Who’s our next three-peat champion?
Friday, March 20, 2026 at 5:00PM 
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?
Reader Comments (22)
It’s Blanchett. She could’ve even beaten Michelle Yeoh if she wanted to, but she chose to play that race extremely demure and understated rather than taking the epic generational victory lap she could have. In the couple speeches she gave, it sounded like she didn’t even want the Oscar.
Meanwhile, Yeoh (who I love, and who I’m happy has an Oscar) tiptoed right up to the line of bad taste with the OTT campaigning she did.
I get the feeling Emma Stone’s next Oscars will be as a producer. Her streak of nominations (and wins) reminds me of Olivia de Havilland in the 1940s: five noms, two wins, and that’s all she wrote.
This was my kind of article thanks Claudio,my thoughts
You state no-one had been nominated in their 90's,Dame Joan Collins has a film out this year playing Wallis Simpson,I know she isn't a master thespian and it's very doubtful but some people on other blogs are whispering her name.
Spacey when hell freezes over.
Caine very unlikely I would've given him a 3rd for Youth
Hopkins possible if he keeps working and is his win that controversial,it was only controversial if you bought into that 2020 narrative which i didn't,the win was very well deserved.
Waltz I really hope,he has no range at all,the first win yeah fine cos we didn't know him but not the 2nd win that should have gone to Hoffman or De Niro.
Brody insufferable when he wins so praying that's it for him,I don't think he really deserved the 2nd,I would have gone with Stan and it was a shame Daniel Craig was snubbed.
Swank if she got a good role playing to her strengths or something that's the opposite I could see her returning and yes i'd have nominated her for Conviction over Lawrence and The Homesman over Pike.
Renee I have found it odd that Renee got a huge welcome back from fans and her Oscar peers and did virtually nothing with it,no auteur director supporting roles,no interesting star vehicles just silly Bridget sequels,I wish she'd work more.
Lange not happening,I thought Mary Tyrone might bring her back and if released could've,I could have seen her slipping into the 2023 or 2024 line up ousting Bening or Gascon.
Ali most definitely somewhere down the line though Colman Domingo seems to be sucking up a lot of roles Ali might've played.
Hoffman nope,rewarded enough and doesn't do Oscary projects anymore.
Field should have had a 3rd already beating the terrible Fantine performed by Anne Hathaway as if she's in a soap commercial.
Wiest it'd be nice but very doubtful
Fonda they didn't nomnate for her stellar role in Youth which i'd have handed her a 3rd Oscar for but time will tell,maybe she' breaks the 90 odd year olds non nomination.
Emma is in her Meryl years but personally I think she should perhaps switch it up a bit and do something really commercial without wigs & costumes etc,just be her.
Hanks could happen but his taste became very iffy after CoVid for some reason,his Gepetto was woeful.
Foster yes and yes and triple yes,one of my alltime favourites and she's been away from the winners circle long enough to feel like it's time for a 3rd,is working steadily and really bringing it and her peers love her plus she's a darling now on the press circuit open happy and honest.
Cate B I assume she doesn't want it just yet has at least 20 odd more good years in her.
Denzel it's won't be happening for the next few years yet,he's filming Hannibal this summer which doesn't sound very Oscary.
De Niro sullied his legacy and do you really think he was worthy for The Irishman or did we see a different film,I thought he was that films weak spot despite some good moments.
Penn could he win a 4th or is he done now.
I would like to see Julia Roberts,Sissy Spacek,Julianne Moore,Nicole Kidman,Brad Pitt,Leonardo Di Caprio,Al Pacino and Kate Winslet win a second,does anyone agree that 1 doesn't do their careers justice.
I am stepping out on a limb to predict a third Best Actress Oscar for Sally Field next year in the Netflix adaptation of the popular novel Remarkably Bright Creatures.
Agree DK that Yeoh stepped up to the line with her campaigning - i remember reading about a tweet she put out showing Blanchett's face saying 'someone who looks like this has 2 oscars already' then a pic of her own face saying 'someone who looks like this has none' - then deleted it. Seems against the rules but who am I?
MrRipley - most DEFINITELY Sally Field should have 3 already. Lincoln should have been a third for Field and Spielberg to go with Day-Lewis' third.
Fences should have been Denzel's third (and I may be in the minority but i even liked him in Tragedy of Macbeth - JUSTICE FOR KATHRYN HUNTER!!)
PLEASE PLEASE let Long Day's Journey Into Night see the light of day and award Lange her third Oscar!!
On a side note - i LOVE LOVE the old plays and would LOVE to see a new Mourning Becomes Electra - love the play and Rosalind Russell in the original.
But i digress haha
Frank Zappa -- I was thinking of acting awards for this piece, but you're right that Stone's next Oscar might be as a producer. I SAW THE TV GLOW, PROBLEMISTA, A REAL PAIN, and others make for a very promising start for her career behind the scenes. Looking at IMDB, she's producing an Emily Mortimer directorial effort starring Alison Oliver and Yura Borisov, a Michael Diliberti project, and Jesse Eisenberg's next feature with Julianne Moore in the lead.
Mr Ripley79 -- Glad you enjoyed it. Your comment also made me wonder how many times I'd have actually given three acting Oscars to the same performer. Looking at my endless spreadsheets on Oscar eligibility, I'd actually have done this with nine people: Isabelle Huppert, Marion Cotillard, Tilda Swinton, Vanessa Redgrave, Maggie Smith, Paul Newman, James Mason, Katharine Hepburn, and James Cagney.
Finbar McBride -- Considering the film is going to come out in May, and there don't seem to be plans in place to give it a theatrical release, I'm afraid for her chances. But it does look interesting. I admit I'm not in the "Field deserves three" camp, mostly because I don't like her 1984 win. Maybe if I convince myself she won her second for STEEL MAGNOLIAS or something.
Tony L -- Washington is my pick from the 2016 nominees, too, and I agree that he's quite good in MACBETH. And, indeed, JUSTICE FOR KATHRYN HUNTER!
Oooh - Claudio - i'm curious about that (3) you gave to Isabelle Huppert - i LOVE her!! 8 Women, The Piano Teacher, Elle, so many many more!!
FYI - i flew to Australia to see The Maids when Cate Blanchett and Isabelle Huppert performed it together. Fabulous!!
Tony L -- Oh, that's so exciting. What did you think of that staging? I've heard conflicting things from friends and acquaintances who saw it, though they mostly agree that Debicki was a surprising MVP as a "miscast" Madame. I love Genet, including THE MAIDS, and have even worked on a show derived from his writing. Such amazing theater.
Regarding Huppert, the data I shared is about my lists based on Oscar eligibility (I also have incomplete lists based on the general US release calendar and world premieres). That means Huppert wasn't accounted for 2002 Best Actress as THE PIANO TEACHER's American distributors didn't even bother to submit the film for consideration. Anyway, these are the wins and nominations I'd have given Huppert over her career, according to Oscar eligibility:
1977) Best Actress, THE LACEMAKER
1978) Best Actress, VIOLETTE
1981) Best Actress, LOULOU (winner)
1989) Best Actress, STORY OF WOMEN (winner)
1999) Best Actress, SCHOOL OF FLESH
2002) Best Supporting Actress, 8 WOMEN
2014) Best Actress, ABUSE OF WEAKNESS
2016) Best Actress, THINGS TO COME
2016) Best Supporting Actress, LOUDER THAN BOMBS (winner)
Some award-worthy performances of hers I love that never appear in the Oscars eligibility lists include THE WINGS OF THE DOVE, ENTRE NOUS, LA CÉRÉMONIE, THE PIANO TEACHER, GABRIELLE, WHITE MATERIAL, IN ANOTHER COUNTRY, and A TRAVELER'S NEEDS. And I still need to see a lot more from Huppert's filmography. Am particularly eager to dive into her collaborations with Schroeter.
@ Cláudio
Of course, it just occurred to me that if AMPAS falls out of love with Stone as an actress the way they did with de Havilland, at least her producing career is thriving. And then I realized she'll probably produce herself into at least three more nominations, and potentially another win.
I've acted in Les Nègres, Haute Surveillance and Le Balcon—not in an all-male Les Bonnes, but I wish. Love Genet and all his writing.
I mean, anyone can win with "the right project," but I get the arguments here. Even on paper, I predicted Hopkins for One Life and Waltz for Frankenstein right off the bat. Brody and Zellweger were written off for pretty much the entire time between their wins. After Madigan's win, I'm far less likely to downplay Field, Lange, and Wiest chances winning in their late 70s and they are all working as actively as they can. But the answer is likely Stone, especially since, unlike most of the winners here, both of her wins were in multiply rewarded projects and she just had another acting nomination. I doubt that AMPAS will "make her wait" too long, nor should they, as that clearly didn't work with Foster (who might have defeated Lange for Nell if it wasn't "too soon" to give her a third), Hanks (similar argument with Cast Away), and probably most of the others who won both within a decade.
I’m really grateful to McDormand and Penn for breaking this taboo—for 50 years the assumption was that only people named Bergman, Hepburn, Nicholson, Streep or Day-Lewis were allowed to have a third Oscar. And if you weren’t first in line in some universally agreed “greatest of all time” list, you were not worthy.
How is Hopkins' win controversial? It's the best Best Actor winner of the century! I have never seen anybody dispute the excellence of that performance.
I think De Niro's age renders it unlikely, but yeah - that stretch from 1974 to 1983 could've been three oscars if the stars aligned.
As a rule, though, I don't like threepeats - there are so many great performances. Like, wouldn't Oscar history be better served if Emily Watson or Saoirse Ronan or Carey Mulligan had two of those Oscars. I'm actually the opposite of DK - if it has to happen, I only want certified legends to get it. Obviously, intelligent people can disagree!
So I'm not particularly disappointed that Blanchett or Washington don't have that third Oscar, despite being competitive for it.
My issue with the “legends only” thing (aside from the fact that McDormand and Penn are giants of their generation) is Meryl Streep.
For at least a decade, the conversation insisted that Streep deserved a third Oscar: The question was “Which one of these flimsy dramas/biopics will be the one to do it for her? Which year will be soft/weak enough to allow a coronation? Who (Viola Davis) can be pushed aside the easiest to make room for this item on our to-do list?”
When you design races on the premise that [blank] needs a third Oscar, you get wins for work like Murder on the Orient Express, As Good As It Gets and The Iron Lady. Those aren’t bad performances but they represent some of the weakest wins in their categories in their respective decades.
I don’t think we should put our thumb on the scale to get “worthy” people third Oscars and I don’t think we should put our thumb on the other side of the scale to stop people we don’t consider “worthy” from winning one. Just let the years play out.
@DK I totally agree with that last statement
If the'd have hung on for Bergman wouldn't a 78 victory be a better representation of her career.
If they'd have waited till 2002 for Jack's 3rd wouldn't About Schmidt be a better 3rd Oscar vehicle option.
Only Day Lewis#s 3 is a representation of what he can do across the decades and while I would've had him win a 3rd for Phantom Thread rather than Lincoln his 3 wins are still the best.
I find France's 3 wins came at the expense of superior performances in their respective years,I disagree more with that 2nd win where I think everyone inc the non nominees are superior to her that year,I like her 3rd win the best.
Penn's 3 are very good but it saddens me that murray couldn't bst him in 2003 or Rourke in 2008,all 3 then would be osacr winners
If De Niro hadn't been part of such dreck in the last 20 odd years maybe the give him a 3rd narrative might have taken hold in 2012 or 2023.
Denzel is the one person i can see getting a third next but he keeps saying he's retiring.
96 belongs to Blethyn or Watson,2017 to Ronan or even Streep,The Post would have been a better 3rd win.
All this talk of 3rd's and some are without a first Sigourney,Ruffalo,Dafoe,Ed Harris,Pfeiffer,Annette and Glenn and even legends like Marlene Clift Garbo Monroe never won or were nominated.
From this list, I feel most likely is Denzel. The problem with him is if he is able to be in best picture contender since lately the best actor is so tied to best picture contender. I know he won in non best picture contender but that was 20 years ago and the specific circumstance enabled him to win. The academy has changed so much but if anybody can buck the trend, it will be Denzel.
As for Blanchett, I feel like she needs to do it soon since we know that leading roles quickly dry up once actresses reach a certain age. Obviously, she is very respected so she can still do it even in her twilight years if she gets the plum role.
As for Emma Stone, I am not sure I agree with the assessment that she is like Streep or Lange in the 80s. They were nominated in middling acting vehicle (more so Lange than Streep) while Stone is nominated in best picture vehicles. I really like Stone but I am always worried when actors are nominated frequently in short succession. I always feel like the obsession can die as quickly as it rises. I hope it doesn't happen to Stone as I think she is a pretty versatile movie star with her "Emma"-ness sprinkled in her performances.
In general, I don't really care for 3rd Oscar, I feel like it's just bragging rights for the stans..lol. Since performances are subjective, I think 2 Oscars for each actor is more than enough and Academy has a rule that once you won 2 Oscars, you can't be nominated competitively and will be honored with special achievement based on calculated votes :) Like I think Kidman should win a 2nd Oscar but I don't mind if she never wins again if it means these overdue actresses "insert name here" win their first!
@DK - Yeah, that's a fair assertion re: Streep, I can't pretend otherwise. In the end, there are more great performances than Oscars so I tend to weigh on the side of spreading the wealth.
Like if Christoph Waltz gets a third Oscar, I would be VERY cranky, regardless of it's actual merit.
And honestly, it's not only performances. I was cranky when Lubezki won his third Oscar, despite the fact that he has a career that merits it. I just pretend that he won for Children of Men, Tree of Life and Gravity.
Cate Blanchett losing the Oscar for Tár is just as egregious now as it was when it happened. It increasingly feels like De Niro losing for Taxi Driver or Pacino missing the award for The Godfather Pt 2. It becomes especially infuriating when you take into account Yeoh's recent comments in Berlin about not mixing politics with art when all she did during that Oscar season was politicize the Actress race in order to win. Such an unethical campaign and such a gargantuan robbery.
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I lol'd at Claudio saying Renee Zellweger was better in Mad about the boy than her oscar wins. Truth be told, she's just exquisite being Bridget Jones. Her first nomination is still my favorite, perhaps second after Chicago. She could have been a rom com queen like Julia Roberts on Reese Witherspoon. Any way, I'm glad she's chill just as she is.