Who Will Win? Handicapping the Most Unusual Oscars Ever

After the longest Oscar season in history, the big day is finally upon us. This Sunday, the hostless, socially distanced 93rd Academy Awards will be handed out in a three-hour ceremony broadcast live from both the Dolby Theatre in Hollywood and downtown LA's Union Station.

Most of the major awards feel all sewn up this year, which makes me suspiciously confident in my choices, but a longer Oscar season (the awards were pushed back two months because of COVID) means that voters have had more time to ponder their choices. Some films that peaked in February ("Ma Rainey's Black Bottom," for example) have fizzled a bit; others, like "The Father," have surged in the final days of voting, which could lead to a couple upsets.

This longer timeline – in addition to a more diverse Academy than ever before – could spell trouble for those Oscar prognosticators among us who have learned how to think like an Oscar voter, who. until quite recently were still largely very old, very white, and very male.

Best Picture

This ought to be as close to a slam dunk as it gets. While I wouldn't be mad at a surprise victory for the tender, exquisite "Minari," everything looks to be tilting in "Nomadland's" favor. It was the perfect film for 2020, a year when many felt unmoored and began to consider – albeit in isolation – alternative ways of happiness, living, and community, all the while looking forward to a day "down the road" when we would see our loved ones again.

Should Win and Will Win: "Nomadland"

Actor in a Leading Role

I'd wager that there are very few people alive who don't know that Chadwick Boseman is on track to win this posthumously. While there is no good reason to bet against him now, "Ma Rainey's Black Bottom" peaked early and the film suffers in that it often feels like a televised play. There is chatter that Anthony Hopkins is picking up steam for his career-best performance in "The Father," but Boseman is still the one to beat.

Should Win: Riz Ahmed, "Sound of Metal"
Will Win: Chadwick Boseman, "Ma Rainey's Black Bottom"

Actor in a Supporting Role

Like Boseman, there is one other performance that has won all the precursor awards and seems to have built an insurmountable momentum. Daniel Kaluuya is excellent in "Judas and the Black Messiah" and is the almost certain winner. There could be strong industry support for film veteran Paul Raci, who is the heart of "Sound of Metal," and for Lakeith Stanfield, who landed a surprise nomination in this category despite campaigning as leading actor, which points to an awful lot of support.

Should Win: Lakeith Stanfield, "Judas and the Black Messiah"
Will Win: Daniel Kaluuya, "Judas and the Black Messiah"

Actress in a Leading Role

This category gives me anxiety. Predictions are all over the map on this one, and even as I type this, I oscillate between three of these five women. If Frances McDormand hadn't just won her second Oscar two years ago, she would be a shoo-in for her sensitive turn in "Nomadland." Andra Day is probably a long shot at this point, although I consider her revelatory turn in "The United States vs. Billie Holiday" to be the best of the year, and she did win the Golden Globe. Carey Mulligan won virtually no major precursor awards for "Promising Young Woman," which spells trouble for her, but the Academy tends to favor young, white women in this category, which is something else to keep in mind. Viola Davis became the most nominated black actress with this nomination for "Ma Rainey's Black Bottom," and she is overdue for a second Oscar. But "Ma Rainey" is a flawed film, Davis has under 30 minutes of screen time, and the performance feels a bit slight. This is really the question here: Does McDormand deserve a third Oscar before Davis deserves her second? That conundrum could pave the way for Mulligan to swoop in, which wouldn't be the worst thing in the world. The bottom line is this: Close your eyes and point to a name. It could be anyone.

Should Win: Andra Day, "The United States vs. Billie Holiday"
Will Win: Frances McDormand, "Nomadland"

Actress in a Supporting Role

This category was wide open a few weeks ago, but the tea leaves have recently become a lot clearer. Amanda Seyfried was the frontrunner all year for "Mank," but the film's momentum died, and Olivia Colman might have been in a better position to win for "The Father" if she hadn't just won two years ago. As for Maria Bakalova, ingenious in the "Borat" sequel, the nomination is her prize. The big question is whether the Academy will finally give Glenn Close her long overdue Oscar, despite "Hillbilly Elegy's" awful reviews. Smart money is on Yuh-Jung Youn for "Minari," and her win here would make history as the first Korean actor to win an Oscar, and only the second Asian woman.

Should Win and Will Win: Yuh-Jung Youn, "Minari"

Adapted Screenplay
Should Win and Will Win: "Nomadland"

Original Screenplay
Should Win and Will Win: "Promising Young Woman"

Animated Feature
Should Win and Will Win: "Soul"

Cinematography
Should Win and Will Win: "Nomadland"

Costume Design
Should Win and Will Win: "Ma Rainey's Black Bottom"

Directing
Should Win and Will Win: Chloé Zhao, "Nomadland"

Documentary Feature
Should Win and Will Win: "My Octopus Teacher"

Documentary Short Subject
Should Win and Will Win: "A Concerto is a Conversation"

Film Editing
Should Win and Will Win: "Sound of Metal"

International Feature Film
Should Win: "Quo Vadis, Aida?"
Will Win: "Another Round"