24 Times Celebrity Were So, So, SO Cringe

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Celebs — they're just like us! Which means they have some pretty embarrassing, awkward, and overall cringy moments. Except since they're celebs...well, they're usually a LOT bigger. Here are 24 times celebs made me make this face:

Woman in striped top making a funny face with scrunched nose and smile
NBC

1.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."

closeup of madonna

2.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.

  Karwai Tang / WireImage via Getty Images
Karwai Tang / WireImage via Getty Images

3.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.

Man in a black suit without a tie at an event
Leon Bennett / WireImage via Getty Images

4.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.

Woman conversing about past residence, mentioning the name "Jennifer" several times in a stairwell
Fox

Watch the awkward moment for yourself here.

5.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.

bella in front of a wall of shoes
Complex

It's kind of hard to understand *quite* how awkward this moment is without watching the clip, so go ahead and do so here.

6.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."

Man with buzzed hair and tattoos on neck wearing a dark suit at an event

7.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."

iggy in the radio show studio

Watch the clip here (the rap starts at 2:21).

8.Another questionable interview moment that went viral comes from Liam Payne's interview with Logan Paul. Speaking about his first solo single, "Strip That Down," Payne claimed, "I think it outsold everybody within the band, and I was the last to go [solo]. And I never expected that." Fans were quick to prove him wrong, posting receipts that showed both Harry Styles and Zayn Malik's debut solo songs ("Sign of the Times" and "Pillowtalk," respectively), along with other songs they've released, were far more successful. He was also mocked for his claims that the band formed around him as the star.

Man with a smile wearing a tuxedo with a black bow tie and contrasting white jacket lapels

9.In another somewhat embarrassing interview, Payne talked about how he wouldn't know what to say to Harry Styles if he saw him now, then said their music was incredibly different, adding, "I'm like the antichrist version of what Harry is."

Two singers, one with tattoos, performing on stage with microphones
Kevin Winter / Getty Images for iHeartMedia

10.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.'"

closeup of bow wow sitting down and wearing a baseball cap
Paras Griffin / Getty Images

11.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."

closeup of mia
Jamie Mccarthy / Getty Images

12.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."

closeup of rita
Gilbert Carrasquillo / GC Images via Getty Images

13.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!"

14.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."

Selfie of a man in bed with a poll overlay asking if he should go live, showing 47% yes, 53% no
foodgod / Instagram

15.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.

closeup of charlie d'amelio
closeup of charlie d'amelio
closeup of charlie xcx
closeup of charlie xcx

Tiffany Rose / Getty Images for Family Film and TV Awards, Steve Granitz / FilmMagic via Getty Images

16.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.

jim talking into the camera

Watch the video here.

17.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.

Woman with sleek ponytail, elegant necklace and earrings, looking at camera

18.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.

ryan reaching down to grab scott's hand to give a high five
Fox

Watch the video here.

19.There's little more embarrassing than a failed PR stunt, and Garth Brooks is perhaps one of the best examples of that. In 1999, Garth Brooks, then a successful country artist, decided to launch an alter ego — Chris Gaines — in preparation for a planned movie about the murder of Gaines to be called The Lamb.

Garth Brooks wearing a cowboy hat and light jacket at an event with movie posters in the background
James Devaney / WireImage via Getty Images

The fictional Gaines was a rock artist, and Garth, as Gaines, appeared as a musical guest on SNL and in a mockumentary for Behind the Music. Garth also released an album as Gaines ahead of The Lamb film titled, Garth Brooks in...the Life of Chris Gaines. People were pretty confused about the whole thing, and when the album didn't sell as well as expected, The Lamb was dropped entirely. The whole thing was super awkward, especially the pseudo-emo photos that came out of it.

Panelists seated at a table with promotional posters for "The Life of Chris Gaines" in the background
Steve Granitz / WireImage via Getty Images

20.CeeLo Green also attempted a disastrous reinvention, where he tried to rebrand himself as "Gnarly Davidson" back in late 2016, releasing the song "Fuck Me, I'm Famous" as his alter ego. He then attended the 2017 Grammys as Gnarly, dressed in all-gold. He later claimed he wasn't at the Grammys, telling TMZ, "That’s somebody else altogether, man,” really committing to the bit. After releasing a second song about wanting to be with Beyoncé, Green apparently abandoned the Gnarly Davidson persona.

Person in a full-body metallic gold outfit with a matching mask, giving a thumbs-up
Axelle/Bauer-Griffin / FilmMagic via Getty Images

21.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.

la la land producers on stage being told that moonlight was the actual winner
ABC

Watch the video here.

22.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.

harvey announcing colombia as the winner and then apologizing and announcing miss universe is philipines
Fox

If you want to cringe, watch the clip here.

23.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.

Ashlee Simpson on "SNL"
NBC

Watch the clip here:

24.Finally, Charlie Puth's whole 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.

closeup of charlie
Leon Bennett / Getty Images

What embarassing celeb moment lives in your head rent-free? Let us know in the comments!

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