There are moments from entertainment, fashion, and art that become truly iconic, glowing brighter with every retelling. And then there are pop culture moments famous for very different reasons, reminding us the spotlight can be slippery. Not every televised second turns into gold, and some live on as wonderfully awkward stories kept alive online.
When someone asked people to share cringeworthy celebrity experiences, the responses poured in fast and honest. They remembered stars accepting awards they never won, toasts that went off the rails, and jokes that were stretched a beat too long. The range was wide, yet the feeling was the same, pure secondhand embarrassment.
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Four Seasons Total Landscaping still makes me cackle like once a month.
I have a T-shirt from them that says “Lawn Order - make America rake again.” 🤣🤣🤣
Not the only one cracking up, OP. Late Night with Seth Meyers mentioned that Trump was set to take a photo with U.S. attorneys today at the White House, but, as usual, Giuliani misunderstood. Then a photo of Giuliani standing in front of a White Castle mocked up by the graphics dept. came on the screen.
I hadn't thought about that for quite a while, so thanks a bunch for the reminder. I really needed that in view of all that's happened in the last year.
And will be happening for the foreseeable future.
Load More Replies...The fact that they still went ahead. I mean someone must arrive at the site way ahead, and question - is this the right place? When obviously it wasn't. So just pack up quietly and disappear into thin air. Later make proper press conference, make sure is at decent place, say something about technical issues that hampered previous one.
We can thank baby Jesus for calling him home. Good riddance.
Load More Replies...And now we're stuck with his racist wife who's carrying on his sick, bigoted message.
"I don't agree with Charlie Kirk being gunned down in a school shooting. But he did."
My donut just went down the wrong pipe! 😆 Yeah, it’s funny, but even Kirk couldn’t disagree with that. 🤣
Load More Replies...Never forget that he said it would be worth it for some people to die in shootings each year if it meant the second amendment could endure
When Beyoncé dressed up as Toni Braxton for Halloween and Kris Jenner thought she dressed up as her.
With all the horrendous natural disasters California has experienced these past couple of years, and the Kardashian/Jenner clan continues unscathed. Proof there is no god.
As a lifelong Southern Californian, I consider the Kardashians/Jenners to BE one of California's horrendous natural disasters :/ Except most of them are pretty UNnatural with all the plastic surgery, but you know what I mean XD
Load More Replies...Talking about embarrassing things, there’s also no shortage of them among fashion trends. Hammer pants are a perfect example — iconic, yet at the same time very specific to the early ’90s. They were oversized, and because of that, people moved in them like dancers wearing friendly parachutes. Pop stars made them look rebellious; meanwhile, regular folks just looked like they were smuggling sofa cushions. The style was comfortable, but eventually the world realized comfort and cool don’t always share an address. Fashion often learns through baggy trial and error.
Katy Perry kissing the ground after going into "space" for less than 20 minutes as if she went on some life-ending mission😭😭
RobbieRedding:
Reminds me of when Jeff Bezos blew off William Shatner while he having a very deep moment.
It’s equal parts cringe and sadness.
Did you know? Katy Perry, the world famous astronaut, is also a singer and has released multiple albums?
And yet not one person pushed her face into the ground. What's wrong with bystanders nowadays?
It's just ridiculous that people call her an astronaut. According to that logic I am a train driver, because I travel by train.
Jeff Bezos blew off William Shatner? How come this wasn't in the news?
You gotta watch it, it made me want to punch bezos in the throat
Load More Replies...And it's debatable as to whether she went to "space" at all, as it depends which definition of "space" you take. LOL
She takes up space. That surely must account for something, right?
Load More Replies...To be fair, if I had to get onboard Bezos' penile enhancement, I'd probably be kissing the ground after getting off in one piece too. That and speaking Norwegian (meaning vomiting) in the bushes
Paris Hilton kissing a (not pregnant) woman’s belly.
According to IMDb and The Daily Mail (both incredibly reliable sources for all your news) claim the woman was pregnant. Whether true or not, it's pretty bizarre.
It’s NEVER in the history of time been safe to assume a fat woman is fat because she’s pregnant, and yet some people hafta learn by assuming pregnancy and then getting a wheelbarrowful of embarrassment and humiliation. But to learn by PLACING YOUR LIPS ON SOMEONE’S BELLY?! 😳🥵 I winced so hard I got a kink in my neck for 48 hours, and this entry just brought that all back. Holy mackerel!
Load More Replies...J Lo’s, “I like taking my hair out like this. It reminds me like, when I was 16 in the Bronx running up and down the block. Crazy little girl who used to f---ing be wild and no limits, all dreams.”
natttynoo:
Haha then she visited her old bronx home and the guy didn’t know who she was LOL
The video of her crying when she found out she wasn't nominated for an Oscar for Hustle. It's one thing to be disappointed, but she seemed to think she was owed a nomination.
I loved when she felt she needed to try and show Shakira how to dance lol the attitude and entitlement is wild .Shakira..like really?!
Load More Replies...Light-up sneakers arrived next, and suddenly, feet turned into mobile discos. The first step flashed like a tiny thunderstorm under your ankles, so naturally, kids stomped every hallway just to show off the fireworks. Even though adults tried to borrow the glow, the novelty faded fast, because in truth, glowing shoes rarely match serious outfits. Still, the trend taught fashion an important lesson about subtlety. Footwear can shout; however, memories shout louder.
“Keep my wife’s name, out of your F**KIN’ MOUTH!!”
Yeah, this moment is definitely up there! Especially when he still won the Oscar that same night!
I remember Will laughing hysterically at first. Then presumably he got his orders.
I'm glad someone else noticed that and remembers
Load More Replies...Even worse was the standing ovation he got when he won and then the pathetic non-apology.
And then the Oscars let him stay, and then win the award. Tbh he's doing enough to keep his career in the dumps so that's fine with me.
OMG he is a grown man who is responsible for his own actions. Can we stop blaming wives and mothers for everything a man does? Jesus!
Load More Replies...This outrageous behavior was the last straw for me. Up until then, I kind of liked Smith, but now I refuse to watch anything he's in. The Freak Family doesn't need our attention anymore.
Why he felt the need to defend the "honor" of a woman who proudly described her vulvar plastic surgery and how great it looks down there now to the entire world, I'll never understand. Rich people can be trashy, too.
He didn’t seem to feel the need at all; he was enjoying the bit (it wasn’t unkind!) and was laughing and having a good time until Jada shot him daggers, and then suddenly, it was entirely inappropriate and аssault -worthy. You don’t hafta believe me; go watch the video again and you’ll see it. As an aside, I don’t understand the whole “Keep my name out your mouth” nonsense; if no one ever mentioned a celebrity’s name, they wouldn’t BE celebrities. And we’ve a Panda who demands the same nonsense (you know the one: She’s 60, in the UK, calls people “vile scum” for even the most minor of infractions, and has worked in every profession known to man) as if she’s so important. I don’t get it: They feel we should only “talk” about them by … playing Charades? Using smoke signals? Oh! We could type their names on our phones then hold ‘em up to show someone who we’re thinking of? I vote we NOT speak of those people at all, ever, so they’ll slide back into the obscurity from which they came! Oooh; I’m okay with that!
Load More Replies...Not at all. It's definitely bad to laugh at the joke and then a*****t the person who said it.
Load More Replies...Ryan Seacrest trying to high five a blind man
Okay, honest mistake to make in the moment. I once accidentally pointed towards a product and said "here" before remembering that the customer I helped was blind.
Eeeehhh. 'Blind' is a very catch all term. People can be considered/registered blind and still have some usable vision. This one isn't meant maliciously.
Imagine video during COVID will forever be the answer.
let-them-eat-as:
My workplace tried to recreate it and everyone promptly ignored the email collectively.
ClubberLang5:
2020 is gonna be such an insane year to try to teach about in the history books lmao.
ismaithliomsicin:
I still have never watched the whole video I could not handle the cringe.
Well, unlike y'all, I appreciated the off-key efforts these celebrities made during isolation while surrounded by their excessive possessions and comfortably wrapped in their wealth. True heroes who related to us all.
Now that's a level of sarcasm I can appreciate. 🤣
Load More Replies...It was the look on her face that got me. Like "This must be so amazing for all you little people that us stars are singing for you. You're welcome!" I was also horrified that Kristin Wiig was in that. I love her, but man I thought she had more sense.
I've never watched it became I was at work when this came out.
Ditto. I do consider myself fortunate for that, though, in that I’d been bored out of my tiny brain otherwise.
Load More Replies...Shutter shades and neon accessories ruled the mid-2000s, and as a result, parties looked like highlighters attacked wardrobes. Plastic slats across the eyes made vision optional, and yet confidence mandatory. Although magazines called it edgy, morning photos told a different story, so eventually the internet built a museum of cringe just for them. Pop culture loved the brightness, while at the same time, reality loved the comedy. Style and embarrassment often dance together.
Arizona Cardinals QB Kyler Murray confusing Britney Griner for his former wide receiver Larry Fitzgerald
Kelly Rowland texting Nelly via Microsoft Excel and getting mad because he didn't text her back.
I've used MS Excel for years and never knew you could use it for texting. Wow, MS, this is taking bookkeeping to a whole new level. Seriously, just started watching a confusing YT tutorial and there are so many steps required, it's just easier to send texts through the normal channels.
That is a Power point you've delivered there Riley
Load More Replies...Chris D’Elia, the moment he realized on camera that snapchats can be recorded and that the minors he tried to groom could expose him. A wonderful internet moment.
I was attracted to him until I found out about this tidbit. May Karma find this creep again.
Frosted tips and spiky hair became the hedgehog era for young men, and because every barber owned extra gel, the look spread like wild glue. While boy bands celebrated the peaks, parents mourned perfectly decent hair. The style said carefree, yet the mirror whispered caution. Eventually, the frosting washed out and the spikes relaxed, so in the end, time acted as the strictest stylist. Fashion trims even the bravest scalps.
This is one of my favorites because It’s something I would do and i’m glad it wasn’t me. Lol
I'm answering like this next time someone asks me what my favorite dish is. I actually do HAVE a favorite dish, it's a small plate with a black cat painted on it...
My favourite is a large plate with deep sides. It says "Pasta" inside, in case there was any doubt, and it is where I put my linguine in between pan and tummy. 😺
Load More Replies...Adele Dazeem 2014 moment.
John Travolta was supposed to introduce singer Idina Menzel and instead totally got her name wrong and said ' Adele Dazeem '. The following year at the next Oscar's, Idina poked fun by introducing John Travolta as Glom Gazingo.
Load More Replies...I guess you actually have to watch the Oscars regularly to get most of these
This is the only Oscars-related entry on the page, if memory serves. You need to pay attention to pop culture news and the zeitgeist to get most of these.
Load More Replies...La la Land being mistakenly named Best Picture instead of Moonlight was legit crazy and made me wish I lived under a glacier in Antarctica to avoid the second hand embarrassment.
Anyone except those in the room felt embarrassed should have their lives re-evaluated.
There was a mistake with the envelope at the Oscars one year.
Load More Replies...Extremely tight skinny jeans stepped into the spotlight, and from that moment, legs filed for breathing permits. They looked sleek, yet didn’t do much for health or circulation, so gradually many people discovered the value of denim that allows oxygen. Even though mirrors applauded, bus seats protested, and finally comfort packed its bags. Fashion sometimes wins, but eventually knees demand a recount.
Gwen Stefanis cultural appropriation era Just to turn into a MAGA/ Ultra Christian conservative 💀
Good to see she is helping the environment by taking the plastic out of the ocean and putting it in her face
Back when she started her "Harajuku era", I read some interviews and she claimed that she liked their fashion and was inspired by it. I mean, it's fine. I just don't understand what possesed her when she said she was Japanese?
I never saw this but was immediately reminded of "Three Little Maids from School Are We" Gilbert and Sullivan, The Mikado, for you youngsters.
The past 35 years have been Gwen Stefani’s cultural appropriation era.
That's not even remotely what happened here. She didn't "just" wear a kimono.
Load More Replies...When they presented Michael Jackson with a birthday cake at the 2002 VMAs and he thought they were giving him an "Artist of the Millenium award" and made a very awkward speech. Britney's outfit here is also embarrassing.
When Jennifer tried to create her own challenges, like the throw your jewelry in the ocean challenge. 🤣
Throw your ex's jewelry in the nearest body of water, that's my challenge
Low-rise everything dipped so far, and as a result, waists felt abandoned by designers. Visible thongs and extreme midriffs became uninvited guests, yet at the same time, red carpets treated them like royalty. Gravity tested the trend, so eventually humility arrived right on schedule. The style depended on good balance, while common sense depended on higher waistlines. Fashion discovers limits one bend at a time.
Drake presenting the award to Rihanna and expressing his love while she stood on stage, dying.
MagnetoWasRight24:
Back then I thought Drake was gay and this was him doing too much to hide it. Turns out he's just corny and weird.
Drake likes texting inappropriate messages to under age girls.
Rihanna is so far out of his league, and besides, isn't she way too old for his tastes? Could ask Kendrick, I suppose.
Probably Fergie when she sang the national anthem that one time lol
DontCryYourExIsUgly:
The players' reactions were so funny to me.
She thought she nailed it, which makes it even funnier! Let's play some basketball! 🤣🤣🤣
Cringe? Heck, when I need cheering up, good ole Fergie butchering the anthem while the players, Chance, and Jimmy Kimmel were laughing is good medicine. Between Fergie and Trump, American flags aren't safe from their seduction.
AnnaLynne McCords “if I was Putin’s mama” poem 😭
As long as you're googling poems check out "The Perfect High" by Shel Silverstein.
Load More Replies...I'm not really a fan of either of them, but man I felt for Taylor as I watched her get The Ick in real time when Travis Kelce started singing Viva Las Vegas after they won the Superbowl.
I don't think I have ever watched a football game. If they played the superbowl on my lawn I wouldn't watch it. All that aside, that was possibly the biggest win of that guy's life, so if he did something stupid I would be able to overlook it in that instance.
I just watched the vid and since the mic wasn’t turned on, we haven’t any way of knowing WHAT the hell he said. For all I know, he finally stepped out of the closet. ¯\_(ツ)_/¯ I’m with you; doing something boneheaded or silly out of excitement is okay with me. (I do NOT, however, give the same pass to MMA fighters who upon winning behave as if they’ve solved world hunger and climate change and defeated death, sometimes attributing it all to god (who I can’t imagine watches MMA) as it is so absurdly, embarrassingly, over-the-top insane that my second-hand embarrassment and shame is near fatal. A Super Bowl win? 👍🏻 Beating the 14th ranked welterweight in the promotion? Not even close.)
Load More Replies...Bedazzled and rhinestone clothing sparkled through the early 2000s, and because of that, shirts looked like disco balls taking naps. The shine felt glamorous; however, washing machines became battlefield generals, so in the end, the appeal dulled faster than the gems did. Pop culture kept the glitter alive, while everyday life preferred eyesight. Still, these bright mistakes remain reminders that style is a long, sparkling experiment.
Hilaria Baldwin in the winter of 2020 trying to explain why she has been cosplaying a Spanish woman when shes a fully white person from Boston.
She's so fake. Funny, I think her hubs was shocked & embarrassed when all that broke out. But then he has enough baggage of his own as well
they are European and yes, they are Caucasian white people. It's a nationality not a race.
Load More Replies...Spanish people are considered white. Why do Americans think they aren't?
OK hear me out If this was true, wouldn't it be a number one tourist spot?? Plus all those cats pushing things off the edge .
Reason 967 why the earth can't be flat, because big companies would monetise it, there would be a Starbucks overlooking the edge immediately.
Load More Replies...Frankly, if they were, they deserve to have their money wasted.
Load More Replies...I volunteer to accept the money to be your checker. Should take 1 entire day, contingent on the weather being sunny
When Miguel was performing at some awards show and tried to jump over some people and kicked them in the head after he was told not to try to jump over people because he might kick them in the head.
When Lindsay Lohan tried to kidnap a child
Yeah, she genuinely had a real disconnect and actually thought she was helping... a whole family just trying to eat their dinner and her assuming the child needed help, knowing nothing about them was crazy. It was painful to watch... i felt bad for her 'issues' and that family. The whole thing was a mess.
Well, whether it’s fashion choices or celebrity mishaps, certain moments carry that sharp sting of secondhand embarrassment. Loud outfits, shaky award speeches, and interviews that drift into awkward silence all create the same restless urge to hide under a table. What are your thoughts? Which one of these moments made you want to crawl under a table the fastest?
Jerry Seinfeld rejecting a hug from Kesha. I like to watch bc however awkward i may feel, i will never reach this level of awkward.
Jerry Seinfield has done worse like dating that school girl.
He said it was only that one time. 🤣 I did feel bad for him when I saw this video, although overall I think his comedy aged like milk.
Load More Replies...Most modern "artists" wouldn't. It's the worst thing that has happened to music production, I think.
Load More Replies...Lil Mama going on stage with Jay Z and Alicia Keys is literally painful to watch
She hasn't had a hit single since this "hack". Taika Waititi is still with her, even if her fans aren't.
This girl from TikTok who tweeted this about a # that was made for Charli XCX when Sophie passed.
Like girl 😭
And can't even bother to go find out who they are because 90% of the time I still can't figure out how they became so famous. So and so was on ( some reality TV show I never heard of ) and then did ( some stupid influencer thing ) .
Load More Replies...Don't ask...it'll only encourage people to give wrong answers.
Load More Replies...Honestly, we've all been super tired and not made the same connections in our head that might be obvious to others.
This whole speech, both for his random intensity and Winona's utter bewilderment.
In the words of Ricky Gervais: "come up, get your little award, thank your agent, thank your God and f**k off."
The only portions of the Globe Awards I've watched are the bits with Gervais.
Load More Replies...I have no idea who this is or what the award is for. A little bit of detail wouldn't go amiss.
It won't help you considering these are actors from the biggest show in the last 10 years and you "have no idea who this is".
Load More Replies...theglowcloud8:
Makes sense. Everything I have ever heard about Nikki Blonsky has been about how awful she is.
I would screenshot her response but I deleted Twitter years ago, still it's a perfect burn
This is actually hilarious, even having no idea who blonsky is the response she got cracks me up
Wikipedia: In July 2008, Blonsky and her parents were involved in an aggravated confrontation with the family of Bianca Golden, a former contestant on America's Next Top Model, at the Providenciales International Airport in Turks and Caicos over saved seats in the airport departure lounge. Golden and Blonsky were charged with actual bodily harm and Blonsky's father with grievous bodily harm, a felony. That December, the charges against Blonsky and Golden were dropped. It has been alleged by Golden that the altercation was racially motivated and involved racist remarks,[32] but this is vehemently denied by Blonsky, who remarked in an Instagram story: "I am deeply saddened and hurt to hear I have been wrongly accused of ever having anything other than love in my heart for someone of a different race, when that couldn't be further from the truth".
Sücks when you have to do an internet search of your kids to wish them happy birthday.
The oof heard 'round the world. Yikes to the max on "Mia Farrow and her black children"
Hasbulla is a Russian social media personality with dwarfism, who Tyson scooped up like a baby not realizing he was 26yo.
Usher thinking he was going to be in the middle of this “We Are The Champions” video
This A-Rod photo shoot.
It's either a mirror or he's kissing his identical twin brother.
Load More Replies...Small cringe but Dua lipa trying to pose with Billie Eilish and getting ignored
Emilia Pérez composer singing in her Oscar's acceptance speech
I dont know who the bald guy is, but i dont think its the speech he's paying attention to.
This entire thing should have been a private text message. Actually I feel like 90% of celebrity twitter drama should have just been a text message. I need people to get a group chat.
Apparently Jensen Ackles was working on a Supernatural prequel, with no plans to involve/include Jared. After learning about the planned program on social media, he sent a tweet to Jensen expressing his disappointment at having to find out about it that way. The tweet above, which he later deleted, was sent to Supernatural executive producer Robbie Thomson after Jared learned that he (Robbie) was going to be a writer on the show.
Load More Replies...When Justin posted this story and Selena’s Coachella outfit was in his history tabs. The most embarrassing because it’s so relatable
When Tom Hiddleston was playing hide the sausage with Taylor Swift. He wore that vest.
Load More Replies...Why was the media shocked that two hot people of an age slammed? Why was anyone?
Because it was very public and looked forced, too much even for Taylor
Load More Replies...Yep. You know the song Getaway Car? She couldn’t get rid of Calvin Harris so she, by agreement, took up with Tom Huddleston, very VERY publicly. Harris was running after them and she was screaming go go Go but A circus ain’t a love story and they were both sorry.
Er, Tom HIddleston. Tom Huddlestone is an English footballer.
Load More Replies...Katy Perry's promotion of Witness and everything that happened there was...yeah.
This guy, whose marriage was TOTALLY FINE
Dominic West. British actor. He was pictured looking very cosy with Lily James, so he and his wife released a statement saying their marriage was fine and neither confirming or denying the rumours.
Load More Replies...Actor in alot of films, like The Crown, and tv series The Wire, has a reputation of cheating.
“Shout-out to his family”
Thought that was H from Steps and that he must be doing alright for himself if he's performing in New York.
Millie Bobby Brown saying “the dirtier, the better” with that expression on her face
If your comment section is rife with comments about how shittily pulled together your listicles are and it's multiple people with the same, valid, complaint...maybe, just maybe, take the f*****g advise and make changes. We, as your readers, cannot understand w*f you're talking about. There is a constant lack of context among many, many other glaring problems, but all BP cares about is cleaning up no no words and pandering to their click bait advertisers.
Is it just me or does she look like Wallace from Wallace and Gromit here? Lol
I don't understand the embarrassment to the celebrity here. Random person asks for money, no context, in a tweet. Responding to each and every financial request would be foolish, right? It is strange to tweet for help. IDK.
Does this count? Halsey accidentally calling for the World Trade Center to collapse.
He dressed in drag and lip synched Rihanna at her then finished in a dead drop on a rainy stage. Seriously look up his lip sync battle if you haven't. It was absolutely him being okay with this idea.
I've had this video favourited for years and never get tired of it. He is a fabulous dancer (I know he trained as one, but still).
Load More Replies...Judge if u must but seemed to have worked out really well for them. All these years and a ring later, they still fawn over eachother like that 💜
Note: this post originally had 52 images. It’s been shortened to the top 50 images based on user votes.
Either this list is too US-Centric, I am incredibly out of touch or I'm just too old.I have no idea about most of these stories or any idea who the people are. I don't care enough about any of them to Google.
I'm American and while I vaguely recognize most of the names, I have no idea what most of these are referring to.
Load More Replies...What about Oprah trying to wipe off Drew Brees’ birthmark thinking it was a lipstick print.
Oh come on - No mention of the Rachel Zegler interview for "Snow White" or Jennifer Lawrence saying that she was the first female action-hero character on stream in "The Hungergames"? (Because s***w Ellen Ripley, right?)
What even was this? I guess AI has yet to be taught about context.
Literally no idea what's going on, who are those people and why they are mentioned.
Either this list is too US-Centric, I am incredibly out of touch or I'm just too old.I have no idea about most of these stories or any idea who the people are. I don't care enough about any of them to Google.
I'm American and while I vaguely recognize most of the names, I have no idea what most of these are referring to.
Load More Replies...What about Oprah trying to wipe off Drew Brees’ birthmark thinking it was a lipstick print.
Oh come on - No mention of the Rachel Zegler interview for "Snow White" or Jennifer Lawrence saying that she was the first female action-hero character on stream in "The Hungergames"? (Because s***w Ellen Ripley, right?)
What even was this? I guess AI has yet to be taught about context.
Literally no idea what's going on, who are those people and why they are mentioned.
