24 Superrrrr Cringey Celeb Moments
In one of the most recent examples, Madonna reportedly chastised a fan for sitting during her concert in Los Angeles this month, saying, "What are you doing sitting down over there?" Walking forward and apparently realizing the person was in a wheelchair, Madonna said, "Oh, okay. Politically incorrect. Sorry about that. I'm glad you're here."
According to a fan, "There's a part where during the show she asks everyone to stand up. It's not about who's sitting/standing during the entire show. Just 1 section she asks for participation. And this time she embarrassed herself."
Another Madonna one for ya — back in 2015, she posted a photo that seemed to be of herself to promote her album Rebel Heart, writing, "I look Kewl.........❤️#rebelheart." Later, TikTok user @ameliamgoldie claimed that the photo was actually of her — and that Madonna had photoshopped her own head on top.
Ben Affleck made headlines in 2021 after a woman named Nivine Jay posted a TikTok claiming she had matched with Affleck on Raya but unmatched him because she thought his profile was fake. She then alleged that Affleck had reached out to her on Instagram, sending her a video in which he said, "Nivine, why did you unmatch me? It's me!" This might all seem a little far-fetched...except she posted the video Affleck sent.
Jennifer Lopez not being recognized in the Bronx still lives rent-free in my mind. Shooting a clip for American Idol, she took a camera crew to the neighborhood she grew up in, pointing out her old home. A man standing outside, confused at her presence, asked who she was. When she answered that she was Jennifer Lopez, he seemed either unimpressed or unaware of who that was.
Watch the awkward moment for yourself here.
Another celeb clip that alwayssss makes me cringe is this Complex feature with Bella Hadid. While talking about sneaker turn-offs, Hadid awkwardly calls men courting her "homeboy," uses a bunch of '90s slang, and trails off when saying "homeboy's gonna like....get it." The last phrase in particular became a huge meme online.
It's kind of hard to understand *quite* how awkward this moment is without watching the clip, so go ahead and do so here.
Adam Levine got in hot water in 2022 after multiple women came forward with flirty messages he had sent them, even though he's married. While that in itself is embarrassing, it's the contents of the messages that caused people to roast him online. "Holy f–k. Holy f–king f–k. That body of yours is absurd," he allegedly wrote in several messages. "F–kkkkkkkkk I'd do anything for it," he wrote in another. Fans reposted the comments, captioning them with their own scenarios like "Me when I see a Klondike Bar."
Levine released a statement admitting to using "poor judgment in speaking with anyone other than my wife in ANY kind of flirtatious manner." However, he denied having an affair. 'I did not have an affair, nevertheless, I crossed the line during a regrettable period of my life. In certain instances it became inappropriate.'
One celeb interview clip I can hardly even force myself to watch, it's so awkward, is Iggy Azalea's infamous freestyle. The clip is from back in 2013 when Iggy Azalea was asked to freestyle on the radio show Sway in the Morning. Iggy awkwardly "raps" with no beat, using somewhat stilted lyrics she'd later put in her song "New Bitch," completely switching to a blaccent when she started the verse. The freestyle was relentlessly mocked and memed online when it resurfaced in 2014, with even Iggy later calling the verse "trash."
This isn't Iggy's only freestyle fail, either.
Watch the clip here (the rap starts at 2:21).
When Bow Wow flexed his luxurious travel plans on Instagram, it seemed like a pretty regular celeb post, complete with a photo of a private jet and the caption, 'Travel day. NYC press run for Growing Up Hip Hop. Lets gooo." However, he was embarrassingly exposed when a Twitter user posted a photo of Bow Wow flying commercial, writing, 'So this guy lil Bow Wow is on my flight to NY but on Instagram he posted a picture of a private jet captioned 'traveling to NY today.'"
In one of the most embarrassing social media fails to me, Mia Farrow once posted a happy birthday message to her daughter Quincy, accompanied by a photo. Innocent enough, right? Except she forgot to crop the photo and posted it with the search bar visible. To find the photo, she'd searched "Mia Farrow and her black children."
In another online fail, back in 2014, Rita Ora tweeted that she'd release new music if she got 100,000 retweets. It only got 2,000 retweets, and Ora deleted the tweet. She then tweeted, "By the way my Twitter got hacked somebody is threatening to release new music I've worked really hard on. Nothing comes out until I'm ready."
I also always laugh at the time Kim Kardashian posted an old bikini photo of herself on Instagram, then claimed her daughter North (then two years old) had posted it, writing, "North posted this while playing games on my phone. Not sure why or how she chose it but I'm not complaining! LOL I deleted it so now reposting it myself!"
Kim later stood by her claim, writing that North was "always following and unfollowing people on Twitter" and that she "deleted it and then put it back up because why not, haha!!!'
One more Instagram example – when Kardashian hanger-on Jonathan Cheban posted a story on Instagram asking "Should I go live later?" and the answer was, overwhelmingly, "no."
In yet another embarrassing social media snafu, Charli D'Amelio spotted #HereForCharli trending on Twitter in 2021 and tweeted, "Oh my goodness, you are all so sweet to me. You have no idea how much your kind words warm my heart i am so lucky to have you all by my side!! I love you bebs." However, she quickly deleted the tweet when fans pointed out the hashtag was actually for Charli XCX, whose friend, the musician and producer, Sophie, died suddenly.
Jim Carrey's two-minute-long video declaring his love for Emma Stone is definitely one of the more bizarre things I've seen a celebrity do, and whether or not he was joking, it had everyone cringing. In the video, Carrey says, "If I were a lot younger, I would marry you, and we would have chubby little freckle-faced kids. We'd laugh all day long and go camping, play Yahtzee, tell ghost stories by the fire. And the sex..." He trailed off, clearly thinking about sex with Emma Stone.
Emma took the video in stride, later saying of the video, "Right before that video came out, we were at the MTV Movie Awards. Jason Sudeikis hosted … There was like five of us, and we just went on this tangent of talking nice behind Jim Carrey's back. Jason was talking about how great [Carrey] was when he went to 'Saturday Night Live' and how he was just like a comedic genius. Everyone was kind of weighing in, like 'He's the best. He's amazing.' And so when [the video] happened, we all kind of talked to each other like, 'Weird, that was the guy we were lauding for, like, 30 minutes.' Have you ever done that? Just all sat around a table saying nice things about one person? It was the greatest thing. You walk away, and you were just like, That felt so good, to talk about how wonderful someone is."
Watch the video here.
Ariana Grande has a ton of tattoos, and it was no surprise when she got one as an homage to her song "7 Rings." She posted the tattoo — written in Japanese characters — online, and fans quickly pointed out her tattoo actually translated to a charcoal grill. Which is especially awkward considering Ari is vegan.
In response to online mockery, she tweeted, 'Indeed, I left out 'つの指' which should have gone in between. It hurt like fuck n still looks tight. I wouldn't have lasted one more symbol lmao. But this spot also peels a ton and won't last so if I miss it enough I'll suffer thru the whole thing next time.' In another tweet, she wrote, 'Pls leave me and my tambourine grill alone. thank u.' She later had the tattoo "fixed," though it still didn't correctly translate to "7 Rings."
In 2009, Scott MacIntyre became the first blind person on American Idol, leading to a hilariously awkward moment with Ryan Seacrest. After MacIntyre performed and received a golden ticket in the first round, he came out of the audition room, where Seacrest was waiting. Seacrest then attempted to high-five him, before remembering MacIntyre wouldn't be able to see his hand and slowly lowering it.
Watch the video here.
I still can't believe the infamous Best Picture mix-up of 2017 happened, and this list wouldn't be complete without it. Back in 2017, Faye Dunaway and Warren Beatty presented the award, with Beatty expressing visible confusion after reading the card (later, he would explain that it was the card for the Best Actress award, which went to Emma Stone for her role in La La Land and had already been announced). Simply seeing La La Land, Dunaway announced that they had won Best Picture. The La La Land producers even made their speeches before there was an awkward commotion onstage, and it was eventually revealed that Moonlight had actually won Best Picture.
Watch the video here.
This isn't the first time something similar happened at a major awards show. In 2015, Steve Harvey also announced the wrong winner in the Miss Universe pageant, and it was super, super awkward.
If you want to cringe, watch the clip here.
But perhaps the most infamous celeb-messing-up-on-live-TV moments? Ashlee Sympson's lip-synching scandal on Saturday Night Live. When the wrong track began to play (the same one she'd already performed), Simpson did not sing and instead did a strange jig as the band played around her. The moment would go down in SNL history and significantly affect Simpson's career.
Watch the clip here:
Finally, Charlie Puth's whole 2018 Billboard interview is a bit cringeworthy, but I will forever be haunted by him saying, "I'm hungies!" and making his driver take him out to eat. Please, Charlie, for all of our sakes, never say that again.
What embarassing celeb moment lives in your head rent-free? Let us know in the comments!
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