52 Pop Culture Moments That Made People Cringe Hard

Jason Sargent Friday, January 9, 2026

- - 52 Pop Culture Moments That Made People Cringe Hard

Nikita ManotJanuary 10, 2026 at 12:01 AM

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.

“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!

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.

When Beyoncé dressed up as Toni Braxton for Halloween and Kris Jenner thought she dressed up as her.

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.

This girl from TikTok who tweeted this about a # that was made for Charli XCX when Sophie passed. Like girl 😭

Kelly Rowland texting Nelly via Microsoft Excel and getting mad because he didn't text her back.

Paris Hilton kissing a (not pregnant) woman’s belly.

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.

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.

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.

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

When Justin posted this story and Selena’s Coachella outfit was in his history tabs. The most embarrassing because it’s so relatable

#11

#12

AnnaLynne McCords “if I was Putin’s mama” poem 😭

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

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

#14

theglowcloud8:Makes sense. Everything I have ever heard about Nikki Blonsky has been about how awful she is.

#15

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.

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

Probably Fergie when she sang the national anthem that one time lolDontCryYourExIsUgly:The players' reactions were so funny to me.

#17

#18

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.

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

Ryan Seacrest trying to high five a blind man

#20

#21

Usher thinking he was going to be in the middle of this “We Are The Champions” video

#22

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

#24

When Jennifer tried to create her own challenges, like the throw your jewelry in the ocean challenge. 🤣

#25

This is one of my favorites because It’s something I would do and i’m glad it wasn’t me. Lol

#26

When Lindsay Lohan tried to kidnap a child

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

Does this count? Halsey accidentally calling for the World Trade Center to collapse.

#28

Arizona Cardinals QB Kyler Murray confusing Britney Griner for his former wide receiver Larry Fitzgerald

#29

#30

Katy Perry's promotion of Witness and everything that happened there was...yeah.

#31

#32

Gwen Stefanis cultural appropriation era Just to turn into a MAGA/ Ultra Christian conservative 💀

#33

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.

#34

Emilia Pérez composer singing in her Oscar's acceptance speech

#35

This whole speech, both for his random intensity and Winona's utter bewilderment.

#36

Once again I feel I must direct people to Tom Hiddleston’s Michael Jackson impression.

#37

This A-Rod photo shoot.

#38

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.

#39

#40

Millie Bobby Brown saying “the dirtier, the better” with that expression on her face

#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.

#42

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.

#43

“Shout-out to his family”

#44

Small cringe but Dua lipa trying to pose with Billie Eilish and getting ignored

#45

Lil Mama going on stage with Jay Z and Alicia Keys is literally painful to watch

#46

Obama trying to make a toast during the UK's national anthem.

#47

#48

Four Seasons Total Landscaping still makes me cackle like once a month.

#49

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.

#50

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.