The 2026 Oscars was one to remember on Sunday, with Conan O’Brien returning for his second consecutive year as host and presiding over a night filled with so many surprise inside the Dolby Theatre in Los Angeles. 

It was one of the most exciting nail-biters in recent years, as only one of the acting categories was predictable — best actress winner Jessie Buckley for “Hamnet.”

Going into the night, the other races were a toss up, including a best actor face-off between Michael B. Jordan and Timothée Chalamet, and a best picture race between “Sinners” and “One Battle After Another.”

The “Best Supporting” actor and actress battles also had no clear frontrunners entering the evening, featuring Stellan Skarsgard, Sean Penn, Jacob Elordi, Teyana Taylor, Amy Madigan, Wunmi Mosaku, and more. (Penn and Madigan ultimately won).

Here are the best and worst moments of the night.

Best – Conan O’Brien’s opening

O’Brien’s monologue had a nice blend of goofy jokes (“Between ‘Hamnet’ and ‘Bugonia’ it’s been a big year for movies that sound like off brand lunch meat”) and sharp zingers (pointing out how no British actors were in the Best Actor race for the first time in years, but, “a British spokesperson said said ‘at least we arrest our pedophiles’”).

He also got in a timely jab at Timothee Chalamet for the “Marty Supreme” star’s viral comments about opera and ballet (“I’m told there’s concerns about attacks from both the opera and ballet communities”). The host concluded with an earnest salute to films for celebrating “global artistry” and “optimism” during a fraught time in the world. The comedian hit all the right notes.

Worst – the Leo moment in the monologue

O’Brien’s only “off” moment in the monologue happened when he cut to Leonardo DiCaprio in the crowd, and commented on how the “One Battle After Another” star is frequently the subject of memes.

“Let’s make a new meme with Leo, right now! That feeling when you didn’t agree to this,” O’Brien said, as the text came up onscreen. Sure enough, DiCaprio didn’t look too thrilled.

The joke was weak, it felt like it was written by a member of O’Brien’s writing staff trying too hard to appeal to Gen-Z.

Best – Amy Madigan’s chaotic speech

Madigan took home her the first Oscar in her long career, for her supporting role as Aunt Gladys in “Weapons.” The actress, 75, went to the stage cackling like the Joker, then gave a rambling speech with amusing asides. Madigan, who wore a pantsuit, mentioned how she tried to come up with her remarks while she was in the shower shaving her legs. “And I’m wearing pants, so I didn’t need to do that!”

Did we need to know that? Absolutely not, but Madigan’s oversharing was charming. She wrapped up with a sweet nod to actor Ed Harris, who she’s been married to since 1983. “He’s been with me forever and that’s a long ass time!”

Worst – weird sound editing

The sound went haywire in several instances over the course of the night, including getting too aggressive in bleeping out the cursing. It notably happened after “Frankenstein” costume designer Kate Hawley took home the deserved Oscar for that category. When she gave her speech, she thanked, “My family who put up with a lot of sh-t.” The sound cut out for an overly long time, not just censoring the word “sh-t” but taking out an entire sentence of her speech.

Not only is it not cool, but it also draws more attention to someone dropping a curse word, rather than smoothing over it.

Best – Conan’s YouTube bit 

O’Brien did a bit mocking how the Oscars will air on YouTube starting in 2029. As the comedian started saying “I’ve been assure they won’t change,” he got interrupted by a jarring fake commercial featuring Jane Lynch – mocking how YouTube ads often burst in, at inopportune moments.

The “commercial” faded out, and the Academy Awards host said “sorry about that, but like I said, I don’t think this will change the Oscars at all –” before Lynch interrupted with another fake ad. The bit was amusing, accurate, and didn’t overstay its welcome.

Worst – A rare tie 

Kumail Nanjiani, who was presenting the category of “best live action short film,” paused as he was reading off the winner. “It’s a tie. I’m not joking, it’s actually a tie,” he said. There was a brief silence, as everyone wondered if this was a “La La Land / Moonlight” snafu.

The winners, “The Singers” and “Two People Exchanging Saliva,” both gave speeches. In between them, Nanjiani improvised a solid joke on the spot (“Ironic that the short film Oscar is going to take twice as long!”)

A rare tie has happened six times in Academy Awards history. You’d think they’d build in some kind of fix to prevent such confusion from happening. 

Worst – An anticlimactic end to the “Supporting actor” race 

This year was an especially stacked “supporting actor” category. Hollywood veterans Stellan Skarsgard, 74,  and Delroy Lindo, 73, have both been turning in great work for decades. Both have also been criminally under appreciated on the awards circuit, as both were first-time nominees. Jacob Elordi also gave one of the year’s best performances in “Frankenstein.” Any of them would be worthy winners. And yet, the choice was Sean Penn, who didn’t show up.

He’s won Oscars before, so there’s not much of an argument that it was “his time” over Skarsgard or Lindo. (And, his “One Battle After Another” character was cartoonish, so there’s not much of an argument that it was clearly the best among these options).

Kieran Culkin, who presented the award, quipped, “Sean Penn couldn’t be here this evening, or didn’t want to,” and O’Brien later remarked on Penn being “a no-show.” For such a strong year in this category, it ended in a flop.