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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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#1
Four Seasons Total Landscaping still makes me cackle like once a month.
emorinelli49 15 hours ago
I have a T-shirt from them that says “Lawn Order - make America rake again.” 🤣🤣🤣
Riley Quinn 15 hours ago
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.
Lotekguy 11 hours ago
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.
General Anaesthesia 6 hours ago
And will be happening for the foreseeable future.
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RELATED:
#2
MontanaMariner 12 hours ago
We can thank baby Jesus for calling him home. Good riddance.
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Riley Quinn 14 hours ago
And now we're stuck with his racist wife who's carrying on his sick, bigoted message.
PenguinEmp 8 hours ago
Click here to order now. It's what Charlie wanted.
Load More Replies... #3
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.
Nathaniel He/Him Cis-Het 17 hours ago
Did you know? Katy Perry, the world famous astronaut, is also a singer and has released multiple albums?
Riley Quinn 15 hours ago
And yet not one person pushed her face into the ground. What's wrong with bystanders nowadays?
Did I say that out loud? 10 hours ago
Jeff Bezos blew off William Shatner? How come this wasn't in the news?
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.
#4
When Beyoncé dressed up as Toni Braxton for Halloween and Kris Jenner thought she dressed up as her.
Riley Quinn 15 hours ago
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.
#5
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
Norfolk and good 16 hours ago
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.
Partypants 15 hours ago
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... #6
Paris Hilton kissing a (not pregnant) woman’s belly.
Riley Quinn 15 hours ago
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.
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.
#7
“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!
Nathaniel He/Him Cis-Het 17 hours ago
I remember Will laughing hysterically at first. Then presumably he got his orders.
Phantom Phoenix 9 hours ago
I'm glad someone else noticed that and remembers
Load More Replies... Norfolk and good 17 hours ago
Even worse was the standing ovation he got when he won and then the pathetic non-apology.
Sue User 2 hours ago
Can't decide to pity him or if he is equally at fault.
Load More Replies... PenguinEmp 15 hours ago
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.
Riley Quinn 15 hours ago
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.
Earthquake903 8 hours ago
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.
Pollywog 10 hours ago
Not at all. It's definitely bad to laugh at the joke and then a*****t the person who said it.
Load More Replies... #8
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.
Riley Quinn 15 hours ago
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.
Spencer's slave no longer 7 hours ago
I've never watched it became I was at work when this came out.
Jaya 14 hours ago
Covid was stressful for everyone, including people who were rich and didn't have to fear getting in financial trouble. You couldn't socialize, you had to worry about your elderly loved ones getting infected and dying. Those things were hard for everyone, even if you have a nice mansion it's still gonna súck. So I don't blame them at all.
#9
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.
QueenKittyCat 24 minutes ago
I was attracted to him until I found out about this tidbit. May Karma find this creep again.
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.
#10
Arizona Cardinals QB Kyler Murray confusing Britney Griner for his former wide receiver Larry Fitzgerald
#11
Ryan Seacrest trying to high five a blind man
TotallyNOTAFox 30 minutes ago
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.
#12
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.
Bec 13 hours ago
There was a mistake with the envelope at the Oscars one year.
Load More Replies...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.
#13
Kelly Rowland texting Nelly via Microsoft Excel and getting mad because he didn't text her back.
Riley Quinn 15 hours ago
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.
Phantom Phoenix 8 hours ago
That is a Power point you've delivered there Riley
Load More Replies... #14
Gwen Stefanis cultural appropriation era Just to turn into a MAGA/ Ultra Christian conservative 💀
Barbara Wilcock 14 hours ago
Good to see she is helping the environment by taking the plastic out of the ocean and putting it in her face
#15
Adele Dazeem 2014 moment.
T Barth 10 hours ago
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... Earthquake903 8 hours ago
I guess you actually have to watch the Oscars regularly to get most of these
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.
#16
When Jennifer tried to create her own challenges, like the throw your jewelry in the ocean challenge. 🤣
Sally Moen 12 hours ago
Throw your ex's jewelry in the nearest body of water, that's my challenge
#17
This is one of my favorites because It’s something I would do and i’m glad it wasn’t me. Lol
#18
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.
meeeeeeeeeeee 3 hours ago
Spanish people are considered white. Why do Americans think they aren't?
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.
#19
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.
#20
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.
Nathaniel He/Him Cis-Het 17 hours ago
Drake likes texting inappropriate messages to under age girls.
Colt Winkler 5 hours ago
i still dont know about this, i really feel like hed be in jail by now if it was really the case. but maybe im naive
Load More Replies... Riley Quinn 14 hours ago
Rihanna is so far out of his league, and besides, isn't she way too old for his tastes? Could ask Kendrick, I suppose.
#21
Probably Fergie when she sang the national anthem that one time lol
DontCryYourExIsUgly:
The players' reactions were so funny to me.
Norfolk and good 16 hours ago (edited)
She thought she nailed it, which makes it even funnier! Let's play some basketball! 🤣🤣🤣
Riley Quinn 14 hours ago
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.
#22
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.
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.
#23
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.
#24
This girl from TikTok who tweeted this about a # that was made for Charli XCX when Sophie passed.
Like girl 😭
Gordon 9 hours ago
Don't ask...it'll only encourage people to give wrong answers.
Load More Replies... Sue User 2 hours ago
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... #25
When Lindsay Lohan tried to kidnap a child
Lavender Myst 16 hours ago
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.
#26
AnnaLynne McCords “if I was Putin’s mama” poem 😭
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?
#27
Emilu 10 hours ago
Frankly, if they were, they deserve to have their money wasted.
Load More Replies... Sally Moen 12 hours ago
I volunteer to accept the money to be your checker. Should take 1 entire day, contingent on the weather being sunny
#28
theglowcloud8:
Makes sense. Everything I have ever heard about Nikki Blonsky has been about how awful she is.
Sally Moen 12 hours ago
I would screenshot her response but I deleted Twitter years ago, still it's a perfect burn
Lynchamigsakta 1 hour ago
This is actually hilarious, even having no idea who blonsky is the response she got cracks me up
Riley Quinn 14 hours ago
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".
#29
Riley Quinn 14 hours ago
She hasn't had a hit single since this "hack". Taika Waititi is still with her, even if her fans aren't.
#30
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.
Nathaniel He/Him Cis-Het 16 hours ago (edited)
Jerry Seinfield has done worse like dating that school girl.
Austzn 49 minutes ago (edited)
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.
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#31
Lil Mama going on stage with Jay Z and Alicia Keys is literally painful to watch
#32
Riley Quinn 14 hours ago (edited)
Sücks when you have to do an internet search of your kids to wish them happy birthday.
*raspberry sound 15 minutes ago
The oof heard 'round the world. Yikes to the max on "Mia Farrow and her black children"
#33
Riley Quinn 14 hours ago
Hasbulla is a Russian social media personality with dwarfism, who Tyson scooped up like a baby not realizing he was 26yo.
#34
Lavender Myst 16 hours ago
Honestly, we've all been super tired and not made the same connections in our head that might be obvious to others.
#35
Usher thinking he was going to be in the middle of this “We Are The Champions” video
#36
Katy Perry's promotion of Witness and everything that happened there was...yeah.
#37
This whole speech, both for his random intensity and Winona's utter bewilderment.
Norfolk and good 16 hours ago (edited)
In the words of Ricky Gervais: "come up, get your little award, thank your agent, thank your God and f**k off."
Riley Quinn 11 hours ago
The only portions of the Globe Awards I've watched are the bits with Gervais.
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#38
Nathaniel He/Him Cis-Het 16 hours ago
When Tom Hiddleston was playing hide the sausage with Taylor Swift. He wore that vest.
Load More Replies... Jesha 11 hours ago
Why was the media shocked that two hot people of an age slammed? Why was anyone?
Starbug 3 hours ago
Because it was very public and looked forced, too much even for Taylor
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emorinelli49 15 hours ago
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.
#39
Emilia Pérez composer singing in her Oscar's acceptance speech
Lavender Myst 16 hours ago (edited)
I dont know who the bald guy is, but i dont think its the speech he's paying attention to.
#40
This A-Rod photo shoot.
#41
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.
The Other Guest 2 hours ago
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.
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#42
Small cringe but Dua lipa trying to pose with Billie Eilish and getting ignored
#43
This guy, whose marriage was TOTALLY FINE
Norfolk and good 16 hours ago
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... Sally Moen 12 hours ago
Actor in alot of films, like The Crown, and tv series The Wire, has a reputation of cheating.
#44
When Justin posted this story and Selena’s Coachella outfit was in his history tabs. The most embarrassing because it’s so relatable
#45
“Shout-out to his family”
Norfolk and good 16 hours ago (edited)
Thought that was H from Steps and that he must be doing alright for himself if he's performing in New York.
#46
Sally Moen 12 hours ago
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.
#47
#48
Does this count? Halsey accidentally calling for the World Trade Center to collapse.
#49
Millie Bobby Brown saying “the dirtier, the better” with that expression on her face
*raspberry sound 6 minutes ago
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.
Pferdchen 1 hour ago
Well, as the world's best singers Lee Marvin and Clint Eastwood once sang: "The Best Things in Life are Dirty."
#50
Jesha 11 hours ago
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.
Emilu 3 hours ago
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).
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#51
Once again I feel I must direct people to Tom Hiddleston’s Michael Jackson impression.
#52
Obama trying to make a toast during the UK's national anthem.
Sally Moen 12 hours ago
Oh dear this really is terrible. There really isn't any President so awful...oh wait
Add New Image
What do you think ?
Panda McPandaface 16 hours ago
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.
Child of the Stars 14 hours ago
I'm American and while I vaguely recognize most of the names, I have no idea what most of these are referring to.
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Daniel Atkins 14 hours ago
What about Oprah trying to wipe off Drew Brees’ birthmark thinking it was a lipstick print.
liam newton-harding 3 hours ago
What even was this? I guess AI has yet to be taught about context.
TotallyNOTAFox 23 minutes ago (edited)
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?)
Panda McPandaface 16 hours ago
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.
Child of the Stars 14 hours ago
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... Daniel Atkins 14 hours ago
What about Oprah trying to wipe off Drew Brees’ birthmark thinking it was a lipstick print.
liam newton-harding 3 hours ago
What even was this? I guess AI has yet to be taught about context.
TotallyNOTAFox 23 minutes ago (edited)
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?)
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