The Highs & Highs Of The 2025 Oscars
Conan O'Brien is good. And other thoughts.
Right before going to sleep last night, I had this brilliant idea. The Oscars were actually fun, everything went (almost) swimmingly and Conan O’Brien earned a Nobel Peace Prize. So, instead of doing the Winners & Losers of the event, what about we just do the Winners? And of course, I could still be snippy and passive aggressive when the time calls for it.
Well, it was such a great idea that I had it twice. Once last night and also a year earlier.
Oscars Winners & Winners(?)
To be fair, it’s been a long year between the “political divide” as so many people safely put it yesterday and the fact that I had to watch Emilia Pérez, which I’m still recovering from. So, yes. I’m repeating myself. But, you’re still reading, so you’re in the pits of hell right there with me.
Anyway, here’s what I liked … and here’s what I facetiously liked. Let’s get to the winners!
Netflix, Amazon Prime, Disney+, Max
The big winner of the night—other than Anora, but we’ll get to that later—is every streaming service that wasn’t Hulu. Midway through the Best Actress award and with only Best Picture left to go, Hulu decided that that was enough and (accidentally … or maliciously) turned off the show for everyone streaming. A “Thank you for watching!” pop-up was all that was left along with an error message and literal screams from my Oscars party. I quickly found a (kind of legal?) way to stream the end of the show, but many missed out on the stunning Mikey Madison win and the following Best Picture award.
What a fuck-up. I never want anyone to get fired—well, that’s not totally true—but I would be stunned if there wasn’t a person or two losing their jobs tomorrow at Hulu. Like, how do you not prepare for the show to go long? It goes long every damn year. It’s a running joke in every Oscars show since the dawn of time. Right before the dinosaurs were obliterated, they were discussing how they could cut down on the three-hour-and-forty-five-minute Oscar runtime. Well, it was very funny. To me at least.
Ben Stiller
I don’t want to name names, but a friend of mine (she knows who she is) despises Ben Stiller. Why exactly? Because he has bad vibes or something? Because he’s kind of dick-ish in Along Came Polly?
Well, it was a tough night for her as Ben Stiller was one of the big winners of the 2025 Oscars despite his day job of directing and executive producing a television show.
The above bit while presenting Production Design is just a good old-fashioned sight gag that won over the audience almost immediately. It all took a little over a minute, centered the award to come and showed off a bit of athleticism. Also, the Knicks won last night, so congrats to Stiller for that as well.
Sean Baker & Mikey Madison
It’s weird when you’re agreeing with the Oscars but Anora and Oppenheimer (last year’s Best Picture winner) were both some of my favorite movies from their respective years. Oppenheimer was an awards behemoth between its bevy of beloved actors to its “great man” premise to the “it’s time” run for Christopher Nolan, so it’s not as surprising, but Anora is something different.
As director Sean Baker mentioned, Anora is a true independent film starring a relatively unknown actress centered on sex work and a FRAWD green-card marriage, which becomes a slapstick comedy halfway through. It would be a shocking win for an Academy of 10 years ago, but makes a bit more sense with the influx of international and younger voters.
Still, for a movie like this to win five of its six Oscar nominations—poor Yura Borisov—is remarkable and a hell of an achievement for Baker. It seemed like Best Picture was coming, but Baker also became the first person in Oscars history to win four Oscars in one night for the same movie. That’s insane stuff.
The real Anora upset was Mikey Madison besting Demi Moore and Fernanda Torres at the end of the night for Best Actress, which really shows how strong the support for the movie ended up being. At just 25 years old, Madison is the third acting winner (after Jennifer Lawrence and Ariana DeBose) to be born in the 1990s and can basically do whatever she wants to now. I hope she doesn’t get pigeonholed and it seems like she has great taste and a compelling starpower. All good things for the future of movies.
Dogs
Flow won Best Animated Feature (it’s centered on a cat but there’s a dog in it) and multiple winners thanked their dogs. That’s more than enough for me. There was no Messi this year, but hopefully he’ll be back next year.
Kendrick Lamar
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"Well, we're halfway through the show, which means it's time for Kendrick Lamar to come out and call Drake a pedophile."
That’s another win for Kendrick Lamar, who’s now halfway to an EGOT for embarrassing Drake. Oscars … check. Grammys … obvious check.
Excited for Kendrick Lamar’s Broadway show, which also calls out the Canadian rapper in hiding.
BUM BUM BUM BUMMMMMMMMMMMM
The best part of The Brutalist, a great movie that you should see if you have four hours to kill, is the score. Starting off the movie with a bang, this score is one of my favorites in recent years and deservedly beat out the field for Best Original Score.
For a movie made for a relatively small amount, the score lends some extra gravitas and pushes the story to its inevitable conclusion. Daniel Blumberg more than deserved plaudits for this one, and I’m happy the Oscars got this right.
Timothée Chalamet
Sure, Timmy didn’t win an Oscar, but he had two movies nominated for Best Picture, has been nominated for Best Actor multiple times before the age of 30 and got the Adam Sandler Seal of Approval. He’ll be just fine.
After a press run for the ages, you can’t say that Timothée Chalamet didn’t put his all into trying to win the big one. It’ll come. I’m not worried about it.
Chalamet’s speech after his SAG win became a bit of a hot-button topic, but here’s my take: It fucking ruled.
“I can’t downplay the significance of this award because it means the most to me, and I know we’re in a subjective business, but the truth is, I’m really in pursuit of greatness. I know people don’t usually talk like that, but I want to be one of the greats. I’m inspired by the greats. I’m inspired by the greats here tonight.
I’m as inspired by Daniel Day-Lewis, Marlon Brando, and Viola Davis as I am by Michael Jordan, Michael Phelps, and I want to be up there. So I’m deeply grateful. This doesn’t signify that, but it’s a little more fuel. It’s a little more ammo to keep going. Thank you so much.”
To have someone in the limelight who cares this much about making good stuff and working with the best in the industry is a breath of fresh air compared to a lot of movies I see every year. Chalamet has tremendous taste and will be right back in the Best Actor race, perhaps even next season for Marty Supreme.
Also, to be fair, I’m perfectly fine with Adrien Brody winning (shoutout to Georgina Chapman for some gum help), despite his pretty terrible and rambly speech. Honestly, Brody would’ve been my pick of the five nominated, even if I was rooting for Chalamet for the fun and chaos of it all.
John Lithgow
This Guy
“Our hearts go out to those who have lost their homes. And I’m talking about the producers of ‘Joker 2.'”
What a delivery from Los Angeles Fire Department captain Erik Scott. If he ever tires of saving lives, the man could be a stand-up comic. Perfect joke and Conan O’Brien’s bit of having firefighters read some cruel jokes is another feather in his cap. Just look at these reactions:
Beautiful stuff.
Wicked: For Good
Wicked won two Oscars. I fear Wicked: For Good is about to win Best Picture. We’ll worry about that in 10 months. For now … good singing!
The Plot of The Substance
The Substance becoming an Oscar winner and awards favorite is crazy. How did this happen? I’m thrilled about it, but jeez. This is not your run-of-the-mill biopic.
No Other Land
“About two months ago, I became a father, and my hope to my daughter [is] she will not have to live the same life I am living now.”
I’ve written about this movie already, but you should check out No Other Land, now an Oscar-winning documentary on the destruction of the occupied West Bank's Masafer Yatta by Israeli soldiers. Outstanding movie that needs to be seen by more people. Kinda crazy that we could get a speech like this on such a big stage. One of the best moments of the night.
Conan O'Brien
The thing about Conan O’Brien is that he’s both a genius and an idiot, which is what makes him so damn perfect for the Oscars. It was somehow his first time hosting and he was more than comfortable to make ballsy jokes whether it be on Russia or Karla Sofía Gascón while also constantly making fun of himself so as to keep the audience on his side.
Conan has been one of my favorite comedians/people for as long as I can remember, so it’s nice to see him get a chance at the Academy Awards and just fucking kill it. From his initial The Substance bit to his opening monologue to his song-and-dance number with a Shai-Hulud/sandworm to showing up with an incredible joke here and there throughout the broadcast to keep the train moving, O’Brien nailed it and seemed to be having the time of his life.
It’s obvious that he actually watches the movies nominated and likes movies (not always the case for some of these hosts). Just look at his Four Favorites. The man knows what he’s talking about.
Conan O’Brien is unbelievable at being Conan O’Brien, and he somehow brought his beautiful nonsense to the Oscars.
Well, we did it and I’m tired. See you next week.
It’s time to start thinking about the 2026 Oscars.