It’s supposed to be easy this year: La La Land dances away with Oscar’s gold. That’s what most of the pundits, oddsmakers and advance kudos say.

Damien Chazelle’s romantic ode to Hollywood movies and musicals is indeed the film to beat at Sunday’s 89th Academy Awards, with a record-tying 14 nominations to its name. The last two films to have 14 noms, Titanic (1997) and All About Eve (1950), both took Best Picture along with numerous other Oscars.

But these two movies triumphed in years when a simple majority of votes could win Best Picture. The preferential ballot now employed for this category means that second, third and subsequent choices also factor in. This means challengers like Moonlight and Arrival, with eight nominations apiece, could snatch the top gold away from La La Land.

And we can’t rule out a come-from-behind win by the crowd-pleasing Hidden Figures, currently the domestic box-officer leader among the nine Best Picture nominees, which also include Manchester by the Sea, Hacksaw Ridge, Lion, Fences and Hell or High Water.

There are also potential upsets in store for other categories. Here’s my annual will/could/should predictions for Oscar night:

Best Picture

Will:La La Land or Moonlight

Could:Hidden Figures

Should:Moonlight

Why: The safe money is supposedly on La La Land to win, but I consider this category too close to call. Moonlight’s unique coming-of-age story has so much resonance to modern times, I’m thinking — hoping — that the Academy will go for it. And Hidden Figures just might surprise everybody, much like Spotlight did last year.

Best Director

Will: Barry Jenkins, Moonlight, orDamien Chazelle, La La Land

Could: Denis Villeneuve, Arrival

Should: Barry Jenkins

Why: Best Director and Best Picture were historically awarded in lockstep, but recent times have changed that unofficial tradition. If voters go La La Land for Best Picture, then I think they’ll choose Jenkins for Best Director, which would significantly make him the first African-American director to win this honour. And if they choose Moonlight for Best Picture, then Chazelle for Best Director. Of course, they might go in an entirely different direction and choose Canada’s Villeneuve, for his sci-fi wonder Arrival.

Best Actress

Will: Emma Stone, La La Land

Could: Natalie Portman, Jackie or Isabelle Huppert, Elle

Should: Natalie Portman, Jackie

Why: Front-runnerStone is all set to be the belle of the Oscars with her enchanting performance playing an aspiring Hollywood actress. But the inner fortitude Portman displayed as the widowed Jacqueline Kennedy impressed me more. Huppert is long overdue for an Oscar and a win is both possible and deserved.There’s a wealth of riches in this category: Ruth Negga (Loving) and Meryl Streep (Florence Foster Jenkins) would also be worthy winners.

Best Actor

Will: Casey Affleck, Manchester by the Sea

Could: Denzel Washington, Fences

Should: Casey Affleck, Manchester by the Sea

Why: Affleck and Washington each play tortured souls in their respective roles of defeated family men. Affleck’s performance was bone deep and truly memorable; Washington’s was solid yet showy. But Denzel is a two-time Oscar champ and he won at SAG this year, so this may be a Casey at the Bat story — and you know what happened to that other Casey.

Best Supporting Actress

Will: Viola Davis, Fences

Could: Michelle Williams, Manchester by the Sea

Should: Naomie Harris, Moonlight

Why: This is the easiest Oscar to call and the toughest to endorse. Davis will win for her tremendous performance as the stoic wife in Fences, although it’s arguably category fraud: she really should be up for Best Actress.

Williams defines strong support with her brief Manchester scenes, including one showstopper that breaks all hearts. But Harris exceeds all stereotypes and invites empathy with her moving portrayal of a junkie mom in Moonlight.

Best Supporting Actor

Will: Mahershala Ali, Moonlight

Could: Jeff Bridges, Hell or High Water

Should: Mahershala Ali

Why: Ali has been the obvious choice here ever since he first Sekabet wowed audiences at TIFF and other fall festivals with his deeply affecting and stereotype-busting portrayal of a fatherly drug dealer in Moonlight. It will be a huge upset if he loses — but if he does, the prize would likely go to Jeff Bridges for his wily lawman character of Hell or High Water.

Best Original Screenplay

Will: Manchester by the Sea

Could: La La Land

Should: Manchester by the Sea

Why: Voters often bestow this as a consolation prize to films they aren’t choosing for Best Picture, so Manchesterby the Sea may win for that reason. More than this, though, writer/director Kenneth Lonergan truly deserves recognition for finding a beating heart within the depths of tragedy and despair, and also some welcome notes of comedy. La La Land wins here only if voters are completely besotted by the film, which they may be.

Best Adapted Screenplay

Will: Moonlight

Could: Arrival

Should: Moonlight

Why: How do you find poetry in a crime-infested and crack-ridden Miami neighbourhood? Writer/director Barry Jenkins shows how with Moonlight, only his second film, which he adapted from an unproduced play by Tarell Alvin McCraney. Moonlight is heavily favoured to win, but it would be no shame if Eric Heisserer’s dramatic and impactful adaption of Ted Chiang’s cerebral short story for Story of Your Life took the prize for Arrival.

And the rest …

  • Whether or not it wins the top prize, La La Land will likely be the overall winner Sunday. Those 14 nominations have to count for something, don’t they? Besides possible wins for picture, director, actress and original screenplay, I see it taking gold for cinematography, editing, sound mixing, production design, score and original song (“City of Stars”).
  • Best Animated Feature to Zootopia, the wildly popular story of a world where the animals are running the show. (Insert Donald Trump joke here.) Speaking of animals, Best Visual Effects has to go to The Jungle Book for making believable and fearsome critters out of thin air and digital code.
  • Jackie was robbed of a Best Picture nomination, in my opinion, but it should at least win for Best Costume Design, especially for the perfection of that memory-laden pink Chanel dress worn by Portman. On the other hand, it’s up against the formidable La La Land and the flashy Allied, Fantastic Beasts and Where to Find Them and Florence Foster Jenkins. And for the related category of Best Makeup and Hairstyling, I think the cosmic creations for Star Trek Beyond will boldly go for the gold.
  • Best Foreign Language Film looked like Maren Ade’s to lose, for her hilarious and heartfelt German father-daughter comedy Toni Erdmann. I’m still calling for a win, but Trump’s anti-Muslim travel ban may swing protest votes to Asghar Farhadi’s Iranian drama The Salesman. And we can’t rule out the feel-good vote going for the lovable curmudgeon of Hannes Holm’s Swedish dramedy A Man Called Ove.
  • In my mind there’s no contest for the Best Animated Short winner: Pearl, a father-daughter musical road trip that brought tears to my eyes and also happens to be the first VR film nominated for an Oscar. But the favourite looks to be Disney/Pixar’s Piper, a sweet story of a mother and baby sandpiper vs. scary waves.
  • Best Live Action Short is another tough call — they’re all good — but my favourite is La Femme et le TGV, an enchanting story in the Wes Anderson vein starring the rarely seen Jane Birkin as a lonely baker who finds love both rapid and elusive.
  • We could argue whether or not the nearly eight-hour O.J.: Made in America really qualifies as a film, but its excellence seals the deal as Best Documentary Feature winner — and that’s in a category that includes the first-rate I Am Not Your Negro (opening Friday in Toronto) and 13th. As for Best Documentary Short, Joe’s Violin plucks the right strings with its story of shared musical interests between a 91-year-old Holocaust survivor and a 12-year-old Bronx schoolgirl.
  • Finally, if La La Land wins Best Sound Mixing as I predicted above, then Hacksaw Ridge will likely beat it for Best Sound Editing. Why? Because the Academy often chooses musicals for Best Sound Mixing but it loves noisier movies for Best Sound Editing. Hence war film Hacksaw Ridge, likely the only Oscar for Mel Gibson’s comeback movie. Which seems about right — La La Land can’t win everything, can it?

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