Revisiting Leonardo DiCaprio's Oscar-Losing Faces

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In all likelihood, Leonardo DiCaprio will win his first Academy Award this weekend for his beard-growing and bear-fighting performance in The Revenant. He will walk up those steps, make a tastefully triumphant speech, hold the little gold man in his hands, and get whisked away to a tropical paradise populated by models half his age. As the awards-season narrative demands, his whole career has been building to this point. It's his destiny.

But, as beautiful as that moment will be, it will also be sad. Why? Because it will break the streak of Leo's dignity-filled Oscar losses. Say goodbye to the GIFs and the memes. To celebrate this end of an era, two of our writers and Leo lovers, Dan Jackson and Anna Silman, dug deep into the the actor's Oscar-losing faces. As the poster for The Revenant says, "Blood lost. Life found."

The year: 1994
Nominated for: What's Eating Gilbert Grape
Lost to: Tommy Lee Jones for The Fugitive

Anna: Aww, young Leo! He's only a wee lad here, so I feel like he was probably just happy to be nominated. Plus, he got to meet Ralph Fiennes, which is like every young boy's dream. Teens love Ralph Fiennes, right?

Dan: Yeah, there's nothing a sweet-faced little 10-year-old child star likes more than rubbing elbows with Amon Goeth from Schindler's List. Oh, wait, I just looked it up and Leo was actually 19 when this ceremony happened. He looks so... fresh-faced, like there's nothing this little dude wants more than to go home and play with his Nintendo Power Glove.

Do you think Tommy Lee Jones let Leo touch the Oscar at the afterparty? And, like, where was John Malkovich?

Anna: Malkovich clearly gives no fucks about the Academy. Unlike Leo, who’s just thrilled to be there basking in this once-in-a-lifetime honor that will almost certainly never happen again. Ah, young Leo. So naive. I bet he doesn't even vape yet. Did people vape in 1994?

Dan: It wouldn't surprise me if Leo was in on the early beta testing for the vaporizer. He's THAT COOL!

The year: 2005
Nominated for: The Aviator
Lost to: Jamie Foxx for Ray

Dan: Look at that serious man! Let's break down that reaction: sternly clapping, fingers rigid in a little tipi of slowly simmering rage, eyes cast towards the stage like he's eyeing some Titanic-hating chump dancing with his girl from across the Viper Room.

Leo is too good of an actor to let you know that he's pissed. But you can tell this bullshit is starting to weigh him down. Jamie Foxx may have imitated Ray Charles, but Leo was Howard Hughes? How dare they, Anna? How dare they?

Anna: I share in your outrage, Dan.

Leo's trying to look casual, but he's clearly annoyed. He urinated in bottles for this shit! Do you even KNOW how many jugs of homogenized milk he had to drink every day to prepare for this role? The more I gaze into Leo's vacant, thousand-yard stare, I’m starting to think that all that method acting might have gone to his head. I feel like his inner monologue is just "the way of the future, the way of the future, the way of the future, the way of the future."

Dan: "The way of the future. The way of the future. The way of the future." Sorry, got distracted there. I'm writing this from my personal screening room where I watch this Leo-starring Kraft Singles commercial on a constant loop. Weird to think of how important dairy has been to Leo's whole career arc.

Anyway, speaking of the future, what do you think Leo did after the ceremony? This happened in 2006, so do you think he listened to Daniel Powter's "Bad Day" after losing or was he more of a "You're Beautiful" guy?

Anna: Come on, Leo does not listen to James Blunt, even during his post-Oscar sulk sessions. He and Gisele probably went home and had an epic bone-sesh while rapping along to The Black Album. At least that's what I like to imagine. In fact, I'm imagining it right now. Give me a minute.

The year: 2007
Nominated for:Blood Diamond
Lost to: Forest Whitaker for The Last King of Scotland

Dan: Leo, my man! Good job keeping your cool. Two years have passed since his Aviator defeat, but you can already tell Leo has perfected the art of losing: stare off vacantly, golf-clap really fast, then swivel your head to the side so you can say something to your date, like, "Thank God I didn't lose to Ryan Gosling for Half Nelson. That would've been humiliating." Besides, I don't even think Leo thought he would win for Blood Diamond. That movie was trash, right?

Anna: Definitely not his best work. I agree that he looks more believably nonchalant here than he did in ‘05, but he’s definitely got a bit of a tense jaw-clench situation going on. Maybe he's trying to stop himself from blurting out some heinous South African swear word he picked up on set.

Dan: You're right! He looks like he might shit in his tuxedo pants in anticipation. You think anyone has ever done that at the Oscars? A theory: that's why John Malkovich wasn't on screen for the nomination part in 1994.

Anna: You are definitely wrong. And Leo even gave Forest a standing ovation here -- classy DiCaprio deserves applause of his own! Moving on...

The year: 2014
Nominated for:The Wolf of Wall Street
Lost to: Matthew McConaughey for Dallas Buyers Club

Anna: You've gotta give Leo credit: even as he suffers through his fourth upset, he's still the picture of composure, pulling an immediate deferential clap-and-swivel towards his Wolf of Wall Street co-star McConaughey (who he apparently doesn't love), and then even giving him a bro-smooch and -hug. Ugh, and then he has to sit through McConaughey's insufferable Rust Cohle gibberish speech. The Oscars are a flat circle.

Dan: Whoa, I don't like all this McConaughey hate. My heart is big enough for both these gold-statue-coveting beefcakes. It's possible to play the bongos and balance a G-pen between your lips. I don't want to live in a world where I have to choose between the star of Surfer, Dude (yes, the comma is real -- I checked) and the star of The Beach.

One thing I just noticed, Leo went back to the bow tie this year? You think he wears a bow tie again this Sunday?

Anna: Excuse me Dan, you can’t just slander me as a McConaughater and then expect me to move on to discussion of neckties.

For the RECORD, I dig Hollywood's resident Surfer-comma-dude as much as the next gal, I just think his speech was kinda bullshit and I would much rather hear Leo waxing poetic about the plight of indigenous communities/the scourge of capitalism/how to minimize our carbon footprints than have Matty Mac trying to explain that "when you got God, you got a friend. And that friend is you." Like, what? No.

And yes, of course Leo’s gonna wear a bow tie this year. He's gotta look sharp for when he finally gets his statue (although really, when does he not?)

Dan: I'm glad we're on the same page. DiCaprio usually does look pretty sharp. But the one thing I can't stop thinking about is this: what if he loses on Sunday? What if he has to do the clenched-jaw clapping thing one more time? What if he's destined to chase this absurd little gold statue for years like his Revenant character goes after Tom Hardy? I could see the Dolby Theatre ending in a bloodbath on Sunday night.

And, even darker, what if we're destined to write blog posts like this forever? I don't have any more vape jokes.

Anna: A world where Leo loses for a fifth time is not a world I want to live in. If that happens, bury me alive and leave my body for the bears, please.

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