Every year, the Oscars promise glitz and prestige, but what really keeps viewers glued to the screen are the unexpected moments in between the awards.
From quick-witted jokes to nostalgic reunions and memorable jabs, the Oscars 2026 had it all. But here are the five best moments that truly stole the show!
1. Conan Goes All In With A Chalamet Jab
Conan O’Brien came out swinging when he opened the 2026 Oscars at the Dolby Theatre with a monologue that moved at lightning speed. The host fired off joke after joke, and nothing seemed off-limits. The most memorable one has to be when he poked fun at Timothée Chalamet’s ballet and opera controversy, landing a cheeky jab that had the crowd roaring. From there, O’Brien widened his target list, taking cracks at Sean Penn and Netflix boss Ted Sarandos.
Related: Oscars 2026: 5 Biggest Snubs That Shocked Everyone at the Academy Awards
2. “It’s a Tie!” Kumail Nanjiani Handles a Rare Oscars Twist Like a Pro
Meanwhile, the 2026 Oscars delivered genuine suspense when the Best Live-Action Short Film category ended in a tie; something the Academy hadn’t seen in 14 years. Presenter Kumail Nanjiani opened the envelope and quickly realized the moment was about to get unusual. Looking surprised but amused, he told the audience, “It’s a tie. I’m not joking.” Naturally, the announcement took the crowd by surprise as they tried to process what was happening.
In case you missed it: Oscars 2026: Complete List of Winners
3. The Two Annas Recreate a “Devil Wears Prada” Moment on the Oscars Stage
Fashion and film collided in the most delightful way when Anna Wintour and Anne Hathaway stepped on stage together. As we all know, Hathaway played Andy Sachs in the film ‘The Devil Wears Prada,’ the aspiring journalist who lands a job at the fictional fashion magazine, and the iconic film was inspired by Lauren Weisberger’s novel about working for a demanding fashion editor. Naturally, seeing the real-life Vogue powerhouse standing beside Hathaway instantly brought that world back to life.
4. Downey Jr. and Evans Deliver a Marvel Reunion
Marvel nostalgia took over the Oscars stage when Robert Downey Jr. and Chris Evans reunited, instantly bringing back their classic Avengers chemistry. Downey Jr. began by praising screenwriters and calling scripts the driving force behind every film. However, Evans quickly cut in with a joke, asking what his co-star had gotten him for the 14th anniversary of The Avengers.
Eventually, Evans revealed he had gifted Downey Jr. a signed copy of the ‘Avengers‘ script, while Downey Jr. admitted he gave Evans nothing more glamorous than his valet receipt. At one point, Downey Jr. even handed Evans the sparkly underwear worn by Channing Tatum in Magic Mike. The funniest part was when Tatum, from the audience, shouted that he would need it “for work later.”
5. Jimmy Kimmel Returns With Trump Jokes and CBS Jabs
Kimmel made a surprise return to the Oscars stage and quickly did what he does best: cracking jokes. While presenting awards during the ceremony, the four-time Oscar host joked that he was actually filling in for Conan O’Brien. According to Kimmel, the host had stepped outside to get some air and was instantly “incinerated by the sunlight.” Well, all thanks to his famously pale skin.
From there, Kimmel went into his signature-style political humor. He took playful digs at Donald Trump, joked about Melania Trump’s upcoming Amazon documentary, and even threw in a jab at CBS. Even so, he managed to keep the mix of punchlines with genuine respect for the documentary nominees being honored.
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