Are Oscar Dynasties Good for Cinema?

Anyone who covers or follows film awards season understands that you inevitably have to talk about more than just the movies. Our initial reactions to the artistic merits of each film quickly gives way to months of conversations about campaigning, messaging, positioning, momentum, and other considerations that have nothing to do with art.

That’s either a necessary evil or part of the fun, depending on how you look at it, but it’s not going anywhere. And sometimes, you’re left with conversations that your film vocabulary is ill-equipped to cover.

I found myself in such a position on Sunday, when “One Battle After Another” star Sean Penn won the BAFTA Award for Supporting Actor, putting him in the pole position to win his third Oscar in just a few weeks. Certain corners of the internet quickly started discussing whether seeing a repeat winner made for a less compelling story than seeing someone else win for the first time.

If you consume any amount of sports media, you’re instantly familiar with this topic. Conversations about the NFL, NBA, and MLB frequently question whether dynasties are good for sports. The query centers around what is more interesting from the perspective of a casual fan with no horse in the race: seeing one team try to stack multiple championships, or seeing more teams get their moment in the spotlight?

I’m of the mindset that, in sports leagues with salary caps and drafts that actively make it harder for teams to sustain success (a very good thing!), nothing is more fascinating than seeing if the Kansas City Chiefs or the Golden State Warriors are capable of sustaining greatness in an environment that’s working against them.

I’d argue that award voting functions similarly.

Timothée Chalamet speaks onstage during the 78th Annual Directors Guild Of America Awards at The Beverly Hilton on February 07, 2026 in Beverly Hills, CaliforniaGetty Images for DGA

I’ve been reading anonymous Oscar ballots every year for as long as I’ve had internet access, and there’s always someone who mentions voting for their second choice because their first choice has won too recently and they wanted to spread the love. I love that sentiment, but it only makes me more impressed when someone manages to win multiple Oscars in a career.

All of which led me to a theory: watching an actor or filmmaker try to win a second or third Oscar is inherently more interesting than watching someone pursue their first. It doesn’t mean the repeat winner is more deserving, or that I’m always rooting for them, but it’s the most compelling storyline that award season has to offer.

Take this year’s Lead Actor race, for example. I don’t feel any real suspense about whether Timothée Chalamet or Michael B. Jordan will get their first Oscar this year — they’ve done too much great work for too long, have decades of runway ahead of them, and if this isn’t their year, then I’m confident another one will be. But I’m deeply curious about whether Leonardo DiCaprio will ever win a second one. It could go either way, but each additional one that he wins will only bolster his status in the pantheon of great Hollywood stars.

Michael B. Jordan at The 16th Governors Awards held at The Ray Dolby Ballroom at Ovation Hollywood on November 16, 2025 in Los Angeles, CaliforniaGilbert Flores/Variety

To be clear, I desperately wish I had someone more charismatic than Sean Penn to make this argument about. (The case for Meryl Streep’s fourth Oscar rolls off the tongue so much better!) And if I was an Oscar voter, I’d be casting my ballot for Chalamet, Benicio del Toro, Amy Madigan, and Jessie Buckley, just because I think they’re the four best performances. But from an audience perspective, I think someone’s quest for Oscars #2, #3, and even #4 creates the best water cooler storyline that we can ask for.

We’ve already seen a few great acting dynasties: Meryl Streep, Jack Nicholson, and Daniel Day-Lewis have each become three-time winners, and the likes of Penn, Denzel Washington, and Robert De Niro could certainly enter that territory at some point. The chase to reach that mountaintop and the celebration that follows are a story that rivals any sports movie that Hollywood could write.

If you read all of that, there’s a decent chance you’re now thinking “that sounds ridiculous and fundamentally opposed to how we should consume and appreciate art.” And I’d find no reason to disagree with you. But I would argue that award shows have never been and will never be conducive to properly appreciating art, and that’s fine! I like to think that any cinephile who cares enough about the Oscars to track them for the 6+ months of award season has a nuanced enough worldview to know that one movie winning Best Picture doesn’t actually make it better than another one.

There’s enough room in the canon of cinema for all the best movies of 2025 to be remembered. “One Battle After Another” and “Sinners” are both great films that deserve to live on as modern classics, and one “beating” the other shouldn’t have any real affect on their legacies.

Leonardo DiCaprio and director Paul Thomas Anderson filming ‘One Battle After Another’ ©Warner Bros/Courtesy Everett Collection

But that caveat only makes me more tempted to sports-ify the Oscars. Once I accepted that pitting great works of art against each other and picking true winners is inherently impossible, I was left with a more clear view of what award shows are in 2026. I see them as fun entertainment products that help keep great movies in the limelight long after their traditional theatrical runs have ended. They create soap opera-like storylines that keep us engaged for months on end and then allow us to neatly crystalize each year of film history.

And, perhaps most importantly, they create a monocultural event that gives everyone a reason to think about movies for a night, no matter how few trips they might have made to theaters the year before.

That’s why I like Oscar dynasties.

Even if Penn and DiCaprio are not my first choices in their respective categories, I don’t see a world in which things would be boring if they won. In the same way that Patrick Mahomes’ quest for a three-peat is enough to make even the most casual football consumer dial into the Super Bowl — either to root for him or against him — living legends chasing repeat wins is great for the Oscars as a TV product, a cultural moment, and just the thing to keep everyone watching as awards season unfolds.