Although some dubbed the Oscars as the most ‘boring’ in history, some awkward moments took place between awards – from scathing remarks to strange outfits and on-stage falls
The Oscars are often a place for unforgettable blunders and slip-ups, and the 97th Academy Awards was no exception.
From scathing remarks from host Conan O’Brien, to funny red carpet recreations, the ceremony delivered its usual night full of controversies. The event closed off the awards season with Sean Baker’s dramatic comedy Anora emerging as the night’s big winner, taking home five Oscars, including Best Picture and Best Actress for star Mikey Madison.
The ceremony began with a heartfelt tribute to Los Angeles, which had suffered several wildfires a few months ago. It was then followed by a few nervous chuckles while O’Brien gave a scathing opening monologue.
After a few swipes and a recreation of one iconic film, the night appeared to be a roaring success. The Daily Star have compiled a list of the wildest head-turning moments through out the night.
Adam Sandler storms out
Not one for dressing up, Adam Sandler entered the Dolby Theatre in Hollywood, California, in his usual attire of a sweatshirt and shorts. Sandler quickly became a viral sensation when social media fans pointed out his famous hoodies.
At the Oscars, Sandler showed this off and became the butt of O’Brien’s joke. He showed off some headshots of attendees, before mentioning how everyone was “properly dressed”, before pausing awkwardly.
The camera turned to Sandler, sat in a blue hoodie with basketball shorts. “Conan. What’s up my brother? What’s going on, man?” Sandler said, before O’Brien asked: “Adam, what are you wearing?”
“What are you doing right now?” Sandler threw back, as O’Brien repeated: “I’m asking you what are you wearing?”
Sandler responded: “Nobody even thought about what I was wearing until you brought it up!” as the crowd laughed.
“You’re dressed like a guy playing video poker at 2 AM, Adam,” O’Brien added, as Sandler insisted: “You know what, I like the way I look, because I’m a good person.”
He got up to leave with O’Brien pleaded with him to stay. They exchanged a few words, before Sandler added: “You are all welcome to join me for a game of five-on-five basketball at Veteran Park tonight. Midnight tip-off. The guy from Nosferatu, he’s on my team.”
He then approached Timothee Chalamet and said: “And one more thing, CHALAMET!” while giving him a hug before leaving to applause.
Demi Moore fumes
Awkward clapping appears a necessary evil at the Oscars – especially for actors who miss out on awards. This appeared true for none other than Demi Moore.
She appeared crushed as Mikey Madison beat her to the coveted Best Actress award at the 2025 Oscars, on a night when Anora dominated with five wins including Best Picture.
Demi had appeared a front runner after a successful awards season and the admission that she had never won before this year. Demi could be seen with a clenched jaw as her name wasn’t called, but she did appear to say “nice” to herself as she applauded Mikey’s big win.
She was up for her movie, The Substance, but missed out to Madison, who portrays an escort in Anora, an independent film with a $6million budget for which Sean Baker won Best Director.
Madison did acknowledge Demi along with her fellow nominees in her acceptance speech. “I also just want to recognise the thoughtful, intelligent, beautiful, breathtaking work of my fellow nominees. I’m honoured to be recognised alongside all of you.”
Halle Berry and Adrien Brody recreate controversial kiss
As if Halle Berry’s stunning sequin gown wasn’t enough, she took everyone by surprise as she playfully interrupted Adrien Brody’s red carpet interview by leaning in to steal a kiss from him.
It was a reference to their on-stage kiss from Oscars 2003 when Brody, fresh off his Best Actor win for The Pianist, stunned the audience – and world – by kissing Berry on stage.
Halle approached him, turned to his wife and said: “Sorry Georgina but I gotta do it.”
The incident took place on the red carpet before the event and instantly went viral. One X user wrote: “Why do people in Hollywood act so weird.”
Another added: “Only place where a wife claps as another woman kisses her husband.”
Kylie and Timothee share a kiss
Lovebirds Kylie Jenner and Timothée Chalamet, seated in the front row, were caught on camera as they shared a kiss during a private moment.
The pair, who have been romantically linked since April 2023, often accompany each other to glamorous award shows. This time, however, the decided to ditch a grand entrance together and simply meet up inside.
Kylie has not been seen publicly since the death of her hair stylist and close friend, Jesus Guerrero.
“Sleeping has been the hardest,” Jenner, 27, revealed via an Instagram Story Friday alongside a screenshot that showed she had been on the phone with makeup artist Ariel Tejada for over seven hours.
Timothee did not pick up and Oscar for his portrayal as Bob Dylan in A Complete Unknown.
Adrien Brody ‘spits gum’ at guests
Brody was slammed over a “disgusting” act as he won his second Best Actor Oscar at the 2025 ceremony on Sunday.
The actor bagged himself the award for his role in The Brutalist. However, as the star was walking up the steps to the stage, he turned around, took his gum out of his mouth and threw it to girlfriend and Harvey Weinstein’s ex Georgina Chapman, 48 – much to viewers’ disgust.
Chapman ran up and caught the gum before he made his way on stage. He said to viewers: “Winning an award like this signifies a destination and something my character references in the film.
“But to me, it’s also, beyond the pinnacle of a career, it is a chance to begin again and the opportunity to hopefully be fortunate enough so that the next 20 years of my life, I can prove that I am worthy of such meaningful, important and relevant roles.”
He thanked Chapman and the two children she shares with jailed Weinstein, saying: “I know it’s been a rollercoaster. Thank you for accepting me into your life.”
Conan O’Brien mocks the guests
Not one to hold back, O’Brian made many scathing remarks to guests in the audience. One particular dig was at the recent drama between Drake and Kendrick Lamar.
“Well, we’re halfway through the show,” O’Brien began after a break, “which means it’s time for Kendrick Lamar to come out and call Drake a paedophile.”
This was in reference to the Superbowl performance which saw Kendrick make wild remarks about Drake in front of a huge audience.
Conan paused for a moment before adding: “Don’t worry, I’m lawyered up.”
Ben Stiller falls on stage
Stiller appeared to suffer a huge mishap while presenting an award on stage. Parks And Recreation star Nick Offerman was on-hand narrating the ceremony.
He introduced him once, only for nothing to happen. It did it again when he failed to materialise the first time.
At that point Ben began to be lifted onto the stage from underneath with the help of an elevator, only for the machine to stall. The audience exploded in laughter.
Ben stared out at them stony-faced, visible only from the chest up due to being partly suspended underneath the stage. From that position, he started presenting the award.
“It is a field [production design] where the slightest miscalculation can lose the trust of the audience and humiliate the performers onscreen,” he read seriously while clambering out of the lift.
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Source: Celebrities - dailystar.co.uk
