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Oscars: Will Leonardo DiCaprio and Brad Pitt Face Off in Best Actor Category?

With red-hot pairings like Leonardo DiCaprio and Brad Pitt, this year’s awards season could again face a classic Hollywood dilemma: Which high-profile actors are the leads and which are supporting?

Last year, Olivia Colman upset Glenn Close to win the Oscar for best actress, but truth be told, Colman wasn’t the sole lead of “The Favourite.” The film was a three-hander with Emma Stone and Rachel Weisz as Colman’s big screen equals. However, Fox Searchlight wasn’t going to risk splitting the vote, so the studio campaigned Stone and Weisz — who had each already won Oscars — as supporting roles.

The same strategy worked for Mahershala Ali, who won his second supporting actor Oscar for “Green Book” after it was decided that his co-star Viggo Mortenson would compete for lead.

This year, a similar scenario is playing out with DiCaprio and Pitt in Quentin Tarantino’s “Once Upon a Time in Hollywood.” While both share a good deal of screen time, the film’s story really revolves around DiCaprio’s role as fading 1960s Hollywood star Rick Dalton who continues to employ his former stuntman Cliff Booth (Pitt) as a kind of guy Friday who’s become the actor’s driver and handyman.

Sony hasn’t revealed its plans yet but several insiders think the studio will position DiCaprio in lead and Pitt in supporting.

An Academy member tells me: “It’s the best work Brad has ever done but it’s all driving Rick’s narrative.”

Another source I spoke with suggested that Pitt likely sees the writing on the wall. “I can actually see Brad volunteering to be in supporting hoping he’d get it because most people think Leo is the lead,” says the person.

And, fortunately, it doesn’t sound like Pitt’s ego will drive him to push for lead. “He’s one of the most chill guys,” says an executive who has worked with Pitt on both acting and producing projects. “He doesn’t think about the awards stuff. He’s a filmmaker and his priority is making good films.”

Pitt has already earned three Oscar noms — supporting in 1996 for “12 Monkeys,” followed by best actor nods in 2009 for “The Curious Case of Benjamin Button” and “Moneyball” in 2012. Perhaps a fourth time could be the charm.

Hollywood hasn’t always been keen on awarding Oscars to one co-star over another when they’re both nominated in the lead acting category. In the 17 times that co-stars have been nominated in the leading category, five have actually gone on to win.

Studios and awards consultants seem to have learned a lesson because the last time two leads were up against each other was in 1992, when Susan Sarandon and Geena Davis were both nominated for “Thelma & Louise.” They lost to Jodie Foster, who went home with her second Oscar for “Silence of the Lambs.”

Sony isn’t the only studio looking at two actors in leading roles in the same movie for the 2020 Oscars race. Fox has “Ford v Ferrari” to sort out. The title alone pits its two leading men, Matt Damon and Christian Bale, against each other in what one would assume are two leading roles.

And, I’m already hearing that Netflix will back Robert De Niro for lead in Martin Scorsese’s Mafia epic “The Irishman” and Al Pacino and Joe Pesci for supporting.

As for Robert Eggers’ pure two-hander “The Lighthouse,” a source tells me A24 is probably setting Robert Pattinson up for lead and Willem Dafoe for supporting.

Another possible contender is Netflix’s Vatican drama, “The Two Popes.” Jonathan Pryce will likely receive a leading campaign for his work as Pope Francis. Anthony Hopkins will head into awards season with the supporting campaign for his work as Pope Benedict XVI.

While pushing one lead of a two-hander to supporting could cause some awkwardness and tension between the actors, “it’s also an embarrassment of riches,” one studio executive said. “It’s a good problem to have.”

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