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Celebrity Awkward Moments that Happened on Live Television

Celebrity awkward moments always remind us that they are people, too.

Some of those moments are simply too cringey, though. The worst is when it happens live on air and they’re suddenly trapped in embedded in pop culture history forever. Television seems to capture the worst in all of our favorites and if the camera crew was nice, they’d stop rolling the cameras the moment it happens. However, that’s simply not practical for show biz and so everything must go on! Between interviews, red carpet moments, talk shows, and more, there’s always a fresh moment for us to get second-hand embarrassment from.

Check out some of the best of those moments here.

Bill O'Reilly Causes a Walk Off on The View

The View hosts have never really shied away from being a bit controversial. They love to tackle big topics and break down real world stories for their audience. Part of these conversations is bringing guests onto the show to elevate these discussions. However, even these hosts have their limitations. One time, they brought Bill O’Reilly into the studio and were offended by some of his disrespectful statements and his attitude. It caused Whoopi and Joy Behar to walk off the stage!

Tom Cruise Jumps on Oprah's Couch

Love makes us all do crazy things. However, Tom Cruise may have gone a little whacky while on Oprah. It was all in the name of love, too. Oprah began to talk about actress Katie Holmes. At the time, Tom was really into Katie. He was overjoyed to be talking about her and jumped on the couch to show that. What’s even better is that by the end, Oprah even announces that Katie is in the studio and brings her out. While it was sweet, jumping on the couch was totally awkward, especially when Katie herself was there!

Jessica Simpson Drunk on Ellen

Being an interviewer isn’t always easy, especially when you’re live on air. For Ellen Degenres, this means being ready to keep the conversation on track even when her celebrity guests seem to be derailing. On her show Ellen, Jessica made multiple comments that just seemed off. She even was bickering with Ellen at one point, who was trying to keep composure. Fans noticed right away, but the tension between the pair was definitely awkward. Later, Jessica admitted to being drunk on air.

Ari Gets Slapped by an Angel Wing

The Victoria’s Secret Fashion Show used to be an event that everyone would anticipate. While it’s no longer being put on, when it was, it was the talk of the town for days. It featured models donning the new looks of the season, but also had performances from our favorite celebrities. Ariana Grande was one of those performers and the livestream captured a super awkward moment for the star. She ended up getting whacked with one of the angel wings that the models wear. So much for keeping the fantasy! She surely got a dose of reality.

Gordon Ramsay's Creepy Moment with Sofia Vergara

Your favorite chef may not be as family friendly as you may think. He totally made everyone cringe when he made certain remarks to actress Sofia Vergara. The pair made an appearance on The Late Show with Jay Leno in 2019. He kept making awkward innuendos and remarks. He even went as far as to touch Sofia at times. Sofia closes off during the interview which makes the whole dynamic even more unsettling to watch.

Kanye West Steals Taylor Swift's Mic

One of the most awkward moments on live television was the moment that Kanye West interrupted Taylor Swift giving an award acceptance speech at the VMAs. He jumped right up on stage and took the microphone from her. He said that Beyonce deserved the award more before letting Taylor finish. Not only was this incredibly awkward for Taylor, but what would follow would be a long string of pop culture history that seems to forever be unraveling.

Amy Schumer Falls and Ignored

Kim Kardashian and Kanye West aren’t known for being particularly empathetic as people. However, you would think that if someone falls in front of you that you would try to help at least a little bit. When Amy Schumer fell straight on her face on the red carpet, the former couple totally ignored her. It really is them showing their true colors, but also showed how much people didn’t care if Amy fell. She claims this was all just a prank, but maybe she’s just embarrassed by the apathy that she experienced.

Drew Barrymore Flashes David Letterman

Drew Barrymore was perceived as incredibly sweet and innocent for a long time in her career when she was younger. Like many young stars, the time would come for her to break out of that stereotype. To do so, she started rebelling and acting out a little bit. Most notably, she flashed David Letterman live on air. She even danced on his desk. It was sort of awkward, especially since she was only 20 and he was 48. However, the camera kept rolling!

Seinfeld Rejects Kesha's Hug

Not all stars are created equal! More accurately, not all stars see themselves on the same level as each other. Kesha is one of the biggest pop stars in music and Jerry Seinfeld is truly a household name. What happens when these two meet? Who will prevail? Well, it turns out that Seinfeld actually rejected Kesha. She went in for the hug on a red carpet and Seinfeld told her no, thanks! She left defeated and probably feeling a bit awkward about the public occurrence.

Madonna Kisses Britney and Christina

We’re not sure if this is awkward or just incredibly unexpected. After a crazy performance at the 2003 VMAs, a kiss would shock the world. Madonna and Britney Spears ended up actually kissing live on camera. Then, Christina Aguilra joined in, kissing Madonna! All this happened so fast that no one could keep up. The moment was captured on camera and is even being sold as an NFT by the photographer. The VMAs seem to always be having the wildest pop culture moments!

50 Cent's Baseball Pitch Fail

Maybe musicians should, like, stick to music. 50 Cent has one of the most embarrassing on camera moments of all time. On camera, during a baseball game, he threw one of the lousiest pitches. Of course, he’s not known for his athletic skills or anything, but everyone thought he would do better than… that. It was before a Mets game that he threw what many would consider to be the worst pitch in baseball history. Apparently, he still thinks about it, too.

"Cash Me Outside" Girl On Dr. Phil

As the years go on, this moment only gets increasingly more cringey. In 2017, Danielle Bregoli became a viral sensation and meme. However, it wasn’t exactly a good thing. She became known for her terrible attitude and ‘blackfishing’ controversies. On Dr. Phil, she delivered the famous “Cash Me Outside” line that put her on the map. It was so awkward and laughable that people began mocking her all over the Internet. However, it turned out to be a success for her since she’s now under the artist name “Bhad Bhabie” making music.

Nancy O'Dell Makes An "A Lot of Men" Comment to Taylor Swift

We’re not sure who this is actually embarrassing for, but we know this pop culture moment definitely created a lot of strained and awkward tension in the air. Nancy O’Dell was interviewing Taylor Swift on the Grammys red carpet. She ended up making a comment about how Taylor would be leaving that night with “a lot of men.” Taylor was shocked and gave her a death stare for the condescending comment. While it may have seemed embarrassing for Taylor, it’s probably more embarrassing for Nancy to forever be disliked by the pop princess.

Eminem is Assaulted by Bruno's Butt

This time we are not talking about Bruno Mars! Instead, we’re talking about Sasha Baron Cohen’s odd little character “Bruno” who is caught up doing quite some odd pranks. At the 2009 MTV Movie Awards, his pranks caused quite an awkward moment for everyone. Bruno had quite the stunt: he flew high over the audience with his butt mostly exposed while wearing white wings! He ended up falling into Eminem’s lap with his butt in the rapper’s face. What really made it awkward, though, was his reaction. He immediately stormed out of the award show.

Charlie Sheen's "Winning" Interview

The world watched Charlie Sheen spiral in real time and didn’t really know what to do about it. When Charlie was working on Two and a Half Men, he was also coping with a serious addiction problem. Publicly, he was speaking out with ludicrous statements, so the network had to pause production and remove Charlie from the cast. However, following this, he had a concerning interview where he declared that had tiger blood in his veins. Charlie also coined a catchphrase of “winning” that would become a viral sensation. It was super awkward, especially because Charlie has admitted to being ashamed of those events ever since he’s recovered. It must be really painful to look back at it.

Ellen Forgets Katy Perry's Marriage

Sometimes it is super impressive that Ellen is able to keep so much information about celebrities in her head at all times. She’s typically spot on when doing her interviews for her TV show. However, that almost makes it even more awkward when she does slip up. In an interview with Katy Perry, Ellen forgot that the singer had been married before. The worst part is that Ellen had apparently even sent Katy gifts for the wedding… guess she simply wasn’t paying attention.

Sacha Cohen Baron Spills Ashes on Ryan Seacrest

Ryan Seacrest may just be known for being possibly one of the nicest guys in Hollywood. So, when he was the target of a crazy prank, he took it all in stride. At the Oscars red carpet, Sacha Cohen Baron ended up spilling an urn of ashes all over Seacrest! However, it was all just a silly prank. In the moment, though, no one had any idea that it was fake and it became this incredibly awkward and tense occurrence.

One Direction Is Asked About "Larry Stylinson"

If you aren’t aware, there’s this theory that Louis Tomlinson and Harry Styles had a relationship while in the boyband One Direction together. It’s something still speculated about today, but when the band was active it was highly debated among the fanbase. However, it was rarely acknowledged publicly by the band unless asked about it directly. While live on RTE One’s Late Late show, they were specifically asked about ‘Larry Stylinson’ and fans were shocked by the question. Louis ended up denying the conspiracy, but fans still wonder sometimes.

Elon Musk's Cyber Truck Fail

Elon Musk may be incredibly controversial, but he does know how to make a statement with his inventions. When unleashing something big, Elon often makes public presentations. He thought that his Cybertruck was going to be that next big thing. Boldly and confidently, Elon was ready to show it off. Unfortunately for him, though, it all went wrong. He advertised the truck as having bulletproof glass, but a few window smashes in and it all came shattering down around him. Arguably, the whole truck was kind of ugly anyway.

Justin Timberlake Photobombs Emma Stone

The Oscars in 2017 were certainly ones to be remembered. One of the best parts of any award shows are the crazy moments and interviews that happen on the red carpets. However, even these aren’t immune to awkward moments and encounters. For Emma Stone, this means being totally photobombed while trying to do an interview with ABC. Justin comes up behind her with the strangest expression, distracting her from what was going on.

Jennifer Garner Fights About Grammar

Have you ever admittedly fought about something you believed you were right on just for it to turn out you were wrong? Jennifer Garner was confident that the word “snuck” wasn’t a word. We’re no grammar experts, but apparently it is, but only in certain situations. She awkwardly corrected Conan O’Brien’s grammar live on air, saying he was wrong for using “snuck.” She even made a dig about the fact that Conan went to Harvard University.

Jimmy Fallon Afraid of Being Canceled During RuPaul Interview

Interviewers notoriously need to learn how to navigate tricky situations especially when they’re live. It’s so easy to have a little slip-up and say something that will offend the person you’re talking with. More importantly, it’s key to understand what you’re talking about in the face of complex and nuanced social issues. You never know what topic may come up! While interviewing RuPaul, Jimmy Fallon referred to him as a drag queen. While that was a totally correct descriptor, RuPaul’s reaction made Jimmy think he was getting canceled. RuPaul ended up just correcting him to say he’s the “queen of drag,” but that could have been really bad. Totally awkward for Jimmy.

Ryan Seacrest Tries to High Five a Blind Guy

This particularly awkward moment consumes our thoughts sometimes. While filming American Idol, Ryan Seacrest’s totally friendly self was trying to make a nice gesture. He lifted up his hand for a high five to express some congratulations. However, the contestant happened to be blind! Ryan awkwardly kept his hand up for several moments before processing what had just happened. Instead, he tries to recover from the embarrassment by just lowering his hand and grasping the contestant’s, and raising the contestant’s hand in the air. He shakes it around for a second before releasing it again.

Janet Jackson's Wardrobe Malfunction

At crazy and highly promoted events like the Superbowl, anything that goes wrong is sure to be magnified and have a million eyes on it. That’s why it’s so important to make certain that absolutely nothing will go wrong. Unfortunately, when travesty strikes it does so hard. During her Superbowl performance in 2004, Janet Jackson was the victim of a wardrobe malfunction that left her fully exposed. Her performing partner — Justin Timberlake — was pulling at a piece of her outfit, but it wasn’t supposed to fully leave her naked during the performance.

The Bachelor Dumps His New Girl Live at the Reunion

You either love The Bachelor or you hate it, but either way, you can’t deny that some of the drama is just oh-so enticing! You really never know which direction the show will take. In the show, the bachelor is supposed to end up with the love of their life at the end. This is a bit of an idealistic approach considering that it is a reality show and there will always be a bit of TV magic. Plus, you can’t expect all of the relationships to last forever. However, it was truly a first when during the reunion episode, Jason fully rejected Melissa for a different contestant!

Drew Barrymore Flashed David Letterman on His Birthday

The interview started when David asked Drew about her birthday. She seemed very friendly and happy telling the details about her party. Things were quite a little bit awkward when Drew rebelled and acted out. She re-enacted her dance scene at her birthday party on the show. She jumped on his desk and started dancing, then, suddenly flashed herself in front of David on air. There was a moment of shock from David and sort of awkward knowing that Drew was only 20 at that time.

Kanye West Ruined Taylor Swift’s Speech at the VMAs

Taylor Swift won Best Female Video at the VMAs in 2009. However, during her acceptance speech, Kanye West did interrupt her and said that Beyoncé deserves the award. Not only was this extremely unpleasant for Taylor, but it would also set off a long series of events in pop culture history that seem to be constantly falling apart.

Nicki Minaj’s Wardrobe Malfunction At The 2014 VMAs

Nicki obviously had a wardrobe malfunction during the performance of “Bang Bang” at the 2014 VMAs. At Ellen’s Show, Nicki explained that since Jessie and Ari were wearing black and white, she quickly changed from her Anaconda outfit to a black one. As a result, she was completely obscured by the curtain and could not see anything while changing with her whole team. In the end, Nicki said, “Right before it was time for me to walk out, they went to zip it up, and … right there, I thought I died. I didn’t have any underwear on!”

Madonna Fell While Performing At The 2015 Brit Awards

On a night when Sam Smith and Ed Sheeran each took home two awards, pop singer Madonna tumbled off the stage during her performance at the 2015 Brit Awards. Apparently, after a dancer tried to take off the cloak Madonna was wearing at the beginning of her routine, she fell awkwardly down a flight of steps and continued singing, “Living for Love.” She, then, posted on Instagram, “Armani hooked me up! My beautiful cape was tied too tight! But nothing can stop me and love really lifted me up!”

Doja Cat Missed Her Grammy Win Announcement

Doja Cat ran to the platform and had trouble walking up the stairs due to being on crutches. It was also noticeable that she flung her vaporizer on the floor and then delivered her speech after missing the announcement of her Grammy win for Best Pop Duo/Group Performance for “Kiss Me More” because she was in the bathroom. SZA (her collaborator in the song) joked at her, saying, “Girl, you went to the bathroom for like five minutes. Are you serious?” Doja responded, “Listen, I have never taken such a fast p— in my whole life.

Will Smith Slapped Chris Rock On Stage At The 2022 Oscars

Chris Rock appeared on the Oscar stage to give the Best Documentary award. He started off by cracking a few jokes about the viewers of the program, including Pinkett Smith, whom he referred to as “G.I. Jane” because of her short hair due to alopecia. Rock had just finished his joke when Smith entered the stage and smacked him across the face. He then walked back to his chair and yelled at Rock, “Keep my wife’s name out of your fucking mouth.

Melanie Griffith Was Asked About Fifty Shades of Grey During The 2015 Oscars Red Carpet

Dakota Johnson walked the red carpet with her actress mother, Melanie Griffith, before presenting at Sunday’s Academy Awards. However, during the ABC pre-show interview with the host, Lara Spencer, the two engaged in an incredibly unpleasant exchange. When Spencer questioned Griffith about whether she had seen the R-rated movie “Fifty Shades of Grey,” Griffith said, and goes on with it, saying, “I don’t think I can; I think it would be strange. She’s a really good actress; I don’t need to see that to know how good she is.”

Cara Delevigne Was Mocked About Her Presence On "Good Day Sacramento"

Despite acknowledging to Kiss FM that she has become accustomed to the attention that celebrities bring, Cara Delevigne will dispute misunderstandings about her work ethic. When Cara promoted her movie, Paper Towns, an adaptation of the best-selling book by John Green, on the American morning show, Good Day Sacramento – she persevered at first, plausibly replying to a succession of really surprising questions, which culminated in a busy month of promotion. Her sarcasm, however, did not impress the anchors, who eventually called her out, broke off the interview, and even advised her to “take a nap, maybe drink a Red Bull.”

Red Carpet Interviewer At The Grammys 2015 Teased Taylor Swift

Taylor Swift may write and perform songs about her romantic relationships, but she doesn’t like it when people make assumptions about them. When a reporter for Entertainment Tonight, Nancy O’Dell, made a joke about Taylor leaving the night with “lots of men’. Swift gave an icy look before denying anything and directly responded with, “I’m not going to walk home with any men tonight. I’m going to hang out with my friends, and then I go home to the cats.”

Zac Efron's Condom Was The Star Of The Lorax Premiere

When the condom escaped from the tight grasp of Zac Efron’s denim and sprang out onto the red carpet at the premiere of The Lorax, like the movie star he truly is, his shallow pant pockets betrayed him. When the star mouthed to the publicist, it was clear to hear the star’s inaudible humiliation. He then said in his interview with Today, “I never really had a pocket checking policy prior to going onto the red carpet before, but now we’ve fully instated one.”

Miley Cyrus' 2013 VMAs Performance With Robin Thicke

The year 2013 saw the emergence of twerk. That year, Miley Cyrus from her Bangerz era wreaked havoc while clad in a nude latex bikini at the MTV VMAs by twerking on the lions of Robin Thicke, the singer of “Blurred Lines.”  In Thicke’s interview with Oprah Winfrey, the singer claimed that he did not think of Cyrus’ performance as sexual because he allegedly “did not see it” because he was so busy singing that he didn’t pay attention to what Miley was doing at all.

Steve Harvey's Miss Universe Mistake

When Pia Wurtzbach, Miss Philippines, should have won Miss Universe, Steve Harvey mistakenly declared Ariadna Gutierrez, Miss Colombia, as the victor. In what is likely to be the most awkward few minutes of live television ever, the TV host quickly realized his mistake after leaving the stage and jumped back out to make it right. He controlled the crowd by saying, “OK folks … I have to apologize. Let me just take control of this. I will take responsibility for this. Do not take it against the ladies. It was my mistake. It was on the card.

When Ashlee Simpson Lip-Synched On SNL

Looking back, there was probably a good reason why Ashlee Simpson was a musical guest on SNL, and it seemed a little unbelievable at the time. In 2004, Ashlee was about to perform her song “Pieces of Me” when the lyrics and vocals started to play. Ashlee attempted to shake off the awkward lip-syncing reveal, but she eventually just left the stage. Ashlee cleared up the incident in 2018 with Andy Cohen, stating that she should have backed off instead of performing; she lost her voice during that time.

Janet Jackson’s Wardrobe Malfunction During Super Bowl 38

When Janet Jackson had one of the most noticeable “wardrobe malfunctions” at one of the biggest events in the world. In 2004, her career suffered as her breast was shown during her performance with Justin Timberlake at Super Bowl 38 after Timberlake tore a portion of her outfit. The show turned out to become one of the most notorious instances in the history of pop culture. Janet had been quiet about the issue until her interview with Oprah Winfrey in 2006.

Anne Hathaway’s Awkward Interview On The Today Show For Les Misérables

In 2012, Anne Hathaway appeared on The Today show to promote Les Misérables, shortly after the paparazzi captured a photo of her skirt flying up as she exited a car. Lauer decided to commence the conversation by pressuring Hathaway into talking about it. Hathaway handled the situation by saying, “I was very sad that we live in an age when someone takes a picture of another person in a vulnerable moment, and rather than delete it, and do the decent thing, sell it. And I’m sorry that we live in a culture that commodifies the sexuality of unwilling participants.”

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