The Most Embarrassing Award Show Moments That’ll Make You Cringe

Awards shows can be fun and exciting, and you are just never sure what will happen next. No wonder many people live for these unpredictable moments.

Of course, it’s fun to watch celebrities parading on the red carpet with the most glamorous and expensive outfits ever. However, it is equally important for most people to watch the drama that usually unfolds during these shows.

There is no denying that it can be pretty hilarious to watch wardrobe malfunctions, celebrity beef unfolding in real life, embarrassing falls, bizarre acceptance speeches, and other hilarious mistakes that happen to live on television. In recognition of this fact, here are 40 plus of the most unforgettable and embarrassing award show moments people have yet to forget about.

1. Kanye West’s Rude Interruption Of Taylor Swift – 2009 MTV Video Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

The awkward moment Kanye West created during the MTV Video Music Awards in 2009 is remembered as one of the most embarrassing moments in award shows history. As Taylor Swift was giving her acceptance speech during the awards ceremony, Kanye West jumped on the stage to make an announcement.

The rapper took the mic and tried to explain why Beyonce should have won the award instead:

“Imma let you finish, but Beyonce had one of the best videos of all time!”

The statement was an absolute embarrassment for Swift, and not even Beyonce looked flattered by the awkward endorsement: she looked quite mortified.

Of course, Taylor Swift has won several awards over the years, and nobody can say she didn’t deserve the prize, as Kanye implied. In fact, Kanye later apologized to her.

Taylor Swift has won herself hundreds of awards over her career.

2. John Travolta Calling Of Idina Menzel, “Adele Dazeem” – 2014 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Idina Menzel has an angelic voice that has won her plenty of fans around the world. During the 2014 Oscars, she performed the popular hit Let it Go from Frozen, but the performance came after John Travolta completely butchered her name.

To be fair, Travolta was giving the Wicked and Rent star quite an excellent introduction and even described her as “wickedly talented.” However, that was quickly forgotten after he referred to her as “Adele Dazeem.”

Idina was not going to take the humiliation of sitting down. The following year, she welcomed him to the 2015 Academy Awards as “Glom Bazinga.”

3. Jennifer Lawrence’s Stumble While Going To Collect Her Award – 2013 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Falling under any circumstances in front of a whole bunch of people is enough embarrassment. So, you can imagine how the Hunger Games star, Jennifer Lawrence, felt when she stumbled while walking up the steps to accept an Oscar for Silver Linings Playbook.

Fortunately, she saw the funny side to her minor incident and even thanked the audience for standing up when she fell.

Later, she admitted that a bit of communication problem might have led to the incident. Her stylist had told her to “kick, walk, kick, walk” when wearing the dress.

However, when she fell, she could not remember these words, and instead, the phrase “cakewalk” was stuck in her head. That was her downfall, literally.

4. Ricky Gervais Offering Hollywood Advice – 2020 Golden Globes

The Most Embarrassing Award Show Moments That'll Make You Cringe

Ricky Gervais has hosted the Golden Globes five times. However, in 2020, the British comedian took the opportunity to lecture Hollywood on several things.

He warned those who would win an award against using the opportunity to make political statements. Gervais then warned the winners that they were not in a position to “lecture the public about anything.”

The comedian kept on going and touched on many taboo subjects, including ISIS and Jeffrey Epstein. He even found an opportunity to promote After Life, his show.

5. Madonna’s Wardrobe Malfunction Caused Her Fall – 2015 BRIT Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

In the show business, regardless of how big you are, mishaps can happen. Madonna learned this the hard way when a problem with her wardrobe made her fall as she performed “Living For Love.”

Her cape was ripped off by one of her backup dancers, and she fell. Coincidentally (or hilariously, depending on how you see it), she was singing “I let down my guard” when this happened.

In all fairness, the experience seemed pretty painful, but being the pro that she is, Madonna did not let that stop the show. The singer composed herself and went on to complete her performance.

6. Beyonce’s Backtrack Issues When Performing With Sean Paul – 2003 MTV Europe Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Beyonce is quite the performer, and you can always bet she will give her best when on stage. However, in 2003, she had to face an embarrassing situation during an awards show.

At the time, she was performing Baby Boy alongside Sean Paul. Unfortunately for her, the track had problems and would not stop repeating, “Baby boy. You are so damn fine” over and over again.

Sean Paul kept doing his bit by rapping, but Beyonce walked offstage before she came back on the stage to perform all over again.

7. Taylor Swift Thought She Had Won An Emmy – 2014 Grammys

The Most Embarrassing Award Show Moments That'll Make You Cringe

Alicia Keys had hardly said the album’s name who had won Album of the Year when Taylor Swift thought she was the lucky winner. Her album, Red, was in the running, but Alicia Keys was speaking about Random Access Memories by Daft Punk.

Fortunately, she had won the award in 2010 for her album, Fearless and has so far won the award three times. At the moment, she has already won 11 Grammy’s.

8. Nicki Minaj Calling Out Miley Cyrus During Her Acceptance Speech – 2015 MTV Video Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Typically, artists are pretty thankful and joyous when they win an award, often reflected in their acceptance speeches.

Nonetheless, when Minaj bagged the Best Hip-Hop Video award, she took the opportunity to get back to Miley Cyrus, who had earlier said in an interview that Minaj was “not too kind.”

Minaj referred to Miley as a “b—h that had a lot to say about me the other day in the press.”

9. Michael Jackson Thinking He Won A Nonexistent Award – 2002 MTV Video Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Through his music, Michael Jackson helped define music history. However, he still made an embarrassment of himself after walking on stage to accept an award that was not even available.

Britney Spears was wishing the iconic artist a happy birthday and claimed that she saw him as the “artist of the millennium.” Jackson thought this was an award category, walked up on stage, and gave an acceptance speech.

In the speech, he mentioned that if someone had told him he would one day win the Artist of the Millennium award,’ he would never have believed it. Unfortunately, such an award does not exist, and the King of Pop only managed to make an embarrassment of himself.

10. Sofia Vergara’s Decision To Stand On A Pedestal – 2014 Emmy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

As far as beauty goes, Sofia Vergara is among the most attractive women in Hollywood. This is an opinion shared by many, including Bruce Rosenblum, the chairman of the Television Academy.

As he was giving a speech on the TV industry, Vergara was striking a pose on the pedestal. The final words of his speech seemed to have something to do with Vergara’s dramatic pose:

“What truly matters is that we never forget that our success is based on always giving the viewer something compelling to watch.”

Without a doubt, the Modern Family actress helped achieve this by climbing onto the pedestal and looking like a glamorous award.

11. Anne Hathaway’s Lack Of Chemistry With James Franco – 2011 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Anne Hathaway and James Franco hosted the Oscars in 2011. However, their chemistry was so bad that it made the awards show pretty awkward.

While Hathaway was bubbly, Franco remained so chilled throughout the night, and it was clear to everyone that the two couldn’t be more different if they tried.

Their hosting was full of awkward moments until James Franco made things orders of magnitude worse by trying to look like Marilyn Monroe in Gentlemen Prefer Blondes. Fortunately, it wasn’t a thoroughly disappointing night for Franco, who had a nomination for Best Actor for his role in 127 Hours.

12. Melody Showing Up Later To The Performance – 2006 American Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Pussycat Dolls are famous all around the world. However, their performance during the 2006 American Music Awards did not work out as planned after Melody showed up late.

Fortunately, the entire group was doing such a great job performing their hit Buttons that most people didn’t realize one of the group members was nowhere to be seen over most of the performance.

Melody made it to the stage with 40 seconds left, and as if that was not bad enough, she went on to sing over Nicole Scherzinger’s vocals. Her embarrassing behavior might be understandable, considering she later admitted that she felt “worthless” when in the group.

The fact that the group could put on a compelling show without her somehow supports this theory.

13. Jennifer Lopez Fell During A Performance – 2009 American Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

J-Lo is one of the best performers in the world, and she is also an incredible dancer. That means her shows are always unforgettable and riveting.

Unfortunately, one of her performances is remembered, not for her dancing and singing prowess, but because she ended up falling on the stage.

She was performing Louboutins when she decided to try a stunt with her backup dancers forming a staircase for her to climb upon. She was jumping off the last dancer when she messed up her landing and fell.

Luckily, the experienced singer quickly got up and continued with the excellent performance.

14. Angelina Jolie Kissing Her Brother James Haven – 2000 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

In 2000, Angelina Jolie won the Best Supporting Actress award for her role in Girl Interrupted. However, by the time the awards were over, that was not what people were talking about.

She shared a kiss with her brother that shocked everyone.

The two kissed on the lips right in front of the cameras, which was made more awkward because she had said she was in love with her brother while giving her acceptance speech.

Obviously, for pretty close siblings, such gestures of emotion might not be strange. However, this was the last thing people expected to happen between the two famous siblings.

15. Lil Mama’s Interruption Of Jay-Z And Alicia Key’s Performance – 2009 MTV Video Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

In a lot of ways, the 2009 MTV VMAs were incredible as far as embarrassing moments go. For starters, Kanye West famously interrupted Taylor Swift during her acceptance speech.

Then, as Jay-Z and Alicia Keys’ performed Empire State of Mind, Lil Mama decided to jump in uninvited during the performance. She then went on to pose with the two artists after the song came to an end.

Later, she apologized for the incident and explained that she did not intend to be disrespectful but was “feelin’ it, and it just happened.” All things considered, Lil Mama’s decision is a complement to Jay-Z and Alicia Keys for making such a great track.

16. Naked Man On Stage As Elizabeth Taylor Was Being Introduced – 1974 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Back in the 70s, security was not as tight as it is today, which might explain why a naked man would make it to the stage and cause an embarrassment that is remembered today.

David Niven, the co-host, was introducing Elizabeth Taylor when the incident happened. The man even managed to make a peace sign.

Fortunately, Niven and Taylor took the weird interruption in their stride with Taylor saying:

“That’s a pretty hard act to follow.”

The man turned out to be an artist, gay rights activist, and photographer. His stunt got him some attention.

17. Jacqueline Bisset’s Awkward Acceptance Speech – 2014 Golden Globes

The Most Embarrassing Award Show Moments That'll Make You Cringe

Actors are not always ready at the time they are told that they have won an award. After all, some of them get nominated dozens of times before they finally win an award.

Jacqueline had been nominated five times when she won the award for Best Supporting Actress in a TV Show, Miniseries, or TV Movie for her role in Dancing on the Edge.

What was unusual about her acceptance speech was the fact that she dropped an “S word.” After that, she said:

“Like my mother used to say, ‘Go to hell and don’t come back’.”

18. Katy Perry’s Fall – 2008 MTV Latin America Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Katy Perry’s I Kissed a Girl performance left many people surprised during the MTV Latin America Awards. As if that was not enough, she jumped on a big pink cake, slipped on the icing, and fell.

Even after trying to get up with her guitarist’s help, she ended up slipping three more times before she gave up and crawled away.

19. Nicole Kidman’s Unusual Clapping – 2017 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

People have been watching Nicole Kidman for a while, and it’s all thanks to her unique clapping technique. Ever since people realized that her clapping looked seal-like, memes popped up everywhere making fun of her.

She even addressed the issue in the media, where she admitted that she had resulted to the clapping technique to avoid causing damage to her expensive rings.

Apparently, she was divided on whether to clap or not and wondered how it would seem if she didn’t. The compromise was doing the strange seal-like clap.

20. The Man Behind Neil Patrick Harris – 2013 Emmy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

On two occasions, Neil Patrick Harris has hosted the Emmys. However, the second time he did it is remembered by many because a man appeared behind him.

The guy seemed oblivious to what was happening, which made his presence even more awkward. Later, it was confirmed that the man was Paul Greenberg, one of the show’s writers.

21. Miguel Falling On A Fan – 2013 Billboard Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Miguel was perfect as he was performing Adorn until he made the regrettable decision to jump from one part of the stage to another. The move failed spectacularly, and the performer ended up falling on fans.

From the look of things, the fall must have been painful. Fortunately, everyone seemed to be okay afterward.

He took it quite well based on what he said when he was later interviewed about it. After the performance, he introduced his new friend Khyati and claimed that they were both fine, although they did not meet under perfect circumstances.

22. Joe Jonas Fall, Which Hurt His Hand – 2007 American Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

During their performance of SOS during the 2007 American Music Awards, the Jonas Brothers made quite the dramatic entrance. People were quite impressed by their ingenuity when three panels of glass shattered in front of them.

The setup was quite breathtaking. Unfortunately, Joe tripped over the panel and sliced his hand on the glass lying on the ground.

Luckily, all Joe got was a small cut, which did not keep him from putting on a fantastic performance. When he finally got backstage, he said it was “just a little blood.”

23. Sam Smith Messing Up An Ian McKellen Quote – 2016 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

When Sam Smith won an Oscar for Writing on the Wall, it was a big deal. This was his first award, and he thought he would use the moment to show appreciation to the LGBT community by quoting Sir Ian McKellen’s words.

He claimed: “No openly gay man had won an Oscar.”

However, McKellen had claimed that no gay man had won an Oscar for the Best Performance by an Actor in a Leading Role. Fortunately, McKellen came to the singer’s defense and went on to congratulate him on Twitter.

24. Seth McFarlane Offended The Audience With A Sexist Joke – 2013 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

When Seth McFarlane, the creator of Family Guy, hosted the Academy Awards in 2013, many people were offended by his intro. He used the opening number, We Saw Your Boobs, which had shots of Charlize Theron and Naomi Watts looking mortified.

The performance was considered offensive by many people. However, despite looking like a bad host, the ratings shot up, and he was invited to host it again the following year.

25. Chrissy Teigen’s Strange Crying Face – 2015 Golden Globes

The Most Embarrassing Award Show Moments That'll Make You Cringe

Chrissy Teigen turned into a dream come true for many meme makers for her crying face, which she made as her husband, John Legend, would receive an award for Best Original Song.

The face soon went viral, and she later wrote on Twitter that the reason for the strange look was that she had not practiced her crying face properly.

26. “La La Land” Mistakenly Declared Winner Instead Of “Moonlight” – 2017 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Anyone can make a mistake, even during a carefully planned event like a world-famous awards show. For instance, during the 2017 Academy Awards, La La Land was announced as the winner for Best Picture, and moonlight had won the title.

The problem was that Faye Dunaway and Warren Beatty, Bonny and Clyde actors, were given the wrong envelope as they presented the award.

By the time the confusion was sorted out, La La Land had already made an acceptance speech. The presenters had gotten an envelope that said that Emma Stone had won the Best Actress Award for La La Land.

27. David Letterman’s Bad Joke – 1995 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Hosting an important awards show can be a huge undertaking, even for seasoned people like David Letterman. As the television show host hosted the 1995 Oscars, he made a joke that did not work out as expected.

Nobody got what Letterman was talking about when he said:

“I’ve been dying to do something all day and I think maybe we an take care of this. Oprah? Uma. Uma? Oprah. I feel much better. Have you kids met Keanu?”

28. Leonardo DiCaprio Making A Face At Lady Gaga – 2016 Golden Globes

The Most Embarrassing Award Show Moments That'll Make You Cringe

Leonardo DiCaprio managed to turn into a popular GIF when he seemed to cringe as Lady Gaga walked past him to accept an award for Best Actress in a Mini-Series or Motion Picture for TV for her role in American Horror Story: Hotel.

Later, the popular actor claimed that he made a face because he had no idea what was passing.

29. Faith Hill’s Disappointment With Carrie Underwood’s Win – 2006 Country Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

In 2006, Faith Hill and Carrie Underwood both got nominations for Female Vocalist of the Year at the Country Music Awards. However, after Underwood won, it became quite apparent that Faith Hill did not expect that to happen.

Before the winner was announced, Faith Hill was smiling, but after Underwood was announced as the winner, her smile quickly faded, and she shouted, “WHAT.”

To fans, it seemed like the loss to Underwood upset her. However, she later clarified that she would never be disrespectful to a fellow musician and claimed that Underwood was a talented musician who deserved to win the Female Vocalist of the Year award.

30. Rob Lowe’s Decision To Sing With Snow White – 1989 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Rob Lowe is a great actor, and nobody can deny that. However, he shocked everyone when he decided to sing alongside an actress dressed up as Snow White during his opening performance.

Although his performance was entertaining, it got a lot of criticism. It turned out that Allan Carr planned the performance, and Disney was not too happy with the Snow White being used without their authorization.

31. Nicki Minaj Wardrobe Malfunction During Her Performance – 2014 MTV Music Video Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Nothing would get in the way of Nicki Minaj completing her performance in 2014 when she suffered a wardrobe malfunction when performing Bang Bang with Ariana Grande and Jessie J.

Her dress could not be zipped up properly, and she had to hold it with her hands as she rapped. It also became clear that she did not have any underwear on.

Apparently, she made a last-minute decision to wear a black dress to match Ariana and Jessie J., a decision that did not work out in her favor during her performance.

32. Britney Spears’ Strange Performance – 2007 MTV Video Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Britney Spears is quite a performer, and she has shocked her fans with her performances in the past. For instance, she once performed with a python on her shoulders.

In 2007, however, she was doing Gimme More when her performance stood out for being a little underwhelming. The singer was distracted and dancing off rhythm.

Therefore, what was supposed to be a huge comeback for her turned into an even bigger source of concern for her fans, with critics predicting that her career had finally ended. Fortunately for her fans, the critics were wrong about her as she put on quite a show during the VMA awards in 2016.

33. Lady Gaga And The Meat Dress – 2010 MTV Video Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

When it comes to dressing, you can never predict what Lady Gaga will put on next. Sometimes, she wears something unique and amazing, but her fashion choices can be quite bizarre at other times.

For instance, many remember her for showing up to the 2010 MTV Video Music Awards with a meat dress. She received an award for Album of the Year for The Fame while wearing the shocking outfit.

To this day, people still remember the dress, which was later dried out and put in the Rock & Roll Hall of Fame.

34. Nicole Kidman Ignoring Rami Malek – 2019 Golden Globes

The Most Embarrassing Award Show Moments That'll Make You Cringe

Typically, the person presenting an award to the winner greets them with a big hug. However, something else happened when giving Rami Malek an award for Best Drama for his role in Bohemian Rhapsody.

The actress turned her back on the actor, and he even tried getting her attention by touching her back.

However, it turns out that this incident had nothing to do with the two hating each other. She admitted that she did not feel him touching her back and that they apparently emailed each other about it later and had a good laugh.

35. Natalie Portman Calls Out Best Director Nominees – 2018 Golden Globes

The Most Embarrassing Award Show Moments That'll Make You Cringe

Many people have an issue with the fact that awards ceremonies often offer all-male or all-white nominees. Natalie Portman did not hesitate to point out that the nominees for Best Director were all men when she presented an award for Best Director during the Golden Globes.

Before the montage showing the films that had produced nominees for Best Director, she said, “Here are the all-male nominees.” As her co-presenter, Howard laughed, Portman looked serious.

36. Miley Cyrus’ Twerk – 2013 MTV Video Music Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Back in the day, Miley Cyrus was a famous Disney star, but she has changed in a big way since then. In 2013, she released Bangerz, which helped her ditch the juvenile Hannah Montana image.

She also got on stage with Robin Thicke as he performed Blurred Lines. However, people thought she went too far when she twerked with her tongue sticking out.

Many people complained to the FCC about the performance, which has never been forgotten to this day.

37. Björk Laid An Egg – 2001 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Björk will never be forgotten for wearing a swan dress on the red carpet during the 2001 Academy Awards. This was one of the most unforgettable red carpet looks ever.

The singer pushed things further by laying an egg while she posed. Apparently, she brought with her half a dozen eggs that she laid all around the red carpet.

The eggs had been hidden inside her dress to help complete her iconic look. She would lay the eggs when the moment was right, creating one of the most dramatic Academy Awards moments ever.

38. Elinor Burkett Rushing To The Stage – 2009 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Kanye West is not the only celebrity with a problem staying put when it’s someone else’s chance to give an acceptance speech. In 2009, Elinor Burkett interrupted an acceptance speech for Best Documentary, Music by Prudence, presented by Roger Ross Williams.

She had been part of the production crew, but the film’s producers had gotten rid of her.

Despite the interruption, during which Burkett gave her speech, Williams went on to get everyone’s attention and do his part in appreciating the win.

39. Gwyneth Paltrow’s Long Acceptance Speech – 1998 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

When Gwyneth Paltrow won Best Actress for Shakespeare in Love, she gave one of the longest acceptance speeches ever. She thanked a lot of people, including her family and her agent.

Later, Paltrow admitted that even she didn’t watch the speech. People think it would be truly incredible if it turns out that she forgot to thank anyone during the winding acceptance speech.

40. Kirstie Alley’s Unacceptable Joke – 1991 Emmy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

Macaulay Culkin was incredible as he presented the Best Actress award in a Comedy Series to Kirstie Alley for her role in Cheers. However, when the actress took to the stage, she made a crude joke and thanked her husband, Parker Stevenson.

She described him as “the man who has given me the big one for the last eight years.”

41. Brad Pitt, Angelina Jolie And Jennifer Anniston Meet – 2009 Academy Awards

The Most Embarrassing Award Show Moments That'll Make You Cringe

When Brad Pitt’s and Jennifer Aniston’s marriage came to an end in 2005, everyone was shocked. Things between the two were still awkward even after the two met during the Oscars four years later.

Aniston was presenting, and Pitt and Jolie were sitting in the front row together. The couple smiled as Aniston presented Best Short Film and even clapped as she walked to join her boyfriend, John Mayer.

So, which of these do you think is the strangest awards show moment ever?