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What does winning an Oscar even mean anyway?

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A better question to ask than who wins the Oscar: Who benefits the most, win or lose?
Ah, the Oscars. Sunday night’s 96th Academy Awards are the night of a thousand stars and a thousand dreams (hello, Moonlight!) — or heartbreaks, if you’re among the losers (sorry, La La Land). The victorious moment can send a career careening to new heights (hello, Matt Damon and Ben Affleck!) or nudge it in exactly the same direction it was previously headed. (sorry to Mo’Nique.)
Seldom is a career trajectory a straight line; for every Daniel Day-Lewis whose career remains ascendant after their first win, there’s a Leo, whose unforgettable performance didn’t necessarily translate to a career payoff. At times, the overexposure of an Oscar campaign can backfire; actresses like Anne Hathaway and Marisa Tomei have had to suffer through years or even decades of backlash for their Oscar wins. The backlash against Diablo Cody for … writing an Oscar-winning script while being a woman … was so intense that it not only wrecked her career for over a decade, but shut women out of winning the screenwriting category for a full 13 years.
Many of these complicated outcomes boil down to three things that always seem to go hand in hand with the Oscars: sexism, racism, and the toxic combination thereof, misogynoir. Sometimes, though, the Oscars and the subsequent choices of the people who win them are just weird. The ins and outs of Oscar nominations and wins — who gets them, who benefits from getting them, and what happens after you bring home that funny gold statuette — are so complicated that we decided to call in reinforcements to get to the bottom of what it all means. Here, three experts weigh in on what makes the acting Oscars matter, and what the criteria are for a true Oscars success story.
The interviews have been condensed and edited for clarity. Katey Rich, Vanity Fair editor and creator of the podcast Little Gold Men
Do you think an Oscar win has any type of consistency and impact for an actor? I’m not sure that it does.
But those are also people who already had the attention of the industry, who were already on their way to being stars. They’re young, beautiful women. But then you have artists like Mo’Nique — she wins Best Supporting Actress [for Precious], but she had specific ideas of what she wanted her career to be and really wasn’t trying to climb up a ladder as a result of it. I don’t think winning the Oscar had a ton of impact on her career at all, partly because of her choice, and partly because she did not fit the mold.
I think there’s a huge race component to that, but even Melissa Leo had been a character actress for a long time, wins an Oscar for The Fighter, continues being a character actress.
I feel like the supporting category is often reserved for one-hit wonders — which is not to disparage those actors but just to describe how we think about the parts that they play. You can give a supporting actor the kind of quirks that you don’t necessarily get from a lead role. That doesn’t necessarily lend itself to career longevity.
But the winners — I don’t know if it’s a chicken or an egg thing, but the winners can often be more in the “beloved character actor who now gets to be a slightly more beloved character actor” category. Like J.K. Simmons had been “that guy” and then Whiplash [for which Simmons won the Oscar in 2015] breaks him out, and now he’s “that guy” who you recognize but is playing a lot of similar parts. But I bet if you ask J.K. Simmons and his agents, he’s getting paid better. He’s getting better offers. There’s a subtler difference between what you’re seeing as a moviegoer and the differences in their fortunes.

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