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Leonardo DiCaprio in Once Upon a Time in Hollywood

Quentin Tarantino had one hell of a morning. His ninth feature film, Once Upon a Time… in Hollywood, scored an impressive 10 Oscar nominations, including Best Picture, Best Director, Best Actor (for Leonardo DiCaprio), Best Supporting Actor (Brad Pit), and Best Original Screenplay. Only Joker nabbed more nominations, with 11, meaning that Tarantino's latest masterpiece will be a major player at the Academy Awards this year.

But did you realize that Tarantino moved one step closer to achieving Hollywood HISTORY this morning?

Let’s explain. For all of his strengths as a filmmaker, Quentin Tarantino seems to take the most pride in his abilities as an original screenwriter. His first Oscar came in 1995, for co-writing Pulp Fiction with Roger Avary. And while he was nominated for Inglourious Basterds in 2010, it took until 2013 for Tarantino to win his second Best Original Screenplay Oscar, this time for Django Unchained.

That win put Tarantino in rarified air. Only four other writers share the distinction of having two or more Oscars for original screenwriting. They are Woody Allen, Charles Brackett, Billy Wilder and Paddy Chayefsky. And only Allen has three wins under his belt with Best Original Screenplay Oscars for Annie Hall, Hannah and Her Sisters, and Midnight in Paris.

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Is this the year that Quentin Tarantino joins Woody Allen in the coveted three-win club?

If he does, it will be impressive for numerous reasons. For starters, Woody Allen has received a record-setting 16 nominations in the Academy’s Original Screenplay category, winning it three times. Tarantino could potentially get his third win on only his fourth attempt. He discussed his screenwriting process during his recent, two-hour conversation with our ReelBlend podcast. If you haven't listened to it yet, press play now.

There’s also a matter of their age. Should Quentin Tarantino win the Best Original Screenplay Oscar for Once Upon a Time… in Hollywood, he will have collected his historic third trophy at the age of 56. Allen, on the other hand, was 77 years old when he received his third screenwriting Oscar for Midnight in Paris in 2012. And he didn’t even show up to accept the Academy Award in person!

So far, Once Upon a Time… in Hollywood is on the right track. It has notched Screenplay wins at the Golden Globes and Critics' Choice (where it also took home Best Picture at the end of the evening), while also being nominated by the BAFTAs and countless regional critics’ organizations. There’s plenty of momentum for the movie, which Sony can dial into and continue to push Tarantino for this potentially historic screenplay win (without taking their eyes off of the larger prizes of Picture and Director, both of which Once Upon a Time… in Hollywood certainly deserves).

So if we had to choose just one, which would you like to see Quentin Tarantino claim on February 9, 2020 at the Academy Awards ceremony? They’ll all be considered historic. All three would be monumental. But vote in our poll, just for fun.

Which Oscar do you REALLY want Tarantino to win?
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