The Ankler

Pitt, Cruise, Pattinson, Damon: The Most A-List Best Actor Race Ever

What do Oscar voters really want from a movie star? We’re about to find out

Even after all the heartening box office news we’ve had this year, I’m not sure anyone expected a banner moviegoing weekend in September — much less one in which two unusual star vehicles out-grossed the new family animated offering (Forgotten Island) but not Marvel’s Avengers: Endgame re-release.

Brad Pitt’s survival thriller Heart of the Beast probably won’t be mentioned again in this awards season-obsessed newsletter, but it does seem like a good omen for his upcoming Netflix film The Further Mis-Adventures of Cliff Booth; and Primetime has become the year’s third success in a row for Robert Pattinson, who has bolstered his best actor buzz with a solid $19 million opening weekend. 

Pitt for Booth and Pattinson for Primetime are set to be part of yet another especially starry best actor race, which may be even more competitive than last year’s thrilling contest — and it’s got me thinking about how major stars navigate the modern Oscars, a much trickier proposition than it used to be. 

Of course the Oscars love movie stars, but usually not for the reasons audiences do. Major stars who have won best actor have usually done it through physical transformations (Gary Oldman in Darkest Hour, Brendan Fraser in The Whale, Matthew McConaughey in Dallas Buyers Club), grueling physical challenges (Leonardo DiCaprio eating bison liver in The Revenant, Eddie Redmayne confining himself to a wheelchair for The Theory of Everything), or simply doing something different from what made them beloved stars in the first place (Will Smith in King Richard, Tom Hanks in Philadelphia). 

All of those paths to victory are plausible in this year’s race, which features a high number of top names from the past century as well as newer arrivals still cementing their place in the A-list. I’m sure we’ll hear plenty in the coming months about hours spent in the makeup chair applying prosthetics, about vocal, movement and dialect coaches and all the external work that so often gets equated with Oscar-worthy acting. But I’m also here to celebrate the movie stars onscreen this year just doing what they actually do best: being undeniably magnetic.

Today I’m breaking down how stars are fitting into this year’s Oscar race, the historical precedent they’re trying to follow and the challenges that might await them in what’s already a very, very crowded field. I’m using my own fuzzy definition of movie star for this — think the top of the A-list, like Pitt and Pattinson — so, don’t worry, there will be plenty of time to talk about Andrew Scott, Andrew Garfield, Pedro Pascal, John Malkovich, John Turturro and many more.


1. Damon: Leader of an Epic

The movie: The Odyssey

Age: 55

The Oscar history: Three acting nominations; one win for screenwriting

The narrative: The last time Matt Damon was nominated for an acting Oscar, for The Martian in 2015, he lost to a fellow A-lister giving a physically demanding performance in a large-scale epic that was a best picture frontrunner — DiCaprio in The Revenant. This time it’s Damon in the driver’s seat, with Ryan Gosling the one solving problems in space in a movie based on Andy Weir’s work (more on Gosling in a moment). 

DiCaprio’s win for The Revenant was driven more than anything by the sense that he was overdue for his first Oscar, which is not exactly Damon’s situation; he and Ben Affleck famously won writing Oscars together for Good Will Hunting in 1998, but I don’t think I’m the only one who’d argue that a star of Damon’s generational stature ought to have an acting trophy, too. His performance in The Odyssey has pretty much everything you could ask for, from dramatic weight loss to combat training to a big emotional moment both devastating and memeable. 

Best of all, to me, The Odyssey uses Damon’s star persona perfectly as the friendly dad you’d actually follow into battle and back again. For most of the film, Damon’s Odysseus is a noble leader doing the best he can, which makes the guilt-ridden turn at the end so incredibly effective. Damon has played with that inherent likability in fascinating ways throughout his career, from the killer in The Talented Mr. Ripley to the compulsive liar in The Informant! to the crazed astronaut in Christopher Nolan’s Interstellar. But The Odyssey is the best use I’ve seen of everything Damon can do: a striving leader as flawed as the rest of us. 

What history can tell us: This one is pretty obvious — Cillian Murphy won best actor for the titular role in Nolan’s Oppenheimer just two years ago. Other stars of epic best picture winners who have also taken home best actor include Russell Crowe (Gladiator, 2000), Ben Kingsley (Gandhi, 1982) and Marlon Brando (The Godfather, 1972). There’s a historical warning in there too, though: Peter O’Toole earned his first of eight Oscar nominations for Lawrence of Arabia, a best picture winner that took home zero acting awards. Sometimes in an epic film, it’s too easy to let the actors get lost in the shuffle. 


2. Gosling: Army of One

The movie: Project Hail Mary

Age: 45

The Oscar history: Three acting nominations, zero wins

The narrative: So if Matt Damon is the Leonardo DiCaprio of this year, Ryan Gosling is undeniably the Matt Damon. (How’s that for a math equation?) Project Hail Mary is an easy awards-season comparison to The Martian, the last adaptation of an Andy Weir book about a lone man of science trapped in space. The Martian earned seven Oscar nominations, including one for Damon; Project Hail Mary is positioned for even more — it has a head start with its spring release (voters already know they liked it!) and a massive box office haul that shows its cultural staying power.

Gosling is at a similar point in his movie-star trajectory to where Damon was with The Martian. A reliable screen presence for more than 20 years, Gosling has led a wide range of risky indies and, more recently, celebrated blockbusters, with the halo effect of Barbie very much contributing to Project Hail Mary’s success. Making La La Land seems to have permanently unlocked Gosling’s lighter side, and Project Hail Mary takes full advantage of his comic timing as well as his dramatic chops. Yes, Damon’s performance in The Martian shares a lot of the same DNA, but it’s hard to imagine anyone other than Gosling trading quips with a puppet alien and making it feel fully believable. 

What history can tell us: Well, Damon lost for The Martian, so that’s not great. But Gosling feels like this year’s closest equivalent to Michael B. Jordan in Sinners, a well-liked star leading a springtime hit with a performance that looks deceptively simple but carries much of the film on those well-muscled shoulders.


3. Cruise: The Big Swing

The movie: Digger

Age: 64

The Oscar history: Three acting nominations; an honorary Oscar last year.

The narrative: It is still a little funny to me that after months of hiding Tom Cruise’s face in the early marketing for Digger, those extensive prosthetics more or less just make him look… exactly his age. Still, early responses to Digger suggest Cruise is really going for it, with a performance far from the Ethan Hunt/Maverick hero persona he’s kept onscreen for more than 15 years. (I’m sure some people think there are major differences between his Jack Reacher and Mission: Impossible performances, but they are not convincing me!)

Those early responses to Digger are also, as you’ve surely heard, mixed to say the least — and the box office prospects for this weekend aren’t looking so strong either. Digger probably won’t be a star-led hit like The Odyssey or Project Hail Mary, but Cruise still feels very competitive for a nomination, which would be his first for acting since Magnolia 26 years ago — both because of his still-significant star power and his well-documented ability to work a room during awards season. 

What history can tell us: Many, many actors have been praised for becoming “unrecognizable” on their way to winning statues, but having that kind of success when the movie around you isn’t a slam dunk is a bit trickier. Reviews for The Whale were tepid at best and box office was so-so, but Brendan Fraser — with all due respect, a much less significant star than Cruise — swept toward that best actor win. Forest Whitaker’s performance in The Last King of Scotland was much more popular than the movie itself, and he’s actually the last best actor winner to be the sole nominee for his film, a record Cruise may very well wind up repeating. Honestly, we’ll have to wait for Digger’s opening-weekend receipts to agree on exactly what its historical comparison might be.


4. Pattinson: The Moment

The movie: Primetime

Age: 40

The Oscar history: Never nominated

The narrative: Though he’s been making auteur-driven, boundary-pushing indies consistently since even before he was done with his Twilight duties, Pattinson has never really been in the mix for an Oscar until this year — and, boy, has he given us a lot to choose from. He stole every scene as the sniveling villain in The Odyssey and is now in theaters as a different kind of menace, playing Chris Hansen in Primetime. All of this after kicking off the spring box office with the darkly funny The Drama, and all before he’s back in villain mode for Dune: Part Three in December. 

It’s still unclear what Pattinson’s strongest path for a nomination might be, and easy to imagine him being nominated for both Primetime as a lead actor and The Odyssey as supporting; if that happens, he’ll be the first actor nominated in both lead and supporting in the same year since Scarlett Johansson in 2019. He’s undeniably terrific in Primetime, a queasy up-close look at To Catch a Predator in its mid-aughts heyday, with Pattinson playing Hansen as a guy so stuck in his TV host persona he answers a call from his wife with “Hello, this is Chris Hansen.” Pattinson’s interpretation of the real Hansen (who is understandably not thrilled about Primetime) is a worthy addition to the long list of creeps he’s played. But you could also argue that Pattinson isn’t the film’s actual star and that the movie instead belongs to Skyler Gisondo.

The 30-year-old plays one of To Catch a Predator’s “decoys” — actors who can pass for teenagers and lure would-be perpetrators into Hansen’s orbit — and his character is the closest to being the film’s moral center. The response to Gisondo’s performance as an aspiring actor who just wants his SAG card but finds himself ruining lives and falling under Hansen’s spell has been so effusive that I find myself wondering if he’s actually the film’s best shot at an acting nomination. Of course, if that materializes, Gisondo might find himself in a supporting actor field that also includes… Robert Pattinson for The Odyssey.  

What history can tell us: Breaking through with your first Oscar nomination for playing a real person is another time-honored tradition: Rami Malek in Bohemian Rhapsody in 2018, Redmayne with The Theory of Everything in 2014, McConaughey with Dallas Buyers Club in 2013, and that’s just the recent winners. Playing a real person who is also the bad guy is a slightly trickier but no less popular feat, especially when, like Pattinson, you’ve established a reputation for playing bad guys people love to watch.


5. Pitt: An Unlikely Encore

The movie: The Further Mis-Adventures of Cliff Booth

Age: 62

The Oscar history: Four acting nominations, one acting win.

The narrative: Pitt finally won his first acting Oscar in 2019 for playing hard-living stuntman Cliff Booth in Once Upon a Time in Hollywood — and now he’s at it again in The Mis-Adventures of Cliff Booth, a quasi-sequel coming from Netflix in November. The film is already an odd duck, with original director Quentin Tarantino only writing the script this time, and longtime Pitt collaborator David Fincher directing. And it’s very unusual for someone to reprise a role that won them an Oscar, with Joaquin Phoenix’s return engagement as Joker in Folie à Deux probably a solid warning against anyone else trying it.

So will Cliff Booth live up to the Oscar-winning or creative success of its predecessor? It’s anybody’s guess, since as of a few weeks ago people within Netflix hadn’t even seen the film, and reshoots were happening in Los Angeles as recently as August. If Cliff Booth has the goods, it’s very likely the Academy will take notice; the Pitt-led F1 was a surprise best picture nominee just last year, and though Fincher has been out of Oscar’s orbit for a while, he’s a previous best director nominee whom many are eager to welcome back.

What history can tell us: As mentioned, Phoenix’s failure to launch a second time is a big flashing warning sign — though I think there are many reasons to have more faith in Fincher than in Joker director Todd Phillips. Cate Blanchett got nominated for her second go-round playing Queen Elizabeth I in Elizabeth: The Golden Age, though reviews for that 2007 sequel were also less than kind. The best comparison may be Al Pacino’s two nominations for playing Michael Corleone in The Godfather films, an unenviably high bar for Cliff Booth to clear. Still, if anyone is up for that challenge, maybe it’s this team?

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