The Oscars have been Hollywood’s biggest night since 1929. What started as a small, private dinner with just 270 people has now metamorphosized into a spectacle, some controversy aside. From Marlon Brando rejecting his award in 1973 to Hattie McDaniel making history as the first Black Oscar winner in 1940, the Oscars have always been full of surprises, and not all of them have been scripted, rarely any for that matter.
While the night is all about celebrating achievements in film, it’s also notorious for the occasional mix-up. Let’s take a look at ten of the most cringeworthy Oscars moments – because the best part of live TV is when it doesn’t go as planned.
10. Eminem is seventeen years too late (2020)
The Oscars are not without their fair share of surprises, but one moment that left many confused was Eminem’s surprise performance of Lose Yourself in 2020. Yes, the same song that won him the Oscar for Best Original Song back in 2003 for Eight Mile.
Eminem, however, did not show up to accept the award back then. Why the big moment 17 years after the song won an Academy Award? Eminem skipped the 2003 ceremony because he didn’t think he’d win and was busy at home with his daughter. He recalled being half-asleep when his collaborator Luis Resto called to tell him he’d won.
Resto did the honors that night. It was rare for a nominated act not to perform, so we never got to see Eminem on that stage – until 2020.
While fans went a bit haywire on social media, the audience’s reactions were mixed, with more than a handful of cuts to bewildered faces. Nevertheless, the performance ended with a standing applause, which may have provided some respite to Eminem.
9. John Travolta butchers Idina Menzel’s name (2014)
While introducing Idina Menzel’s performance of Frozen’s Let It Go, John Travolta confidently referred to her as Adele Dazeem. This rather bizarre mispronunciation instantly went viral, sparking countless memes and parodies.
Menzel soon got her revenge the following year by introducing Travolta as Glom Gazingo, though his over-affectionate face-touching during the bit made things awkward all over again.
Menzel held no hard feelings toward Travolta after the mishap. In fact, she was glad it happened. “It ended up being one of the best things that happened for my career,” she said, recalling how the slip-up piqued people’s curiosity.
Despite her initial frustration, she quickly refocused, saying “Get your s— together, you know? You gotta get ready to sing this note.”
Travolta would later joke, “What would Idina Menzel say? She’d say, Let it go!” It seems the two are now on good terms, with Menzel even tweeting before her 2020 performance, “Who is brave enough to introduce me?”
8. Trey Parker and Matt Stone are tripping at the Oscars (2000)
The creators of South Park have never been ones to play by the rules, and their Oscars appearance in 2000 was no exception. Back in the late ’90s, though, South Park’s future was far from guaranteed. Their 1999 film, Bigger, Longer & Uncut would, however, earn them an Oscar nomination.
Nominated for Best Original Song for Blame Canada, Trey Parker, and Matt Stone showed up on the red carpet wearing replicas of Gwyneth Paltrow’s pink gown and Jennifer Lopez’s green Versace dress from the previous year.
Later, they would admit that they were tripping on acid at the ceremony. The duo maintained their composure during interviews and had made a deal earlier that either of the two wouldn’t acknowledge their dresses to anyone else. They were, of course, too high to care – until the trip wore off midway through the painfully dull event.
7. Angelina Jolie and a moment of sibling love (2000)
Few moments have sparked as much attention as Angelina Jolie’s acceptance speech – and the subsequent kiss at the 2000 Oscars. Winning the Academy for Girl, Interrupted, Jolie took to the stage and gave a tribute to her brother, James Haven, who accompanied her.
“I am in shock and very much in love with my brother,” Jolie said during her speech. She later shared, “He just held me and said he loved me, and I know he’s very happy for me.”
The buzz only grew after the siblings shared a kiss on the lips while posing for photos, leading to widespread speculation. Months later, Jolie explained it was simply “sisterly love,” adding, “My parents really loved that moment, and that’s what will always matter.”
This gesture was, nevertheless, widely scrutinized, with many finding it inappropriate. Jolie and Haven later clarified that the moment was misinterpreted, but the incident remains a big talking point whenever cringe-worthy Oscars moments are discussed.
6. Jennifer Lawrence’s Famous Falls (2013 & 2014)
Someone tripping, the falling kind, is by no means funny. But for it to happen in two consecutive years – yeah, that won’t help on the embarrassment charts. At the 2013 Oscars, Jennifer Lawrence tripped on her voluminous Dior gown on her way to collect the Best Actress award for Silver Linings Playbook, hitting the floor like a swatted fly.
Rising with a grin, she joked, “You guys are just standing up because you feel bad that I fell”.
The next year, she fell again. This time on the red carpet. If it did anything at all, it made Lawrence all the more relatable.
Suddenly, celebs were photobombing red carpets, shrieking during Ice Bucket Challenges, and sharing “messy” Instagram dumps. Some of it’s try-hard, but seeing stars fumble makes us feel like stardom isn’t so out of reach.
5. Adrien Brody’s unconsented kiss (2003)
Winning Best Actor for The Pianist was a career highlight for Adrien Brody, but his acceptance moment became infamous for something more questionable. In a move that was equally shocking and appalling, Brody grabbed presenter Halle Berry and planted a long, unsolicited kiss on her lips as he walked down the stage to collect his award.
The audience initially laughed, but Berry’s shocked expression said it all. Years later, Berry confirmed the kiss was not consensual and described her thoughts at that moment, saying “What the f*** is happening?” She would also add that “the feeling of being out of your body” overcame her, and she “just f—ing went with it.”
4. David Niven’s Streaker Moment (1974)
The Oscars have had their share of odd moments, clearly, but none quite like the streaker at the 1974 ceremony. As David Niven introduced Elizabeth Taylor, a man wearing nothing but a mustache dashed across the stage, flashing a peace sign before vanishing off-camera.
Niven, remarkably composed, said, “Isn’t it fascinating to think that probably the only laugh that man will ever get in his life is by stripping off and showing his shortcomings?” The audience roared, and the show carried on.
The streaker, Robert Opel, wasn’t a random troublemaker. A queer activist and photographer, Opel used streaking as protest art, even disrupting city council meetings. Rumors persist that producer Jack Haley Jr. staged the stunt, given Niven’s ready one-liner and Opel’s backstage press interview.
Opel’s story, however, ended tragically in 1979 when he was murdered in his San Francisco art gallery.
3. Rob Lowe and Snow White’s Duet (1989)
The 1989 Oscars are widely remembered as one of the most embarrassing in the ceremony’s history, thanks to an opening number. Producer Allan Carr, trying to revive his career, scrapped the idea of having a host and started the night with a strange 11-minute performance instead.
It began with Eileen Bowman, an unknown actress dressed as Snow White, singing awkwardly while greeting uncomfortable A-list celebrities in the audience. Things went from just strange to awkward when Rob Lowe joined her on stage for a parody duet of “Proud Mary.”
Lowe sang off-key, belting lyrics like, “Used to work a lot for Walt Disney / Starring in cartoons every night and day,” with dancers dancing around them.
The fallout was, well, massive. Disney sued for Snow White’s unauthorized use, 17 Hollywood biggies signed a letter calling the show “an embarrassment,” and both Carr and Bowman’s careers ended. To this day, it’s considered one of the Oscars’ lowest points
2. The La La Land/Moonlight Best Picture mix-up (2017)
The 89th Academy Awards will forever be remembered for the shocking Best Picture mix-up. In the night’s final and most anticipated moment, presenters Warren Beatty and Faye Dunaway mistakenly announced La La Land as the winner instead of Moonlight.
The confusion started when Beatty, handed the wrong envelope (the one for Best Actress, already awarded to Emma Stone), and hesitated before passing it to Dunaway, who declared La La Land the winner.
The La La Land team was mid-speech when producer Jordan Horowitz noticed the error. Grabbing the correct envelope, he announced, “There’s a mistake. Moonlight, you guys won Best Picture. This is not a joke,” holding up the card for proof.
The audience and press room couldn’t get their heads behind it, while host Jimmy Kimmel joked, “I blame Steve Harvey for this,” referencing the infamous Miss Universe mistake.
Despite the awkwardness, Moonlight director Barry Jenkins and his team were gracious, as were the La La Land crew. Jenkins called the moment “unprecedented” but praised all nominees.
The mix-up was pinned on accounting firm PricewaterhouseCoopers, who apologized for the envelope error. In the end, Moonlight made history as the first LGBT-focused film to win Best Picture, while La La Land still claimed six Oscars, including Best Director for Damian Chazelle.
1. Will Smith slaps Chris Rock (2022)
You knew this would take the mantle, there are no two ways about it. Nothing could have prepared viewers for what transpired at the 94th Academy Awards.
The incident occurred when Rock joked about Jada Pinkett Smith’s bald head, referencing G.I. Jane. While Will Smith initially laughed, Jada’s visible displeasure prompted him to walk on stage, strike Rock, and return to his seat, shouting, “Keep my wife’s name out of your (expletive) mouth!” Rock, stunned, responded, “Wow, dude. It was a G.I. Jane joke.”
The incident overshadowed the entire ceremony, including Smith’s own Best Actor win for King Richard, where he delivered a speech with tears in his eyes. Smith later apologized twice – once in a statement calling his actions “unacceptable and inexcusable,” and later in a video.
Despite reaching out, Rock was reportedly “not ready to talk.” The Academy banned Smith from events for 10 years, and he resigned shortly after the slap.
Rock also later addressed the incident in his Netflix special, joking, “It still hurts! I got Summertime ringing in my ears!” He joked about their size difference, noting, “Will played Muhammad Ali; I played Pookie in New Jack City.”
Dubbed “the slap heard around the world,” it remains one of the most shocking, if not the most, embarrassing moments in Oscars history.
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