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2027 Oscar Predictions: Can Matt Damon Finally Win a Best Actor Oscar for The Odyssey?

Sasha Stone by Sasha Stone
July 17, 2026
in BEST PICTURE, featured
152
2027 Oscar Predictions: Can Matt Damon Finally Win a Best Actor Oscar for The Odyssey?

The Odyssey has finally opened. The reviews are stellar. The box office prospects look good. Now, all that’s left is to figure out how many Oscars the film will win. I expect, having now seen the film, that the so-called “woke” controversy will do a lot of the heavy lifting here. We’re talking teary-eyed standing ovations, major applause, lots of covers on magazines for Lupita Nyong’o and so it will go. It will be one virtue signal after another as the Good People of the Left double down on their righteous fury against the MAGA Right.

As for the film itself, I generally do not write reviews of films I don’t love so I won’t be writing a review of this movie. I found it to be as opaque and inaccessible as the Dune films. That doesn’t make it bad necessarily but I am now wondering how it will play with Oscar voters. The “new” Oscar voters are hard to predict. I can say with certainty that there is a good chance the Old Oscar Voters would not have chosen it because it is a confusing sit and the characters don’t offer much in the way of emotional depth.

I won’t go into it too much, because probably you’ve dragged yourself here from Twitter to call me a “racist” or else you’re here for Oscar talk. I will be posting something more in-depth over at my other movie site, Hollywood Woketopia, if you are interested, although there I will be writing more on the culture war than the movie itself.

The story of The Odyssey is fairly straightforward. It is easy to follow and has laid the groundwork for so many films and stories that came after. However, in Christopher Nolan’s hands, it’s been chopped up and deconstructed to, in my view, depict not so much a time and place as an idealized view of a utopian society as imagined, or reimagined, by today’s progressive Left. I would call it Peak Woke.

By that, I mean, what we see on screen is not a place that exists in real life. It is similar to the idealized Americana of the 1950s where we saw a lot of nuclear families that seemed to project “normal” life. We also saw a lot of sword and sandal or religious epics. The idea was to firm up the American ideal of patriotism against the existential threat of Communism.

Civil Rights was not yet a threat, that would come later, as would women’s rights and gay rights but the 1950s had the top neatly placed on top of the apple pie and pinned down. That’s very much like today’s Left as politics and culture have merged in the same way it did in the 1950s. The existential threat now would be Donald Trump, “toxic masculinity,” the “white male patriarchy,” and especially, the idea that there are racists and transphobes and bigots and homophobes everywhere.

So, instead of blacklists, we have cancel culture. Because Trump won again, we don’t really have the kind of tribunals we had then. Even with the DEI panels and the fury over stupid Jimmy Kimmel jokes, the Left still maintains the cultural power so nothing will happen to any of them, not in the same way Communists or sympathizers were punished in the 1950s.

Yes, the same people who did not reward Sinners last year love to call everyone who doesn’t agree with them or speak and think the way they do, “racists.” They also have no problem with how activists force white actors out of parts in films but also have a fit if anyone dares to complain about casting the other way. It’s just the hypocrisy we’re all meant to understand now that the hierarchy’s reversed.

At any rate, The Odyssey is Peak Woke, like One Battle After Another, Wicked, and other films that depict the worldview of today’s Left, as opposed to, say, Project Hail Mary, Obsession, Backrooms, or other films that exist outside of the partisan divide. One Battle saw racism and ICE as the existential threats humanity faced; the threat in The Odyssey is not far off. It is still about an end-of-the-world vibe, a failed humanity at the hands of men, an attempt to redeem the female characters, etc.

The biggest flaw in the film, in my view, and it is in keeping with Peak Woke movies, is the stripping of any kind of sexuality, especially with Circe (Samantha Morton) and Calypso (Charlize Theron). These women were having sex with Odysseus, but there is none of it in the film. It’s far too glum and serious for that. Odysseus himself is also stripped of his own sexuality and any temptation therein. These are morally pure characters, and sex would muddy the water in that regard. But let’s just say, it’s greatly missed.

There are no sharply drawn supporting characters, and I don’t think any of them have enough screen time for a supporting nod, certainly not Lupita Nyong’o, who was cast only to sit there and symbolize Helen of Troy from this feminized perspective. She isn’t depicted as the ideal male object of desire so much as someone who is a tool to be used and disposed of by powerful men.

The rest of the characters are one-dimensional, and I don’t know how many of them will stand out for an Oscar nod. It’s probably safe to go with Anne Hathaway, though Samantha Morton is good. Elliot Page could also squeeze in for a history-making nod.

Where the Odyssey will do really well is with the crafts, no doubt about it. It’s probably walking in the door winning Visual Effects, Costumes, Makeup, and Hair, maybe? Casting probably. And I don’t know how far it will go beyond that. It is probably the frontrunner at this moment, but I still think Project Hail Mary is the better film, even if movies with small casts like that don’t really win Best Picture, and it’s a movie that most definitely is not Peak Woke, and thus, will there be any urgency to vote for it?

Voting for The Odyssey gives the virtuous something to get behind, a way to stick it to the Right, like they did last year. That’s certainly possible, but I kind of think that for a movie to win Best Picture, people have to at least understand it, and I’m not sure that everyone will get this movie.

But The Odyssey winning Best Picture is good for Hollywood because blockbusters like this should be rewarded for reaching a broad audience. Whether it will win or not, I do not know.

That said, Matt Damon is as good as he has ever been and might give a career performance here. I can see him winning Best Actor for this. He has more than paid his dues in Hollywood, always turning in great performances and is one of the nicer actors I’ve ever met doing this job, I would have to admit. He is very well liked in Hollywood and is an adjunct, it goes without saying, with Ben Affleck, George Clooney, etc.

I think my favorite performance of his is still The Talented Mr. Ripley. But you know, he’s always good in everything he does. He’s never been put through as much as he has in The Odyssey. It is a career best.

That puts him squarely up against Tom Cruise in Digger, who is playing the kind of villain in keeping with Peak Woke, and thus, there could be some urgency to vote for him.

So Best Actor/Best Picture could line up like this:

Matt Damon — The Odyssey
Ryan Gosling — Project
Tom Cruise — Digger
John Malkovich — Wild Horse Nine
Brad Pitt — The Adventures of Cliff Booth
Sebastien Stan, Fjord

But given The Odyssey’s heft and social importance, I’d probably hand the win to Damon, as he’ll be a character people will root for. On the other hand, nice guy Tom Cruise could also finally be in line for an Oscar. At this moment, it’s probably between these two.

Three of these films haven’t been seen yet, and it’s always a gamble to go that way. If I showed you my predictions from last year at this time, you would laugh. There is almost no point in predicting things, but it’s just a trap we all fall into because there is nothing else to do.

I don’t have much more to add – go see the movie and let us know what you think.

Best Picture
The Odyssey
Project Hail Mary
The Adventures of Cliff Booth
Fjord
La Bola Negra
Wild Horse Nine
Dune III
Digger
The Debut
Obsession

Director
Christopher Nolan, The Odyssey
Christian Mungiu, Fjord
Javiers, La Bola Negra
David Fincher, Adventures of Cliff Booth
Martin McDonagh, Wild Horse Nine

Actor
Matt Damon, The Odyssey
Tom Cruise, Digger
Sebastien Stan, Fjord
Ryan Gosling, Project Hail Mary
John Malkovich, Wild Horse Nine

Actress
Julianne Moore, The Debut
Renate Reinsve, Fjord
Michelle Williams, A Place in Hell
Sandra Huller, Fatherland
Ruth Madeley, Being Heumann

Supporting Actor
Paul Giamatti, The Debut
Sam Rockwell, Wild Horse Nine
Jeremy Strong, The Social Reckoning
Edward Norton, The Invite
Guitarricadelafuente, La Bola Negra

Supporting Actress
Lupita Nyong’o, The Odyssey
Sandra Huller, Project Hail Mary
Anne Hathaway, The Odyssey
Penelope Cruz, La Bola Negra
Parker Posey, Wild Horse Nine

Original Screenplay
Fjord
Wild Horse Nine
Digger
The Debut
Behemoth!

Adapted Screenplay
The Odyssey
Project Hail Mary
La Bola Negra
The Invite
The Adventures of Cliff Booth

Casting
The Odyssey
The Debut
Being Heumann
Behemoth!
The Invite

Visual Effects
The Odyssey
Project Hail Mary
Dune: Part Three
Werwulf
Disclosure Day

Cinematography
The Odyssey
Project Hail Mary
Dune: Part Three
Werwulf
The Adventures of Cliff Booth

Tags: 2027 Oscar PredictionsThe Odyssey
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