And just like that, Sean Penn became the eighth actor to win three Oscars.
With One Battle After Another, Sean Penn became the eighth person in Academy Award history to win a third acting Oscar. He follows Supporting Actor king Walter Brennan, most honored thespian ever Katharine Hepburn, Swedish superstar Ingrid Bergman, New Hollywood enfant terrible Jack Nicholson, nomination queen Meryl Streep, method actor extraordinaire Daniel Day-Lewis, and too-cool-for-school Oscar favorite Frances McDormand. This honor comes after a period when Penn was fairly removed from the awards conversation, regularly panned at Cannes for his directorial work while winning the favor of a few critics for underseen performances like those in Daddio and Asphalt City. Indeed, he seems so uninterested in playing the game that he barely campaigned and didn’t even show up to collect his prize.
Disregarding whether he deserves it or not, Penn’s victory leads me to wonder who’s next? Who is closest to joining this exclusive club? There are currently 19 two-time acting Oscar winners alive, each a different case, with some landing in the “just a matter of time” field, while others are surely “not happening.” Join me as I go over these possibilities…
Sir Michael Caine was last nominated for THE QUIET AMERICAN, in 2002.
NOT HAPPENING
- Michael Caine
- Kevin Spacey
At 93 years old, I doubt Caine will go back to work in a substantial way, no matter how much Christopher Nolan might beg him to consider. Sure, he’s been known to pull a Miyazaki on the public, first announcing his retirement in 2009, then again in 2021 and 2023. Presently, he’s set to narrate a short film by Bella Webber and play a bit part in The Last Witch Hunter sequel. These are hardly the types of projects that earn one Oscar gold. Also, for what it’s worth, no actor has ever been nominated in their 90s, much less won.
As for Kevin Spacey, I don’t think I need to explain why he’s not happening.
At 83, Anthony Hopkins became the oldest person to win the Best Actor Oscar.
UNLIKELY... RIGHT?
- Anthony Hopkins
- Christoph Waltz
Hopkins is also a bit too long in the tooth for AMPAS’ usual way of doing things. However, he’s half a decade younger than Caine and works much more regularly, with seven upcoming projects confirmed already. These include a film about Charles Darwin’s family in the aftermath of his death, in which Hopkins will play the famed naturalist. Then, there’s a Richard Eyre period piece, a Maserati biopic, a Guy Ritchie romp based on a true story, an H.G. Wells adaptation, and so on. Some of these could get into the awards conversation, though Hopkins’ record as a constant featured player in the “This Had Oscar Buzz” podcast would indicate otherwise. The issue is that his second win is very recent, somewhat controversial in some circles, and, moreover, Hopkins won’t be campaigning. Unless he’s “undeniable,” it’s very unlikely. Plus, though I love him, the man can be guilty of going through the motions on autopilot.
Waltz’s situation is somewhat distinct. He still has many years ahead of him, and mainstream auteurs with access to big Hollywood budgets seem to love to feature him in colorful supporting roles, so he’s sure to get back into the conversation sometime in the future. And yet, his range is very limited, with the actor doing little to challenge himself when picking projects. Is anyone passionate about giving him a third Oscar when his second win hasn’t aged very well already? I guess a similar thing could be said of Penn, and he still did it. Am I letting the fact that I like Sean Penn much more as an actor influence my thought process here? Maybe. In any case, if Stephen Frears’ Billy Wilder drama ever gets made and earns good reviews (I have doubts), we’ll have to rethink these things.
At 29, Adrien Brody became the youngest Best Actor winner ever, for THE PIANIST.
POSSIBLE, BUT I DON’T SEE IT
- Adrien Brody
- Renée Zellweger
- Hilary Swank
Brody, Zellweger and Swank have very weird Oscar histories. Starting with the earliest one to achieve her two Oscars, Swank really fell off, awards-wise, after Million Dollar Baby. And it’s not like voters haven’t had opportunities to throw her a bone either. Remember Conviction? Remember The Homesman? Her recent filmography being so streamer-forward doesn’t make me optimistic either.
Brody has been similarly excluded from the awards season for most of his career, only popping up as a serious contender the two times he won. And it’s not like he hasn’t been in buzzy or even acclaimed work, merely that, as a performer, Brody tends to be recognized as part of ensembles rather than an individual stand-out. That, plus his insufferable speech when winning, may dim his light within the industry. More nominations seem possible, wins unlikely.
Finally, there was a time when Zellweger seemed like she was going to be a perennial nominee. But then she won for Cold Mountain and mostly disappeared from prestige fare, with the occasional Miss Potter as the exception that proves the rule. Maybe the biggest cause of my skepticism is that, instead of capitalizing on her second win, Zellweger was content to do her own thing, not chase further prestige. Which is a pity because, truth be told, she’s at the top of her game in stuff like the latest Bridget Jones movie. Seriously, she’s better in Mad About the Boy than in both her Oscar-winning turns.
If not for Anne Hathaway, Sally Field might have won a third Oscar for LINCOLN.
POSSIBLE, WITH THE RIGHT PROJECT
- Mahershala Ali
- Sally Field
- Jane Fonda
- Dustin Hoffman
- Jessica Lange
- Dianne Wiest
All of these people need the right vehicle to bring them back into the fold. As the youngest of the lot, Ali is the likeliest to return as there will be plenty of opportunities, though perhaps he’ll have to wait a while before an “elder statesman” sort of narrative can propel him to victory.
The remaining thespians could conceivably happen at any moment, if they were only given the chance. Since Hollywood rarely extends such gifts to women of a certain age, Field, Fonda, Lange, and Wiest will struggle more than Hoffman. On the other hand, someone like Fonda seems much more beloved within the industry, still very much in the public eye and unafraid to ruffle feathers. Can you imagine her in a full-throttle Oscar campaign, right now? In Lange’s case, there’s some bitterness to this speculation because she did get the right project. Well, the right role. And yet, her turn as Mary Tyrone in Jonathan Kent’s adaptation of Long Day’s Journey Into Night seems fated to never see the light of day. It’s played some festivals to middling notices, yet distributors still seem uninterested.
Back then, who could have guessed BIRDMAN would be the start of such a successful Oscar run for Emma Stone?
PROBABLE, BUT IT’LL TAKE A WHILE
- Emma Stone
AMPAS is obsessed with Stone in a way that reminds me of Streep and Lange in the 80s. In other words, as long as this industry’s affection lasts and the roles keep coming, she’ll stay in the Oscar bubble. Will she win another one soon? That’s another story altogether. Stone is just 37, nine years younger than the youngest person to get to three, and Walter Brennan’s road to his record is pretty shifty and impossible to replicate by today’s stars. Daniel Day-Lewis is next, at 55, a milestone that’s still a decade away for Stone. Of course, the Academy doesn’t obey precedent or mathematical nonsense like this by any intention, yet such numbers reveal they like to wait until a thespian is a certain age before elevating them to this level. At the end of the day, it might just be a matter of a third feeling too soon, lacking in urgency, with the thought prevailing that she’ll still have countless opportunities to accomplish it ahead of her.
29 years after NELL, Jodie Foster finally received her fifth Oscar nomination for NYAD.
QUITE LIKELY
- Jodie Foster
- Tom Hanks
For a long time, it felt like Foster and Hanks were cursed never to be nominated again after their hot streaks faded away. Nevertheless, they’ve both jumped back into the Oscar race this last decade, with Nyad and A Beautiful Day in the Neighborhood, respectively. With their status as some of our last movie stars, their widespread popularity within the industry and the general public, and a new commitment to interesting projects and roles, a return to the Oscar stage could be in their immediate future. For Hanks, this might happen sooner rather than later, as he’s starring in Lincoln in the Bardo, a George Saunders adaptation to be directed by Duke Johnson that’ll see the two-time Oscar winner play the 16th President facing the loss of his son, caught in the space between life and death.
With BLUE JASMINE, Cate Blanchett had one of the biggest awards season sweeps in history.
JUST A MATTER OF TIME
- Cate Blanchett
It almost happened with Tár and, depending on who you ask, it SHOULD have happened. Right now, it feels like just a matter of time before Cate Blanchett is back on TV with a little golden guy in her grasp. From her upcoming projects, Alice Birch’s Sweetstick appears to be the most promising. Official materials describe the story thus: “A mercurial woman with a strange and piercing gift - the ability to see what others most intimately need, often at great personal cost - sets out on a journey home.”
Blanchett as a three-time Academy Award winner just feels correct in a manner that’s hard to articulate. I’m not even one who’d advocate for her deserving of this triple honor, but she fits right into the group of three-peat champions.
Still, not as much as…
It has been 25 years since Denzel Washington won Best Actor for TRAINING DAY.
OVERDUE, ACTUALLY!
- Robert De Niro
- Denzel Washington
Don’t these two feel like they should already be three-time winners? De Niro hasn’t won since 1980’s Raging Bull, though he’s bested himself various times since then. I’m thinking of his unnominated turns in The King of Comedy and The Irishman, plus his Oscar-heralded work in Cape Fear and Killers of the Flower Moon. Even when one steps outside Martin Scorsese’s filmography, there’s much to consider in De Niro’s post-Raging Bull repertoire, including stellar work with Leone, Mann, Tarantino, and so forth. Hell, he would’ve already felt like a deserving three-time winner by the time his Jake LaMotta came around, since he was nominated in ’76 for Taxi Driver and ’78 for The Deer Hunter. He just needs a juicy enough role and the right season to score gold. Maybe Dito Montiel’s After Exile could do the trick?
Washington is in a similar boat in that, according to several people, he should already be a three-time Oscar winner. Looking at my own ranking of nominees, he’d have gotten my vote for Best Actor in 1992 for Malcolm X and 2016 for Fences. But that’s behind us, so let’s focus on the future. Right now, he’s got a Fernando Meirelles crime drama coming up, along with a Hannibal biopic with Antoine Fuqua at the helm. If neither of those works out for him regarding Oscar, there will still be many opportunities to come, as Washington is regarded by his peers and other filmmakers as something of a living legend. Some could argue his relative unwillingness to play the campaign trail or do full-throttle promo tours could hurt him, but that didn’t hinder Penn, so it shouldn’t hinder Washington.
Who do you think is next to three acting Oscars? And, if you had to choose, which of these thespians would you have already given a third Academy Award to?