Right now, it seems like it's Pitt's to lose. The Last Major Movie Star has an Oscar for producing 12 Years a Slave, but has never gotten one for acting and the industry seems eager to give him his due. Cliff Booth is sort of the perfect Pitt role as well. The stunt/handyman, who may or may not have killed his wife, oozes a lackadaisical charisma tinged with menace. He's another avatar of masculinity, the kind Pitt has been playing with since his Tyler Durden days. It will only help his case that he's equally as good in Ad Astra, a film which doesn't have quite the same awards traction, but is impressive nonetheless.
The other contenders
Pitt's biggest competition comes from The Irishman camp, where there are strong cases for both Joe Pesci and Al Pacino. Pesci returns for his first on-camera role in nearly a decade playing the sly Russell Bufalino, the mafioso that employs Robert De Niro's Frank Sheeran. Pacino, naturally, has the more showy part, but he harnesses his blustering loudness well as famed union boss Jimmy Hoffa. There's a lot of yelling, but it's good yelling. However, the Oscars are not a meritocracy, and who wins often comes down to who campaigns for the prize. It seems unlikely that Pesci, who has retreated from the public eye in recent years, will do that. Even Pitt has been known to be reticent to play the game. (He skipped the ceremony when Moonlight, which he executive produced, won Best Picture.) Still, the power of Pitt might be impenetrable.
The last three spots seem up in the air. The Academy, bizarrely, has been cool on Tom Hanks, ignoring his impressive work in, say, Captain Phillips. The temperature may soon turn, thanks to his performance as Fred Rogers in A Beautiful Day in the Neighborhood, which is, yes, very much a supporting role. (Matthew Rhys' journalist is the lead.) I'm going to wager the last spot goes to Anthony Hopkins, who is surprisingly funny as Pope Benedict XVI, one of the two popes in The Two Popes. Jamie Foxx as a death row inmate in Just Mercy could land in the category as well.