Most Embarrassing Celebrity Moments

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5 days ago

Back in 2021, Don Cheadle appeared on Kevin Hart's Hart to Hart podcast, and they had a somewhat awkward moment after Kevin couldn't hide his disbelief when Don revealed his age. 'You know, I'm 56 years old,' Don said in the interview, with Kevin dramatically exclaiming: 'Damn!' However, when Don's reaction was to just stare at him totally deadpan, Kevin found himself repeatedly apologizing and trying to explain himself. The instant regret is palpable!
Watch the clip here:
And speaking of instant regret, Camila Cabello could not hide her sheepishness when she seemingly thought better of a NSFW joke as soon as she made it on the 2024 Met Gala red carpet. When a Variety reporter asked the singer about her and Doja Cat's wet-look outfits, Camila quipped: 'The girls are wet tonight,' before seductively putting her finger to her mouth. Immediately afterward, Camila said: 'Sorry,' and when another reporter said: 'You went there!' The star awkwardly repeated: 'I did, I'm sorry.'
Meanwhile, I think of Shawn Mendes's 2019 103.5 KTU radio appearance literally any time I hear the word 'amazing,' with the singer smiling broadly as the host praised him for all he does for mental health awareness. She then tells him: 'Myself included, I struggle with anxiety,' to which Shawn inappropriately says in response: 'Amazing.' And just like that, a new meme was born.
Watch below:
But it's not just Shawn going down in meme history, with Debby Ryan most likely haunted by her hilariously self-important comments about her big meeting with Disney ahead of her 2011 sitcom Jessie. And no, you're not alone if you have absolutely no idea what that show is. Speaking about Jessie on a red carpet, Debby told a reporter: 'My one thing was, I went into the Disney Channel building and I sat down with the president of Disney Channel and I said: 'I want to make history.'' Putting one hand on her hip and smiling proudly to herself, Debby added: 'And that's what this is.'
And speaking of former child stars, Miranda Cosgrove has been open about the viral fallout from her 2020 appearance on Whitney Cummings' Good For You podcast, where she impishly confessed to the risque act of swearing. Between giggles, Miranda proudly told Whitney: 'I actually do cuss a little,' and when asked what her favorite curse word is, Miranda embraced her inner daredevil as she cautiously admitted: 'Probably fuck.' At this point, uncontrollable, borderline-deranged laughter is audible, which was incorrectly attributed to Miranda for years — and arguably made the whole thing all the more embarrassing for her.
Setting the record straight in 2022, Miranda said that it was actually Whitney's laughter that has been haunting her public image for years, telling Entertainment Tonight: 'I keep texting her, like: 'You framed me. You know, all of TikTok is making fun of me!'"
You can the clip, and hear Whitney's laugh for yourself, below:
Next up is Kendall Jenner's straight-up incomprehensible response to being asked what her spirit animal is during Vogue's 73 Questions in 2016:
Erm.. Whatever you say, Kenny!
Watch below:
Kendall isn't the only celeb whose apparent attempt to be deep massively backfired, with Noah Centineo seemingly having no idea where his People's Choice Awards acceptance speech was going when he took to the stage in 2019. With his voice cracking as he took on an incredibly serious and sombre tone, Noah told the crowd: 'And before I go, I just want to say: It matters not… What you've done… But what you do with what you've done... For others.' So true, Noah!
You might need to watch the clip in question to really feel the awkwardness of it all:
And sorry, Tyler Oakley, but your absolutely mortifying acceptance speech at the 2016 Webby Awards has not been forgotten! The American YouTuber coyly giggled as he took to the stage before proudly saying: "Monkey covering eyes emoji... Thanks!" complete with actions. Oh, it's painful.
Watch below, if you think you're strong enough:
I don't know about Olivia Wilde, but I am personally still haunted by Shia LaBeouf dropping the receipts that proved Olivia's recollection of what happened during Don't Worry Darling production wasn't entirely accurate. For reference, amid widespread speculation that director Olivia was beefing with her lead actor Florence Pugh, Olivia publicly insisted she'd replaced Shia in the movie for Florence's comfort... Then Shia released a video he'd received from Olivia singing his name before basically begging him to reconsider dropping out of the production — and condescendingly referring to Florence as 'Miss. Flo..." Yikes!
I'm sure you know what video I am talking about, but you can watch it here if you need reminding!
And remember that time a random elderly lady accidentally roasted Dua Lipa to her face? For context, Dua was interviewing a group of old people who were totally oblivious to her fame for Jimmy Kimmel Live. As one of the interviews drew to an end, Dua enthusiastically asked the woman: 'Do you think you could, like, look straight into the webcam and say: 'Dua Lipa is the greatest pop star in history' for me, please?' But the woman point blank refused, dryly telling the Grammy-winning star: 'I'd never say that.' Better luck next time, Dua.
You can watch the clip below:
Normani's fandom nightmare is even more embarrassing, with the former Fifth Harmony star being accused of running her own fan account, Normani Nation, just last year… And I'm literally grimacing at the memory of it. Basically, in February 2024, Normani Nation posted a screenshot of the singer's Instagram account, which had been totally wiped of all posts as well as her profile picture, to X. 'WHAT IS HAPPENING' the fan account asked, but other users quickly noticed that the screenshot looked suspiciously like Normani's own Instagram backend, and had the kinda view that only the account owner would see. Why would Normani's fans have access to the 'Edit Profile' button, for example?
The tweet was swiftly deleted, and to make matters worse, when Normani was asked if she was behind the account in a subsequent interview with the Cut, her publicist reportedly stepped in and requested to skip the question. Ahhh!
On a similar note, Chloe and Halle Bailey told on themselves when they accidentally joined their own livestream during their Ungodly Hour era of 2020. The sisters looked mortified and seriously uncomfortable when they realized that they'd given the game away by revealing that their 'live' Zoom performance was actually prerecorded. Dressed in the exact same clothes as the recording, Halle looked as though her soul had left her body as she awkwardly stared into the camera with a sheepish smile frozen on her face.
Click here to watch the clip!
I also need to remind you all of the mic-drop response that podcaster Tana Mongeau had for TikTok comic Matt Rife when he opened up about the 'humbling epiphany' he'd recently had about his haters. Speaking on Cancelled with Tana Mongeau, Matt said: 'So many fucking people hate me for really no reason and it made me realize that people only hate somebody they're jealous of.' And while Matt was seemingly busy mentally patting himself on the back for this revelation, Tana bluntly asked him: 'Do you think people who hate Osama bin Laden are just jealous of him?'
And while we're on the subject of Matt Rife, here's an honorary mention of that time a plastic surgeon made a video joking about 'creating the greatest jawline ever seen' on an unnamed celebrity and, for some inexplicable reason, Matt responded… With a seriously cringeworthy, can't-take-a-joke comment at that.
I'll always be wondering what exactly was going through Whoopi Goldberg's mind when she asked her The View co-host Alyssa Farah Griffin if she was pregnant live on TV — and in the middle of a sentence that was about something totally unrelated. Like, they were literally discussing Mitt Romney. Needless to say, Alyssa was visibly taken aback by the sudden pivot in conversation, and looked totally mortified as she confirmed she wasn't pregnant. Clearly flustered, Alyssa exclaimed: 'Why, do I look pregnant??' To which nonchalant Whoopi replied: 'I just got a vibe, I'm so sorry.' Eek.
Finally, sorry, Zac Efron, but I am going to remind everybody of that time you dropped a condom on the red carpet, in front of the world's media and a whole bunch of fans, at none other than The Lorax movie premiere back in 2012.
Needless to say, Zac looked super embarrassed in the moment, and even needed to take a minute to compose himself as he struggled to fight back laughter after he'd quickly put the condom back in his pocket. You can watch the whole thing here!
Congratulations if you managed to make it all the way through this list without curling up into yourself!
As always, let me know your thoughts — and favorite embarrassing celebrity moments — in the comments below. And if you missed it, check out part one of this round-up here!