5 reasons why Brad Pitt could win the Best Supporting Actor Oscar for ‘Once Upon a Time in Hollywood’

As “Once Upon a Time in Hollywood” continues to rake it in at the box office ($100 million and counting), it’s also generating some pretty serious awards conversation – and questions. There’s one in particular that keeps popping up.

Is Brad Pitt leading or supporting? “No decision has been made,” a campaign insider tells Gold Derby. “There’s still a lot of time to see how these races play out.”

Like many, I would argue that he’s a co-lead. He’s clearly part of the central action of the film, and has comparable screen time to the top-billed Leonardo DiCaprio. (Remember, he’s “the king of the world.”) However, Pitt’s frequent onscreen absences would make a supporting campaign less of an outright category crime (see Mahershala Ali in “Green Book” and Alicia Vikander in “The Danish Girl”) and more of an everyday award infraction (think Viola Davis in “Fences” and Patricia Arquette in “Boyhood.”)

In fact, I’m making an early prediction that Pitt will indeed be pushed for supporting. And if he does, we need to keep our eyes on him. (And not for the usual reasons of jealousy or lust.)

Here are five reasons why Brad Pitt could actually win the Best Supporting Actor Oscar for “Once Upon a Time in Hollywood.”

SEE ‘Once Upon a Time in Hollywood’ is an early Oscar front-runner

1. He steals the movie from Leonardo DiCaprio.
This is not meant as an affront to the dynamite DiCaprio, who is exceptional as always. It’s just that while his character Rick Dalton is constantly engaged in tawdry and tedious theatrics, it’s his stunt double Cliff Booth (so perfectly portrayed by Pitt) who inadvertently upstages him. (Caution: spoilers ahead.) Consider the fearless challenge to Bruce Lee on the studio set. Or the raucous wrangle at the Charles Manson ranch. And especially the bloody (and bloody hilarious) home invasion scene near the picture’s end. Many actors might have hammed it up at these key moments, but Brad brilliantly underplays them to a more enchanting effect. His sharp sense of timing, furtive facial expressions and deadpan delivery create what may be the most celebrated showstopper of the year. Ironically, Pitt himself was once overshadowed by a co-star in another Tarantino picture – Christoph Waltz in 2009’s “Inglourious Basterds.” Waltz waltzed off with the Oscar. A decade later, the ingenious Pitt could dance away in similar glory.

2. He’s overdue for the Academy’s recognition.
I know, the overdue factor may not be reason enough. (Just ask Glenn Close.) Still, the twenty-first century has seen a number of unrecognized actors finally prevail after two or more losses. The list includes Julia Roberts in “Erin Brockovich,” Sean Penn in “Mystic River,” Renee Zellweger in “Cold Mountain,” Morgan Freeman in “Million Dollar Baby,” Helen Mirren in “The Queen,” Alan Arkin in “Little Miss Sunshine,” Kate Winslet in “The Reader,” Jeff Bridges in “Crazy Heart,” Julianne Moore in “Still Alice,” DiCaprio in “The Revenant” and Davis in “Fences.” Could Pitt finally make it over the tall Oscar fence? He’s proven himself to be an Academy favorite, earning Best Actor nods for 2008’s “The Curious Case of Benjamin Button” and 2011’s “Moneyball.” He has a long list of credits in other cinematic home runs, such as 1991’s “Thelma and Louise,” 1992’s “A River Runs Through It,” 1999’s “Fight Club,” 2006’s “Babel,” 2008’s “Burn After Reading,” 2011’s “The Tree of Life” and 2013’s Best Picture “12 Years a Slave” (for which he accepted an Oscar for producing.)  Pitt’s first invite to the Academy ball came for his supporting turn in 1995’s “12 Monkeys.” Twenty-four years later, voters may feel that the time is ripe to go bananas for Brad.

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3. He could easily win the Golden Globe.
Once upon a time the Hollywood Foreign Press Association picked Pitt for the prize in “Monkeys,” surprising both the actor and the makers of Kaopectate. (Watch the clip on YouTube if you don’t recall.) Four subsequent nods for acting have been unsuccessful. The HFPA would probably love to see him on stage again. The group tends to reward big stars, and there’s arguably no one bigger than Brad. (Save for his “Hollywood” co-star and three-time Globe champion Leo.) Triumph for Pitt at the season’s first major awards show could spark a chain reaction at the following laurels. Keep reading.

4. He could quite possibly win the SAG Award.
This one’s a bit tricky. SAG members are sometimes lukewarm to matinee idols. (Pitt and pal George Clooney notably both lost the 2011 Outstanding Actor contest to unknown artist – and eventual Oscar winner- Jean Dujardin in “The Artist.”) This year could be different. As I wrote earlier this month, “Once Upon a Time in Hollywood” is very likely to be a strong candidate for Best Cast at SAG. If SAG members fall hard for the film, Pitt could definitely benefit. The group has never individually honored him, despite his impressive resume. Also, remember that Pitt plays a part that most actors can take pity on – a person struggling to survive in show business. SAG voters know that there’s no business like show business – and no one in show business quite like Brad.

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5. “Once Upon a Time in Hollywood” is expected to be a serious threat at the Academy Awards.
Right now, the Tarantino flick leads the Gold Derby odds in the race for Best Picture. It also seems likely to score nominations across the board – in directing, writing, acting and at least a few tech categories. Given the overall support for the film, Academy members will want to reward it somewhere. Should there be stiff competition in the top races, the option of Supporting Actor for Pitt might be the easiest place. That means that “Once Upon a Time” could have a fairy-tale ending for the fairest (and most famous) prince in all of Hollywood.

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Be sure to make your Oscar nominee predictions today so that Hollywood insiders can see how their films and performers are faring in our odds. You can keep changing your predictions as often as you like until just before nominees are announced on January 13. And join in the fun debate over the 2020 Academy Awards taking place right now with Hollywood insiders in our film forums. Read more Gold Derby entertainment news.

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