a few appearances in iconic films like Poison Ivy and Critters 3, Leo fired shots as a major Hollywood player in the making with his turn as the developmentally disabled Arnie, brother to Johnny Depp's Gilbert in 1992's What's Eating Gilbert Grape. The film, awarded four stars by Roger Ebert at the time, oddly received no other Oscar nominations despite Depp and Mary Steenburgen turning on some of the best work of their careers. The film itself hasn't stood the test of time as far as a cultural milestone, aside from Leo's nomination. It's certainly a fine, well-made film. But it's easier to see why Leonardo would have lost to Ralph Fiennes in a flashier, still-referenced film like Schindler's List ... except he didn't. He lost to Tommy Lee Jones in The Fugitive.

Look, The Fugitive is a fine movie. But if you're awarding Jones an Oscar for that, there's no reason Ashley Judd shouldn't have one for Double Jeopardy. This was clearly a case of awarding Jones the Oscar he didn't get two years earlier for JFK. (Jack Palance won that year for City Slickers. Um, what?) John Malkovich and Pete Postlethwaite are great actors, obviously, but their two movies with similar-sounding names have been mostly lost to time. Who remembers any of these, except for maybe Daniel Day Lewis's In the Name of the Father performance? Even then, Lewis lost to Tom Hanks for his role in Philadelphia — an Oscar that should've gone to Laurence Fishburne for What's Love Got to Do With It, the second injustice of the night. (The first obviously being that Angela Fucking Bassett didn't win for What's Love Got to Do With It and Holly Hunter did for The Piano, BUT I DIGRESS.)

Leo's only real competition this year should've been Fiennes. Still, I think Leo should've taken this one home.




Leo's Nomination: The Aviator

Oscar Winner: Jamie Foxx, Ray

The Other Nominees:

Don Cheadle, Hotel Rwanda

Johnny Depp, Finding Neverland

Clint Eastwood, Million Dollar Baby

2005 was one of the years the Academy remembered black people exist. Jamie Foxx won for Ray. Morgan Freeman won for Million Dollar Baby. Foxx was nominated a second time for Collateral. Don Cheadle got a nomination for Hotel Rwanda. Don't worry, they made up for it the next year by awarding Best Picture to Crash, a terrible movie about race. But during 2005, it was like Gangsta's Paradise up in the Oscars. Leo didn't stand a chance. But should he have?

Short answer: Not really. The Aviator is a pretty great movie. It's long as fuuuuuuuck, but it's still pretty dope. The reason why it didn't win Best Picture, however, rests on Leo's shoulders. He was really too young to be playing Howard Hughes, for one. Watching it now, it operates more like a dry run for his portrayal of Jay Gatsby nine years later. But here, he's a bit like a freshman who got a lead role in the school play opposite a graduating senior. Cate Blanchett acts circles around Leo (as Hughes's onetime lover Katharine Hepburn) and picked up an Oscar for her trouble. Second, Leo's accent is ATROCIOUS. It's not his worst film accent ever (that one's coming up next), but it's certainly not good, either. If Some Like It Hot were set in Texas, you still couldn't come up with whatever combination of Roaring-'20s-meets-fast-talking-country-boy accent Leo was attempting. By the time Hughes is an aged eccentric pissing in jars, you end up wishing they'd just recast the older version.

As good as everyone else in the category was, Foxx pretty much disappeared into his role as Ray Charles. It's his greatest performance and every bit worthy of the Oscar — if only because Tom Cruise wasn't nominated for Collateral, a movie for which they both could've won awards if the Academy had given Foxx Best Supporting Actor instead of Best Actor.

Warner Bros.



Leo's Nomination: Blood Diamond

Oscar Winner: Forest Whitaker, The Last King of Scotland

The Other Nominees:

Ryan Gosling, Half Nelson

Peter O'Toole, Venus

Will Smith, The Pursuit of Happyness

As I already mentioned, this is the worst accent to ever escape Leo's lips. He's supposed to be South African in Blood Diamond, but I'll be damned if that's what he's doing here with his voice. It's some odd combination of French and British and Leo, What the Fuck Are You Doing, Stop Doing Movies Where You Have To Do Accents. The accent, however, is hardly the worst part of this movie; the movie is the worst part of this movie. Blood Diamond is not good. In fact, I would go so far as to suggest that it is a bad film, with dialogue from screenwriter Charles Leavitt like "You know, in America it's bling bling, but out here it's bling bang." But what did you expect when two white people (Leavitt and director Edward Zwick) team up to make a movie about the diamond trade in Africa and cast Leonardo DiCaprio as a South African?

If even Djimon Hounsou couldn't win for his supporting role in this film, there was no way Leo was going to win. Especially considering his competition: He could've easily trounced Ryan Gosling, sure, back when Hollywood was actually in love with him. (Leo seems to have been largely forgotten at this point. And Half Nelson may actually be Gosling's best performance, even if it is a bit too Dangerous Minds for my liking. He could've beat Will Smith as well, because I was surprised to find out that Tyler Perry wasn't responsible for the general mess that is The Pursuit of Happyness. I don't recall anything about Venus and I've seen Venus, so it's safe to assume it wasn't one of Peter O'Toole's most memorable performances. No, Forest Whitaker had this in the bag. His performance in (the otherwise underwhelming) The Last King of Scotland was a tour de force. He earned that golden statuette.



Leo's Nomination: The Wolf of Wall Street

Oscar Winner: Matthew McConaughey, Dallas Buyers Club

The Other Nominees:

Christian Bale, American Hustle

Bruce Dern, Nebraska

Chiwetel Ejiofor, 12 Years a Slave

Is anyone still talking about Dallas Buyers Club? This movie dominated the awards-season conversation leading up to the 2014 ceremony, but does anyone remember it fondly? (Besides Jared Leto fans, because he also won this year for his portrayal of a trans woman.) Other problems in this category include any nomination for American Hustle, which should've been the first David O. Russell film shut out of the Oscars before people wised up and said "nah" to Joy this year.

Bruce Dern is great, but Nebraska is in black-and-white and I won't abide that nonsense. Leo's real competition here should've been Chiwetel Ejiofor in 12 Years a Slave. It's oddly surprising he didn't win, actually, but that's just about how much the McConaughey campaign was working overtime. Hollywood usually bends over backward to award a golden statue to a black man who gets whipped and called the n-word for 70 percent of a film (Samuel L. Jackson sadly did not get whipped in The Hateful Eight, so he got no nomination this year). Ejiofor's performance is powerful and moving, but I am of the opinion that we should not reward black actors for handing over a pound of flesh. Though 12 Years is incredibly important -- and very necessary since white people keep forgetting slavery existed until we remind them (then we're talking about it too much!) -- I would rather Chiwetel win an Oscar for a film like The Wolf of Wall Street. Leo fully transformed into a MOVIE STAR with this role. Exuberant, joyful, and living in every bit of pulp Martin Scorsese infused into the film, this is a role we'll remember for years to come. If he didn't win for Gilbert Grape, this should've been Leo's Oscar moment.

What's Eating Gilbert Grape and The Wolf of Wall Street were definite awards oversights for Leo — but there’s actually an even bigger one. Sure, maybe he should've been nominated for The Basketball Diaries, Catch Me If You Can, and The Departed. There might even be a case to be made for Titanic. But this is utter insanity...


Leo should've gotten Best Supporting Actor in 2013 for Django Unchained. Yes, Christoph Waltz was great, but he was much better in Inglourious Basterds. Leo was the true star of Django, with his wickedly fun turn as the evil Calvin Candie, but the role earned him only a Golden Globe nom, not an Oscar nod. Instead, the Academy played some real games with their nominations that year — Tommy Lee Jones for Lincoln? Why is he always taking my man Leo's spot?

All Leo's life he's had to fight. He's had to fight Tommy Lee Jones. He's had to fight Jamie Foxx. He's had to fight Forest Whitaker. He's had to fight Matthew McConaughey. And now, goddamit, even if it's for The Revenant — he's got to win.

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