Before the fall film festivals started and before “One Battle After Another” had any preview screenings, an X user named @imovied asked the NBP podcast team about rumors of Sean Penn being a real Best Supporting Actor contender – and if he could really beat out a “beloved contender” like Adam Sandler just like he beat Bill Murray in 2003 and Mickey Rourke in 2008.
Over three weeks later, and with the review embargo for “One Battle After Another” busted, this is now a question we need to take more seriously than ever. Even if Sandler himself slipped from the winning competitive conversation for “Jay Kelly,” there is also Stellan Skarsgård for “Sentimental Value” and possibly Paul Mescal for “Hamnet” as beloved performers with heart-warming narratives – yet we now officially must consider Penn as someone who could spoil them both. But that is not all we have to consider regarding Penn’s return to Oscar season.
Penn won two Oscars a very long time ago in a very different decade, and hasn’t really participated or been in the mix of another Oscar season since. The closest he came was his mid-film extended cameo in Paul Thomas Anderson’s last movie, “Licorice Pizza.” Yet, it was a very small part that made him unnecessary in the film’s awards campaign and story. That is not the case with his next Anderson movie, as there is no getting around Penn in this film as the white-supremacist cop hunting down Leonardo DiCaprio and his family, just as there may be no getting around Penn in “One Battle After Another’s” months of campaigning ahead.
Penn is usually not someone who does much press for his films, but he has at least been part of the premieres and initial junkets leading to “One Battle After Another’s” theatrical release. For now, it can be assumed he will do the same deeper into the season, especially as the film is positioned as a Best Picture favorite and Penn is positioned as a potential Best Supporting Actor nominee, if not winner. At that point, the real ticking time bomb will start to count down.
This is the first time Penn has been part of an Oscar season in this hyper-vigilant, hyper-online, and hyper-hair-trigger era, where any past or present controversies and comments can become a significant story or be pushed as one online. When it comes to Penn, there is no shortage of past off-screen incidents and inflammatory comments that can resurface as a topic of conversation and reheated backlash at any time – the kind that fewer people obsessed over while he was on the way to winning Oscars for “Mystic River” and “Milk” two decades ago.
It took dedicated research last year to dig up Karla Sofia Gascon’s various past comments and controversial beliefs online, and to make that the headline story of the moment before Oscar night. It does not take nearly as much time and effort to look up such issues regarding Penn, from his volatile relationship with Madonna to any number of comments that enraged every political wing at one time or another. And when it comes to the latter issue, that could be what Warner Bros and their pr team has to really hold its breath over.
It is definitely worth wondering how much Warner Bros will lean into the hot-topic political issues and metaphors of “One Battle After Another” – especially in fall 2025, with a voting body that may or may not want to wade into such matters, and with a studio head in David Zaslav who has seemed to lean more in line with the current administration time and time again. But such issues will have to be discussed in some capacity for the next several months in junkets, interviews, and speeches, given how central they are to the movie as a whole. And when they are, the one everyone will expect to give a no-holds-barred comment about the movie and the times it speaks to at some point will be Penn. Then, if and when he does, all bets will be off on who it inspires or outrages and why.
With a months-long campaign ahead, can Penn really be expected to hold his tongue that long before saying or taking aim at something that will spark controversy, and will “One Battle After Another” be helped or hurt by it? Since Penn has never held back regardless of what it means for his career, and regardless of which side gets angry at him for it, any impact on his own Best Supporting Actor chances surely won’t matter to him. But will he be slightly more careful to protect the movie’s own chances, and to keep any blowback from hitting Anderson and his own shot at finally winning an Oscar, or if not, what happens then?
Maybe “One Battle After Another” and Anderson himself will become so undeniable, as the first unembargoed reviews and scores suggest, that none of this will or should make a dent against them. But will it make a dent in Penn’s first Oscar campaign of this very different era – and if not, will history indeed repeat itself in his favor?
On paper, it should hurt that Penn is trying to win a third Oscar before the likes of Skarsgård, Mescal, Sandler, and others can win their first. But when Penn won his first Oscar for “Mystic River,” he was still deemed more overdue than Murray – and then when he won his second for “Milk,” the prospect of Rourke winning his first in a heartwarming comeback role for “The Wrestler” didn’t stop Penn anyway. In any case, in an era where Meryl Streep won her third Oscar for a critically panned movie, Frances McDormand won a second and third Oscar within four years, and Mahershala Ali won two in three years, Academy voters really don’t mind going back to past winners these days.
Nonetheless, this time Penn is facing someone in Skarsgård who is a more consistently active and acclaimed actor than Rourke, who is more of a supporting/character actor than Murray, but has probably ingratiated himself with half the voting body over the last three decades, and who was deemed virtually unbeatable when “Sentimental Value” first broke out at Cannes. And although “Sentimental Value’s” status as a top 3 Best Picture frontrunner took a hit at TIFF, perhaps that makes it easier for Skarsgård to stand out and become a collective winner for the entire movie as a whole, even if the film slips elsewhere.
If Mescal doesn’t go lead for “Hamnet,” he too might be deemed a more heartwarming choice, as a rising star and past nominee taking the next big step forward and boosted by a potential Best Picture winner. Nonetheless, with speculation that “Hamnet” might outright sweep Best Actress for Jessie Buckley, it would need to be a substantial Best Picture leader to get two acting wins – and the likes of “One Battle After Another” and “Sentimental Value” might make that trickier.
Sandler could also reemerge as a threat and sentimental favorite, since he was deemed the best part of “Jay Kelly” even by those disappointed in the rest of the movie. If the industry does still rally around it and boost it back up, as many suspect it will, maybe those same boosters will make Sandler a winning threat again, as all he might need is one big win and speech at a televised ceremony to turn everything upside down.
Would Penn still be imposing and unavoidable enough to sidestep all those narratives and potential dream winners, like he was in 2003 and 2008? He had Best Picture nominees in “Mystic River” and “Milk” to help him back then, yet neither of them won it all. But if “One Battle After Another” does, will that be all the extra help he needs, or will that support just be saved to give Anderson his Oscar in either Best Director, Best Adapted Screenplay, or both?
Penn won his two Oscars in Lead, yet this is his first time competing in Supporting. For this type of role and character, that could be a distinct advantage, as the Best Supporting Actor category is filled with recent winners who played antagonists, if not outright villains – from Javier Bardem to Heath Ledger, Christoph Waltz, J.K. Simmons, Robert Downey Jr., and arguably Sam Rockwell. In that context, a fascist-coded lawman like Penn’s Steve Lockjaw would fit right in.
Still, giving Penn a third Oscar for such a character, even in what may be an Oscar juggernaut, won’t be cheered as loudly as a win for someone like Skarsgård, Mescal, or Sandler would be. But the Penn of the 2000s had no problem spoiling such dream finishes, albeit in a very different era. Will competing in this current era and all its landmines for the first time make it harder for him – and will he make it harder for himself off-screen by stepping on new landmines, as he tends to do?
Now that “One Battle After Another” and Penn are officially and undeniably in this race, waiting for Penn to say or do something controversial – and waiting for any number of past controversies to be relitigated all over again – could be the 800-pound shadow hanging over this entire campaign, if not the whole season. In a promotional gauntlet for this type of movie in this type of climate, involving this type of actor and public figure, it may be unavoidable. But will Penn powering through it to win again be just as unavoidable as it was all those years ago, anyway?
Who do you think is getting nominated for Best Supporting Actor? Do you consider Sean Penn to be the frontrunner? Are you planning to see “One Battle After Another” this week? Please let us know in the comments section below and on Next Best Picture’s X account and check out the team’s latest Oscar predictions here.
