15 Most Embarrassing Award Show Moments That’ll Make You Cringe All Over Again

You know what they say, folks - award shows are like a box of chocolates, you never know what you're gonna get! Sure, we love to ooh and ahh over the fancy red carpet outfits, but let's be real - the true gem of any award show is the drama! We're talking about everything from tripping on stage to fashion faux pas. Whether it's a full-blown feud or just a petty argument, you better believe we're here for it.
And do we have a treat for you! Not one, not two, but FIFTEEN of the most cringe-worthy award show moments that are still burned into our brains. So sit back, and get ready to relive some of the most memorable and embarrassing moments in award show history. Just don't say we didn't warn you - these moments are so cringe-worthy, you might just want to watch through your fingers. Are you ready? Let's dive in!
And the cringe award goes to...

#1 Will Smith Slapped Chris Rock – 2022 Oscars

First up, we've got the infamous Will Smith and Chris Rock slap-fest at the 2022 Oscars. It was like a scene out of a movie, with Smith storming the stage and smacking Rock across the face after a joke about Jada Pinkett Smith's hair loss. And if that wasn't wild enough, Smith went on to win an Oscar for Best Actor later that night.

Source: Screenshot from 2022 Oscars

But the drama didn't stop there - the whole incident sparked a heated debate over who was in the wrong, and let's not forget the flood of memes that hit the internet afterwards.

#2 Kanye West and Taylor Swift: “Imma Let You Finish” – 2009 MTV Video Music Awards

The ultimate cringe-fest of all award show cringe-fests, we're talking about the infamous Kanye West and Taylor Swift moment at the 2009 MTV Video Music Awards. As Swift was giving her acceptance speech, Kanye West had the nerve to jump on stage and grab the microphone out of her hands, just to declare that Beyoncé deserved to win instead.

Source: Getty Images

"Imma let you finish, but Beyoncé had one of the best videos of all time!", he declared. Even Beyoncé looked like she wanted to crawl under a rock. But fear not, Swifties, for our girl Taylor went on to win countless awards in the years to come. And Kanye? Well, let's just say he eventually realized the error of his ways and issued an apology. Better late than never, right?

#3 Madonna Fell Down The Stairs – 2015 BRIT Awards

Oh, the horror of taking a tumble on stage - and poor Madonna had to experience it firsthand at the 2015 BRIT Awards. While singing "Living For Love", the Queen of Pop took a spill due to a wardrobe malfunction. One of her backup dancers accidentally ripped off her cape, causing her to lose her balance and fall down the stairs. Ouch!

Source: Getty Images

To add insult to injury, the fall happened right as she was singing the lyrics "I let down my guard". Talk about awkward timing. But true to form, Madonna dusted herself off and carried on like a boss, taking a moment to regain her composure before continuing with the performance.

#4 Michael Jackson Thought He Won “Artist Of The Millennium” – 2002 MTV Video Music Awards

At the 2002 MTV Video Music Awards, Michael Jackson was in for a surprise when Britney Spears wished him a happy birthday and called him the "artist of the millennium." MJ took it to heart and rushed to the stage to deliver an acceptance speech for an award that, unfortunately, did not exist.

Source: Getty Images

Oops! It just goes to show that even legends like MJ can fall for a good prank. At least he took it like a champ and gave us all a good laugh.

#5 Angelina Jolie Lip Kissed Her Brother – 2000 Academy Awards

Angelina Jolie made headlines at the 2000 Academy Awards not just for her Best Supporting Actress win, but for the kiss she shared with her brother James Haven. The siblings locked lips on the red carpet, and during her acceptance speech, Jolie declared, “I’m so in love with my brother right now, he just held me and said he loved me.”

Source: Mediapunch / Shutterstock

While it may be normal for close siblings to show affection, it was still a bit of a shock to see such an intimate moment on live television.

#6 Katy Perry Kept Falling – 2008 MTV Latin America Awards

Katy Perry's performance of "I Kissed a Girl" at the 2008 MTV Latin America Awards was a real show-stopper - but not for the reasons she intended. After jumping into a giant pink cake at the end of the performance, Perry found herself slipping and sliding all over the place, unable to get back on her feet.

Source: Screenshot from 2008 MTV Latin America Awards

Despite the best efforts of her guitarist to help her up, Perry fell not once, not twice, but four times before finally crawling offstage in defeat.

#7 Nicole Kidman’s Seal Clapping – 2017 Academy Awards

Nicole Kidman's seal-like clapping at the 2017 Academy Awards made her the talk of the town, but not for her acting skills. Memes of her unique clapping style flooded the internet, with many pointing out the resemblance to a seal's flippers.

Source: Screenshot from 2017 Academy Awards

Kidman later explained that she was trying to avoid damaging her expensive rings. But let's face it, once you've been dubbed the "Seal Clapper," there's no going back.

#8 John Travolta Mispronounced Idina Menzel's Name – 2014 Oscars

John Travolta's mispronunciation of Idina Menzel's name at the 2014 Oscars became one of the most talked-about moments of the show. He introduced her as "Adele Dazeem," which quickly went viral on social media.

Source: Kevin Winter / Getty Images

Despite the mishap, Menzel delivered a stunning performance of "Let It Go" from the hit Disney film Frozen. One year later, she welcomed John to the 2015 Academy Awards, calling him “Glom Bazinga”. What a petty but sweet revenge!

#9 Chrissy Teigen’s funny Crying Face – 2015 Golden Globes

Chrissy Teigen's funny crying face at the 2015 Golden Globes is definitely a memorable awards show moment that has since become a popular meme on social media.

Source: Screenshot from 2015 Golden Globes

Her candid and relatable expression has been used in a variety of contexts and continues to be shared and enjoyed by people around the world.

#10 Lady Gaga’s Infamous Meat Dress – 2010 MTV Video Music Awards

Who can forget the whole Meat Dress controvery, right? When she won Album of the Year at the 2010 MTV Video Music Awards, she shocked the world by accepting the award in a gown made entirely of meat.

Source: Kevin Winter / Getty Images

The dress had mixed reviews, but it's safe to say it's now a part of pop culture history. And get this - it was even dried out and displayed at the Rock & Roll Hall of Fame! Now, that's what we call a rare piece of fashion.

#11 Miley Cyrus’ Twerking On Robin Thicke – 2013 MTV Video Music Awards

Let's take a trip down memory lane to the 2013 MTV Video Music Awards, where Miley was on a mission to prove that Hannah Montana was long gone and replaced by a wild child.

Source: Jemal Countess / FilmMagic

As she took the stage with Robin Thicke to perform "Blurred Lines", Miley rocked a flesh-toned latex bra and matching bottoms, twerking like there was no tomorrow and waving a foam finger around. The performance definitely raised some eyebrows and even landed the FCC with a few complaints, but hey, that's just Miley being Miley, right?

#12 Brad Pitt, Angelina Jolie, and Jennifer Aniston – 2009 Academy Awards

Remember when Brad Pitt and Jennifer Aniston were the ultimate power couple before they split in 2005 and he moved on to his "Mr. & Mrs. Smith" co-star, Angelina Jolie?

Source: Getty Images

Well, four years after their separation, things were still pretty tense between Brad and Jen at the Oscars. Pitt and Jolie were seated in the front row while Aniston was up on stage presenting. As Aniston was giving her speech, Pitt and Jolie had these huge grins on their faces and gave her a round of applause when she was done. Meanwhile, Aniston went to join her then-boyfriend John Mayer.

#13 Nicki Minaj’s Holding Her Dress On Stage – 2014 MTV Music Video Awards

During her set of "Bang Bang" with Ariana Grande and Jessie J, Minaj had to do a quick wardrobe change and decided to go with a black dress to match her fellow singers.

Source: Rex / Getty Images

But as she tried to zip up the dress, disaster struck - the zipper just wouldn't budge! With the music already playing, Minaj had no choice but to hit the stage with her dress wide open, holding it up with her hands while she rapped her heart out. And if that wasn't embarrassing enough, rumor has it that she wasn't even wearing any underwear!

#14 Leonardo DiCaprio Made A Weird Face At Lady Gaga – 2016 Golden Globes

It was the awkward moment heard 'round the world at the 2016 Golden Globes - as Lady Gaga made her way to accept her award, she had to squeeze by Leonardo DiCaprio, and the actor's face contorted into a strange expression as she passed him.

Source: Screenshot from 2016 Golden Globes

The moment quickly became a viral GIF, but DiCaprio was quick to set the record straight - he wasn't cringing at Lady Gaga, he just wasn't sure what was passing him by!

#15 “La La Land” and “Moonlight” Best Picture Mix-Up – 2017 Academy Awards

This was the biggest mistake in Oscar history - at the 2017 Academy Awards, when presenters Faye Dunaway and Warren Beatty were given the wrong envelope. When they announced the winner for Best Picture, they read the name "La La Land," but it was actually "Moonlight" that had won.

Source: Screenshot from 2017 Academy Awards

The mistake was eventually cleared up, but not before the La La Land team had already taken the stage and started their acceptance speeches.