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A ranking of the most cringe-worthy Oscars moments.

The Oscars are Hollywood’s biggest night, where all the biggest stars gather in their fancy dresses and suits to celebrate each other.

But besides the glamour, the absolute best part of any Oscars ceremony is that each year there is guaranteed to be an awkward, cringe-worthy moment (or ten).

From badly timed falls, teleprompter fails and literally announcing the wrong film for the night’s most important award… Never does an Oscars ceremony go smoothly. And we live for those moments where it all gets a little… uncomfortable.

The best moments from the 2019 Oscars. Post continues below video.


Video via Mamamia

In preparation for the 2024 fails, we’ve collated and ranked our favourites from past years on a scale of ‘Yikes’ to ‘We’re just going to curl up in bed and rock back and forth, thanks’:

11. Natalie Portman’s burn.

The Oscars has faced lots of criticism for its lack of diversity over the years, and in 2018 Natalie Portman made a very pointed jab at the fact no woman had been nominated for Best Director.

“Here are the all male nominees,” she said before the lineup was shown.

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10. JLaw trips. And trips again.

JLaw is definitely the most clumsy person in Hollywood and we love it.

In 2013, she nearly face-planted as she climbed the stairs to accept her award for Best Actress for Silver Linings Playbook.

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At the following year's awards she tripped again on the red carpet and nearly took a friend down with her.

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9. Bjork laying an egg.

In 2001, Icelandic singer Bjork turned up to the Oscars red carpet in what is perhaps now the most infamous red carpet outfit ever.

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Images: Getty.
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But the swan dress wasn't enough on its own. No. In order to truly cement herself in Oscars history, Bjork then stopped mid-carpet to... lay an egg.

8. John Travolta 'kisses' ScarJo.

John Travolta was really living his best, cringe-inducing life circa 2014-2015.

In 2015, Travolta was photographed embracing and kissing Scarlett Johansson on the cheek, while ScarJo looked slightly uncomfortable. She later told the Associated Press the encounter was "very sweet and totally welcome" but even so... these photos live on.

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7. 'Oprah-Uma'.

Watching a comedian's joke bomb on the stage of Hollywood's biggest night - in the year the Oscars hit a record number of TV viewers - and having said bombed joke involve OPRAH?

NOPE. So much NOPE.

In 1995, David Letterman opened the Academy Awards with a joke that no one quite... got.

Letterman introduced Oprah and Uma Thurman to each other, before randomly bringing up Keanu Reeves.

The confused faces of Oprah and Thurman are straight out of our nightmares.

oprah uma oscars
"What... is... happening..." Images: YouTube.
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6. When the Oscars remembered the death of the wrong Australian...

Australian costume designer Janet Patterson was included in the 2016 awards' 'In Memoriam' tribute, but the Academy included a photo of Aussie film producer Jan Chapman who is most definitely still alive.

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Image: ABC.

IMAGINE BEING JAN OR JANET'S FAMILY OR THE PERSON WHO PUT TOGETHER THIS SLIDE.

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5. Just... everything about Anne Hathaway and James Franco.

Look, there's a lot Anne Hathaway can do. Successfully hosting the Oscars just happens to not be one of them.

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In 2011, Hathaway and James Franco co-hosted the big event and it was, objectively, the absolute worst.

Firstly, they were completely mismatched as co-hosts, they had zero chemistry, and Franco seemed to find the whole event mildly amusing.

In fact, it was downright cringe-worthy with Hathaway acting like an over-eager theatre kid and Franco looking like he wanted to be, well, literally anywhere else.

Hathaway can laugh about it now... but her opening like: "Oh my gosh, you're all real" will never not make us a bit queasy.

4. Seth Macfarlane's problematic opening.

In 2013, Seth Macfarlane opened the Academy Awards with a sexist original song called 'We Saw Your Boobs', name-dropping all the women who had gone topless in films.

From Meryl Streep to Naomi Watts and Nicole Kidman to Kate Winslet... He mentioned anyone who was anyone and it was just straight up uncomfortable.

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Unimpressed reactions from Naomi Watts and Charlize Theron were pre-recorded, so they were definitely in on the whole thing... but it's still weird, okay. The song fueled opinion pieces and think pieces for days, and we can't help but feel it would never have made the stage in 2024.

3. The birth of Adele Dazeem.

Who could forget when John Travolta introduced Frozen's Idina Menzel as Adele Dazeem at the 2014 Oscars? It quickly found itself in Oscar’s history books as one of the most awkward faux pas of all time.

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Then, the Academy knew how much we loved it and decided to recreate the moment by having John and Idina present together the following year. This involved a lot of face touching by Travolta. It was gloriously weird, and he very wisely let her pronounce her own name.

2. Angelina Jolie and her brother.

Ah, 2000. The year we realised Y2K was not a thing and Angelina Jolie declared her love for her brother James Haven and kissed him on the lips at the Vanity Fair after party which they attended with their dad, Jon Voight.

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"I'm so in love with my brother right now," Jolie said during her acceptance speech for Best Supporting Actress.

The after party kiss fuelled an endless supply of headlines and as parodied on Saturday Night Live, basically the only 2000 equivalent of a viral meme.

1. La La Land... oh wait.

In 2017, Faye Dunaway and Warren Beatty were tasked with presenting the biggest award of the night, Best Picture.

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As he opened the envelope and prepared to announce the winner, Beatty looked MIGHTY confused. He paused, looked around and then spectacularly threw Dunaway under the bus by having her announce La La Land as the winner.

The film's team celebrated and headed up on stage. They began to give their speeches, as Oscars team members started to run on stage. A man with a headpiece grabbed the envelope and took a look... while everyone on stage, except the poor men making heartfelt acceptance speeches, looked highly confused and concerned about the commotion.

Then... Oh, shit. It took producers nearly three minutes and three full speeches to announce the mistake, with La La Land producer Jordan Horowitz being the one to say it out loud:

"There's a mistake. 'Moonlight,' you guys won best picture... This is not a joke," he said.

The Moonlight team, audience and precisely all of us were shook to our core, then the Moonlight cast and crew dashed up on stage to collect their award.

It turned out Beatty had been given the wrong envelope, receiving a duplicate of the Actress in a leading role award that had earlier been won by Emma Stone.

You can watch this 100 times, and it'll still make you want to curl up in a dark corner in the fetal position.

Here's hoping for some more awkward moments - but maybe not this awkward - during 2024's show.

Feature images: Getty and YouTube.

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