HomeTrending30 Awards Show Moments That Will Make You Cringe for Days

30 Awards Show Moments That Will Make You Cringe for Days

Sure, awards shows are full of life-changing surprises and dazzling performances. But that’s not why you tune in. No, you’re looking for that uber-fail – the mix-ups, the gaffes, the faceplants. Whether they made you laugh or they gave you second-hand embarrassment, here are 30 of the all-time most awkward award show moments!

Leonardo DiCaprio Makes a Face at Lady Gaga (2016 Golden Globes)

When the American Horror Story star made her way to the stage to accept her Globe, she brushed by Leonardo DiCaprio, who flinched and seemed to give a bit of side-eye. “I just didn’t know what was passing me, that’s all!” DiCaprio told Entertainment Tonight.

There’s a Best Picture Mix-up (2017 Oscars)

In what became known as #Envelopegate, presenters Warren Beatty and Faye Dunaway were given the wrong envelope and mistakenly announced La La Land as the best picture winner. As it turned out, they’d been given another copy of the envelope declaring La La Land’s Emma Stone the best actress winner, which had already been announced. After what felt like an eternity, the La La Land acceptance speech was cut short and Moonlight was declared the true champion.

John Travolta Introduces Idina Menzel as “Adele Dazeem” (2014 Oscars)

Tasked with introducing Idina Menzel for her performance of “Let it Go” from Frozen, Travolta flubbed the singer’s name in the most bonkers way possible, welcoming “the wickedly talented, one and only Adele Dazeem.” Interestingly enough, the blunder significantly raised awareness of Menzel. “It’s definitely one of those welcome happy mistakes that changed my life,” Menzel told the New York Post.

David Letterman Makes a Bad Oprah Joke (1995 Oscars)

Letterman’s Oscar hosting stint will forever be remembered for a cringe-worthy joke he delivered right at the top of the show. “I’ve been dying to do something all day and I think maybe we can take care of this,” he said before locating Oprah Winfrey and Uma Thurman in their seats, so as to introduce them. “Oprah? Uma. Uma? Oprah. I feel much better. Have you kids met Keanu?” The audience laughed, but clearly out of politeness.

When Zac Efron Dropped a Condom On The Red Carpet For a Children’s Film

Zac Efron, the ultimate heartthrob, has embarrassing moments just like everyone else! During the premier of a kids movie, The Lorax, he dropped a condom from his pocket onto the red carpet. When speaking of the incident he said, “I never really had a pocket-checking policy before going on the red carpet before, but now we’ve fully instated one.” Yikes!

When Shia LeBeouf Did This

After storming out of a press conference for Nymphomaniac, LeBeouf announced he was going to withdraw from public life entirely. While heading to a Berlin screening of the film, he proceeded to cut eyeholes into a paper bag with the words, “I’m not famous anymore” in big black letters on it before placing it on his head while wearing a dapper tuxedo.

The Most Famous Forms Of Canadian Tuxedos

In 2001, Britney Spears and Justin Timberlake were the hottest and most gossiped about couple in Hollywood. For a while, they were a perfect match, just like these matching denim outfits they wore on the red carpet.

When Lady Gaga Did Anything Ever

Lady Gaga is the embodiment of the word “mystery”. Whether she’s wearing a dress of raw meat, or being shuffled onto the Red Carpet in a giant egg all night. Nobody has ever been more shocking and more surprising than Lady Gaga with her antics.

When A Streaker Ran Across the Stage at The Oscars

Nobody could have expected the surprise at the 1974 Academy Awards as host, David Nivens went to the mic to announce Elizabeth Taylor as the presenter for Best Picture. As he was speaking about how entertainment is a salve for the insanity of the world, a young man ran across the stage, completely naked and flashed the peace sign. The audience cheered and the band began playing a funny tune to deal with the awkwardness.

Natalie Portman’s Awkward Acceptance Speech

We could blame this on her pregnancy brain at the time, but Portman made us all hide our heads in embarrassment when she accepted the Golden Globe for Black Swan in 2011. Thank you to Benjamin, who is helping me to continue this creation of creating more life,” she said of her partner. “Benjamin choreographed the film and also you might remember him in the movie as the guy when they ask, ‘Would you sleep with that girl?’ and he’s like, ‘No.’ He’s the best actor. It’s not true. He totally wants to sleep with me,” she said, commencing the most awkward laugh in Globes history.

When Marlon Brando Declined His Oscar

In 1973, Marlon Brando won the Academy Award for Best Actor in 1973. However, instead of accepting the award, he sent Native American activist Sacheen Littlefeather to decline the award and protest Hollywood’s treatment of Native Americans.

Michael Jackson and Lisa Marie Presley’s Awkward Kiss

When Newlyweds Michael Jackson and Lisa Marie Presley kicked off the 1994 VMA’s, it was in a very awkward fashion. The King of Pop was attempting to silence rumors about his eyebrow-raising marriage to the Princess of Rock n’ Roll by saying “nobody thought this would last” and then pulled her into a suffocating and awkward kiss. Everyone felt uncomfortable. Also, it didn’t last, they divorced in 1996.

Then, When Michael Jackson Accepted an Award That Didn’t Exist

In 2002, the VMA’s fell on Michael Jackson’s 44th birthday and so MTV had Britney Spears say some words before presenting him with a trophy as a present. At one point during her introduction, she said she considered him to be “the artist of the millennium.” He then came out and accepted the award for “Artist of the Millennium”.

When Kanye Interrupted Taylor

We know that you saw this coming! There isn’t really anything to say about it that hasn’t already been said. At the 2009 VMA’s, when it was announced that Taylor Swift had won Best Video, Kanye quickly jumped up on stage during her acceptance speech to clarify that it was in fact, Beyonce who had one of the best videos of all time.

Jennifer Lawrence Falls (2013 Oscars)

As Lawrence moved up the steps to accept her Academy Award for Silver Linings Playbook, she tripped and fell to her hands in her glamorous Dior gown. “I was at the Oscars, waiting to hear if my name was called, and I kept thinking, Cakewalk, cakewalk, cakewalk. I thought, Why is ‘cakewalk’ stuck in my head?” she later told W magazine. “And then, as I started to walk up the stairs and the fabric from my dress tucked under my feet, I realized my stylist had told me, ‘Kick, walk, kick, walk.’ You are supposed to kick the dress out while you walk, and I totally forgot because I was thinking about cake! And that’s why I fell.”

Nicole Kidman Claps Like a Seal (2017 Oscars)

Oscar viewers were quick to notice that Kidman, applauding in the audience, seemed to be doing a movement closer to that of a seal than a human. Kidman soon after revealed it was so as not to damage the expensive rings she was wearing. “It was really awkward!” she told an Australian radio show. “I was like gosh, I want to clap, I don’t want to not be clapping, which would be worse, right? ‘Why isn’t Nicole clapping?’”

Rob Lowe Sings With Snow White (1989 Oscars)

In a performance that truly must be seen to be believed, a woman inexplicably in character as Snow White began by chirping uncomfortably to stars in the audience. Its awkwardness eventually peaked in a bizarre parody of “Proud Mary” with Rob Lowe. In its review, the New York Times declared that the opening “deserves a permanent place in the annals of Oscar embarrassments.”

Madonna Gets Yanked Down Some Stairs (2015 BRITs)

A dramatic wardrobe malfunction got the best of Madge during a performance of “Living for Love.” A backup dancer was supposed to pull off her Armani cloak, but Madonna was unable to untie it in time, which led to the pop queen being yanked backwards down a few stairs. She stopped singing for a moment, then powered through.

Sofia Vergara Rotates on a Pedestal (2014 Emmys)

Social media users called out the Emmys for a sexist bit that featured the Modern Family star striking poses on a rotating pedestal as the Academy’s chairman blabbered one of those boring speeches that Academy chairmen give. It could have been clever commentary on how Hollywood objectifies women, but instead the bit ended with the chairman creepily declaring, “What truly matters is that we never forget that our success is based on always giving the viewer something compelling to watch.”

Nicki Minaj Asks Miley Cyrus, “What’s good?” (2015 VMAs)

After Cyrus called Minaj “not too kind” in a New York Times interview, Minaj waited to clap back at the VMAs, which Cyrus was hosting. When the rapper took to the stage to accept the award for Best Hip-Hop video, she concluded by turning to Cyrus and saying, “Back to this bitch that had a lot to say about me the other day in the press. Miley, what’s good?” You could practically feel Cyrus quiver.

Britney Spears Delivers a Disastrous “Gimme More” Performance (2007 VMAs)

Spears’s much-hyped return to the VMAs stage was supposed to be the ultimate comeback moment, signaling that her tabloid troubles were behind her. Instead, she appeared so out of it during the obviously lip-synced performance of “Gimme More,” it seemed that trouble would be sticking around for a bit longer.

Beyoncé’s Has a Backing Track Malfunction (2003 EMAs)

It’s rare to see Queen Bey sweat, but sweat she did during this performance of her hit “Baby Boy” thanks to technical difficulties. As the song neared its conclusion, Bey’s backing vocal track went berserk, repeating “Baby boy, you are so damn fine” over and over. She eventually gave up and waved goodbye to the audience even as the track continued.

Sam Smith Incorrectly Congratulates Himself (2016 Oscars)

When accepting the award for best original song, Smith implied that he was the first openly gay man to win an Oscar. He said he was referring to a quote from Ian McKellen, but in fact, McKellen had been responding to a question only about openly gay actors. It was a pretty galling gaffe, given that men like Elton John, Dustin Lance Black, and Howard Ashman had paved the way for Smith with their Oscar wins.

Taylor Swift Mistakenly Thinks Red Wins Album of the Year (2014 Grammys)

Swift had already taken home the Grammy for album of the year for her debut, Fearless, but in 2014, she clearly thought another was coming for Red. As Alicia Keys read aloud the actual winner, Daft Punk’s Random Access Memories, she held the first syllable for a brief second, causing Swift to think Red had triumphed. Her priceless reaction went viral.

Chrissy Teigen Becomes a Meme (2015 Golden Globes)

Teigen was moved to tears by her hubby John Legend’s win for the song “Glory” from Selma. Unfortunately for her, the camera caught her at precisely the wrong moment, serving a facial expression that seemed more like an uncomfortable grimace. “Sorry I don’t practice my cry face okay,” she tweeted. “It’s been 5 minutes and I’m a meme.”

Miguel Jumps and Lands on a Girl’s Face (2013 Billboard Music Awards)

During his performance of “Adorn,” Miguel leapt across a mosh pit of audience members, from one section of the stage to another. But it was anything but clean, as he ended up basically clotheslining a woman with his leg and landing with his crotch in her face.

Katy Perry Falls Four Times (2008 MTV Latin America Awards)

At the end of a performance of her first hit, “I Kissed a Girl,” Perry jumped atop a giant cake. That part was on purpose, but it’s hard to imagine the rest was. She and the floor were both so covered with icing, she fell not once, but four times before crawling away.

Joe Jonas Falls and Cuts His Hand on Glass (2007 AMAs)

Hoping for a badass entrance, the JoBros began their performance with three panels of glass that shattered in front of each of the boys. But Joe tripped as he crossed the threshold, falling to the ground and cutting his hand on the broken glass. He got up and kept the performance moving, despite visibly bleeding from the gash on his palm. Backstage he played it cool, saying, “Just a little blood, but, whatever, rock and roll.”

Random Man inches Offstage Behind Neil Patrick Harris (2013 Emmys)

As NPH, the night’s host, delivered a line heading into a commercial break, an anonymous man behind him looked like a deer in headlights as he realized he was on camera. The true gold was in the man’s decision to solve this issue by slowly side-stepping out of frame. “Awkward Man,” as the internet dubbed him, was later identified as Paul Greenberg, a writer on the awards show. In other words, there’s a good chance it was intentional.

Streaker Crashes the Stage (1974 Oscars)

As cohost David Niven prepared to welcome Elizabeth Taylor to the stage, a naked man ran across, throwing up a peace sign to the camera. After about 30 seconds of stunned laughter from the crowd, Niven responded, “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?”

Seth MacFarlane Sings “We Saw Your Boobs” (2013 Oscars)

Many were outraged by a musical number from MacFarlane, the night’s host, that listed the many times that famous actresses — from Meryl Streep to Halle Berry — had bared their breasts on film. Naomi Watts and Charlize Theron, both mentioned in the song, seemed to be among those who deemed the number despicably sexist. In reality, they were in on the bit, having pre-recorded their reactions.

Faith Hill (Fake) Freaks Out When Carrie Underwood Beats Her (2006 CMAs)

When Hill lost out to Underwood for the Country Music Association’s Award for female vocalist of the year, she threw her hands in the air and mouthed, “WHAT?!?” Home viewers thought she was having a freak out, but Hill claimed the next day that it was in jest. “The idea that I would act disrespectful towards a fellow musician is unimaginable to me,” she said. “For this to become a focus of attention given the talent gathered is utterly ridiculous.”

The Pussycat Dolls’s Melody shows Up Mid-Performance (2006 AMAs)

If the worst thing that had happened during the Dolls’s performance of “Buttons” was the chair that fell over halfway through, the number wouldn’t have been a total disaster. But when group member Melody Thornton strutted onstage with only 40 seconds in the song remaining, ish got weird real fast. Totally off-pitch, she began screeching over top Nicole Scherzinger as the other girls continued their choreography and viewers at home wondered WTF was happening

Jennifer Lopez Falls on Her Butt (2009 AMAs)

J.Lo attempted a big stunt during her performance of “Louboutins,” as she used her backup dancers like human stairs. That went off without a hitch, but when she jumped off at the end, she couldn’t stick the landing. She ended up on her butt, though she was back up in less than a second.

James Franco and Anne Hathaway … Host (2011 Oscars)

Pretty much nothing about Franco and Hathaway’s joint hosting gig worked, which led to tons of uncomfortable moments. Franco seemed to have no interest in being there, and Hathaway’s theater girl earnestness kicked off the “Hatha-hate” period of her career. A lame bit in which Hathaway donned a tux and Franco wore a dress summed up the night’s quality.

Lil Mama Crashes Jay-Z and Alicia Keys’s Performance (2009 VMAs)

Kanye West got so much attention for crashing Taylor Swift’s speech at the 2009 VMAs, people tend to forget that the same night, Lil Mama committed the same crime. As Jay and Keys performed “Empire State of Mind,” Lil Mama got on stage and posed alongside them for the ending. Jay called the moment “outta line” and the “Lip Gloss” singer apologized, saying the song had her “emotions running high.”

Angelina Jolie Kisses Her Brother on the Red Carpet (2000 Oscars)

Jolie made some people very uncomfortable when she locked lips with her brother James Haven, who was her date for the evening. When she won her Oscar later that night for Girl, Interrupted, she doubled down, saying, “I’m so in love with my brother right now.” The actress later clarified things. “It wasn’t some odd open-mouthed kiss,” she told People. “It was disappointing that something so beautiful and pure could be turned into a circus.”

Adrien Brody Deep Kisses Halle Berry (2003 Oscars)


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