Last night, as The Boy Who Won stood onstage to thank a bunch of strangers for giving him a new piece of guest bathroom decor, the main duty of his right hand was to clutch the Oscar statue. To hold it tight. To begin a lifetime of cherishing. But while four of Leo’s digits held the little gold man, his middle finger clutched the envelope that held his name. Some have interpreted this as an official shooting of the bird—a middle finger at the Academy.

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But was he merely displaying a middle finger, or was he giving one? And if it was the latter, who was its intended recipient? As Jezebel’s resident Finger, I feel more than qualified to interpret the actions of Leo’s.

I. A Finger or the Finger?

First, let’s talk about that envelope. Whether or not it’s held along with the statue is entirely up to the winner. Most actors, like last night’s winners, just leave it with the presenter.

Brie, Mark, and Alicia had more important things to carry.

Some, like Octavia Spencer, take the Leo route and hold both.

But take a closer look at the hierarchy of that hold. Spencer kept the statue front and center, as one should, and placed the envelope below it. This seems like the obvious choice, does it not? You just won an OSCAR and want to show it to EVERYONE. Like this guy. The man may not know what movie he was responsible for or how he made it to the stage without falling, but he knows how to hold an Oscar and an envelope.

To those who say, “Maybe he didn’t know he could leave it with the presenter! Maybe he was overwhelmed by the moment and wasn’t thinking about the envelope obstructing his Oscar!” allow me to remind you that Leo has spent the better part of 20 years narrowly missing an Oscar win and/or nomination, and his win this year was all but guaranteed. Dude knew he was going up there, and had been to enough Oscars ceremonies to know the drill. His exposed middle finger was the result of two conscious decisions:

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  1. The decision to grab the envelope from Julianne Moore.
  2. The decision to hold in in front of the statue as opposed to underneath it.

For those reasons, I’m confident his middle finger was, in fact, given. But now the question remains: to whom?

II. The Academy Assumption

The easy answer to this is, “He was flipping off the Academy!” But I’m not so sure that’s the case. Think about it, Leo was doing fine without an Academy Award. He kept getting good roles, and he kept pulling in audiences. At his core, Leo is just a good, famous actor who loves the environment, hanging with his boys (the Pussy Posse), and having sex with models. As Susan Lucci proved in the ’90s, a string of near-wins can do more to improve your level of fame than the win itself, and Leo’s constant losses were probably the most notable thing about him.

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The Academy arguably did his career his career a favor by waiting so many years to blow their golden load, so why would he shoot them the bird? Couple that with the fact that it would be pretty petty to be begrudge them for his comparably minor “injustice” in the same year they’re being rightfully confronted with their history of bigger failures (failures he did not bring up in his speech), and I feel confident assuming Leo’s target wasn’t the A.M.P.A.S.

So. Allow me to go out on a limb.

III. This Finger’s Theory

Let’s talk feuds. Does Leonardo DiCaprio have any active ones?

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Though his gasp at Lady Gaga during the Golden Globes was widely reported as shade, I believe his explanation for the reaction: “I didn’t know what was passing me—that’s all!” No feud there.

Did he have any reason to be mad at his fellow nominees for Best Actor? I couldn’t find any bad blood with Cranston, Redmayne, or Fassbender, so they’re out. This old Instagram claims he was once heard “talking shit” about nominee Matt Damon, but shit talk does not equal a finger-worthy feud. I’m sure Leo has talked shit about half the people in the audience last night.

Where does that leave us? I’ll tell you where it leads us.

That’s fucking right, motherfuckers. It leads us right to the motherfucking Pussy Posse. I believe that long ago, when the Pussy Posse (which includes Leo, Lukas Haas, Tobey Maguire, David Blaine and Kevin Connolly) was still young and wreaking havoc on New York City, the actors made a bet.

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“The first one of us to ever win an Oscar,” I imagine Leo saying at around 4:00AM on a Monday morning, “has to fuckin’ flip off the camera.” Everyone but Leo laughs. “I’m fuckin’ serious. Promise me. Promise me right now that if one of us ever goes up there, we do it. For the posse.”

The young men get silent, think for a moment, and clasp all their middle fingers together.

“For the posse.”

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It took longer than any of them expected, but they finally fuckin’ did it.


Contact the author at bobby@jezebel.com.

Images via Getty, GIF by our staff Finger