Awards: Can Quentin Tarantino Tie Woody Allen for Screenplay Wins?

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Only one person, Woody Allen, has ever won three Oscars for Best Original Screenplay (“Annie Hall,” “Hannah and Her Sisters,” and “Midnight in Paris”). And only one person alive has a chance of matching that total this year. Quentin Tarantino, sitting on two wins in that category (“Pulp Fiction,” “Django Unchained”), could realistically win a third Academy Award in 2020. In the world of the Oscars, asking whether someone “can” win can sometimes seem tautological. Of course, Tarantino can win. We know almost anything can happen at the Oscars. The better question may be: does he have good chances? Six months out, the best answer is, likely, “who knows?”

The Story of Three-Time Screenplay Winners

Allen may be the only screenwriter with three Oscars in the Original Screenplay category, but he sort of has some company. Three screenwriters managed to win two Oscars in this category plus a third in the Best Adapted Screenplay race. They are: Billy Wilder, Paddy Chayefsky, and Charles Brackett. So, regardless of how you slice it, Tarantino would be in rarefied company if he managed the improbable feat.

Tarantino, himself, already has amassed an impressive tally in the Original Screenplay race. His two wins have come out of only three nominations, with “Inglorious Basterds” his only defeat. Indeed, Tarantino converted his very first nomination, for “Pulp Fiction,” into Oscar glory. Chayefsky, who won here for “The Hospital,” and “Network,” lost his first nod in this race. And Allen managed three wins out of a whopping 16 nominations. Those are, of course, impressive, but Tarantino’s winning rate remains even more so.

Tarantino’s Best Original Screenplay Chances for “Once Upon A Time…In Hollywood”

By now, perspective audiences know that Tarantino premiered his ninth film, “Once Upon a Time…In Hollywood,” at the Cannes Film Festival in May. The film hits theaters in the United States this weekend. Generally, the story is a fictionalized look at Hollywood in the late 1960s. Margot Robbie plays actress Sharon Tate. Leonardo DiCaprio and Brad Pitt also star as a washed-up Western actor and his stunt double, respectively.

Oscar races, we believe, are not typically decided on the basis of history alone. Still, context matters. Sometimes, someone being perceived as having “too many” wins can be detrimental. Others, it is a sign of popularity. There is no question in our minds that Tarantino is popular with the Academy. Five of his eight total films so far have received Oscar nominations. Four have won at least one Oscar, and three have even been nominated for Best Picture. Again, the stats speak for themselves. Not everybody likes Tarantino’s style, the violence, or profanity. But enough people in past versions of the Academy clearly do.

Also relevant, of course, is quality. “Death Proof,” Tarantino’s lowest-critically rated film, is one of three of his that earned no Oscar nominations. The other two are “Reservoir Dogs,” a first feature cult-classic, and “Kill Bill,” Tarantino’s third-lowest rated movie. Sitting at a whopping 92% as of the drafting of this article, “Once Upon a Time…In Hollywood,” matches “Pulp Fiction” for Tarantino’s highest-rated film. Disclaimer: I myself gave this movie a negative review and cannot understand what the big fuss is about. Particularly when it comes to the screenplay, in fact. While DiCaprio and Pitt show off their acting chops, and the music is amusing and the set design hammy, the screenplay is the most obnoxious part of what, to me, is an over-indulgent, infantile picture. There seems little “originality” about the screenplay. Tarantino is merely rinsing and repeating some of his old work, and relying heavily on the style of the movies he is purporting to laud and honor.

Lastly, consider the competition. This is where the biggest uncertainty lies and where Tarantino could find himself on the outside looking in unless his movie does stunningly well at the Oscars. While it’s doubtful that Jordan Peele has a realistic chance of getting back to the nominations circle for “Us,” two other film festival movies do have a shot. Mindy Kaling’s “Late Night” and Scott Z. Burns’ “The Report,” both out of Sundance. Each film has at least a decent shot at a nod. So too do unseen pictures that have nevertheless generated early Oscar buzz. That includes A Beautiful Day in the Neighborhood,” the Mr. Rogers biopic with a newly-minted TIFF release, and Harriet,” the biography of the famous abolitionist whose trailer also made a splash recently.

That brings the total to four credible contenders, not to mention Almodovar’s “Pain & Glory,” or Soderbergh’s “The Laundromat.” Competition is not usually this stiff for Best Original Screenplay, but this year could well prove the exception.

All of this is to say that the picture is too muddy at the moment. Does Tarantino have a shot at the fourth nomination in this category? Absolutely. Does he have a chance to tie Woody Allen’s three-peat record? Perhaps, but check back in late January.

Do you think Quentin Tarantino will become the second person to win three Best Original Screenplay Oscars? Tell us below!

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