Unforgettable Red Carpet Moments That’ll Make You Cringe

With awards season well underway, all eyes are going to be on the year’s hottest actors, singers, models, and even influencers. And while most of them will serve fashion wins and hilarious interviews, some will leave us feeling a little awkward.

But now is the perfect time to look back on all the awkward red carpet moments over the years. From uncomfortable interactions to fashion malfunctions, this list might make you cringe more than once.

That Time Kim K Got Flour Bombed.

During a perfume launch event in 2012, Kim Kardashian was attacked by a protester who covered her in flour. As if that wasn’t awkward enough to look at on its own, there’s also a good chance it was actually staged .

Bjork’s 2001 Swan Dress.

Love it or hate it, the dress was a moment. Not the most elegant take on a swan out there, but it at least got people talking.

Woody Harrelson’s 1997… Look.

Cosmopolitan wrote that the actor looked like an undertaker . To me, though, Harrelson seems more like a character out of some kind of steampunk alternate universe of The Matrix .

Hugh Grant Gets Handcuffed At A Movie Premier.

For the premier of his film Music and Lyrics in Amsterdam, Grant spent a lot of his red carpet time with a “fan” who’d handcuffed herself to him. According to Fox, the woman was from a prank show and ended up getting arrested .

Taylor Swift’s Grammy Red Carpet Interview From 2015.

Speaking with Nancy O’Dell from Entertainment Tonight , Taylor Swift was asked about her love life in a move that most thought was pretty inappropriate. But the singer dispelled any speculation by talking about going home to her cats, so there’s that.

Terrence Howard At The 2019 Emmy’s.

When asked about the possibility of retiring, Howard delivered a pretty…strange response. He might have been on to something about the universe, but then again, maybe not.

Amy Schumer Face Planted In Front Of Kim And Kanye In 2015.

While talking with Graham Norton on his show after the event, Amy Schumer explained that she fell in front of Kim and Kanye as a prank. And to be honest, the fact that she did it on purpose makes it a lot more awkward.

Emma Stone Shared An Awkward Moment With Damien Chazelle At The Golden Globes.

In 2016, Stone broke down her awkward moment, in which she hugged Chazelle, who was actually trying to hug his date. At least the actress could laugh about it later.

Sacha Baron Cohen Spilled Ashes All Over Ryan Seacrest In 2012.

During the 2012 Oscar red carpet, Cohen , dressed and in character for The Dictator , had an urn with fake ashes in it. He then proceeded to spill them all over an unsuspecting Ryan Seacrest , who was just trying to conduct an interview.

To Make Matters Worse, Jason Segal Got In The Way When They Were Cleaning It Up.

Because of course someone had to clean the ashes up. And of course Segal happened to be in the wrong place at the wrong time.

When Melanie Griffith Was Asked If She’d Seen ‘Fifty Shades Of Grey.’

Of course, Griffith hadn’t seen the sexually explicit movie, which starred her daughter, Dakota Johnson . To make things weirder, they got into a bit of an argument about whether Griffith should see the film.

Lil Uzi Vert’s Low Energy Interview At The 2018 Grammy’s.

Whether they were trolling or just not that into the interview questions, Lil Uzi Vert delivered some of the most low energy answers on the red carpet that night.

Pharrell Was Nominated For ‘Hidden Fences.’

Pharrell Williams was one of the talented artists behind the score of Hidden Figures , which was nominated at the 2017 Golden Globes. Jenna Bush Hager, who was interviewing the artist, talked about his nomination for Hidden Fences , a movie that doesn’t exist.

Hidden Figures and Fences were both nominated that night. Notably, both movies feature African American leads. Bush Hager did come out and apologize for the mix up later .

But She Wasn’t The Only One To Make That Mistake.

When announcing Octavia Spencer’s nomination for the same film, Michael Keaton introduced the film as Hidden Fences . Weird.

Giuliana Rancic ‘Dismissing’ Emilia Clarke On The Red Carpet.

Rancic was in the middle of interviewing Clarke , but then spotted Heidi Klum and decided the interview was over. “You can go now…” yeesh.

Will Smith Slapped A Reporter In 2012.

Years before the Oscar Slap that nearly ruined Will Smith’s career, Russian prankster Vitalii Sediuk tried to kiss the actor on a red carpet. Smith, who was not playing around, gave him a pretty light tap on the face.

The Same Prankster Violated America Ferrera.

Sediuk also appeared at the How to Train Your Dragon premier, and decided to try and crawl under Ferrera’s dress. He ultimately got escorted away.

Zac Efron Dropped A Condom.

Accidentally letting a condom fall out of your pocket wouldn’t be nearly as awkward if it happened anywhere but the red carpet for a children’s movie like The Lorax . Which is exactly where Efron was when it happened.

Kesha Wanted To Hug Jerry Seinfeld, But He Said ‘No Thanks.’

It was pretty clear that Seinfeld had no idea who Kesha was at the time. At least he let her down politely.

Bradley Cooper Hangs With A Clingy Fan At The Sag Awards.

Once again, Seduik struck the red carpet. In this case, he clung to Cooper’s leg (and had to be removed, of course).

He Went On To Do The Same Thing To Leonardo DiCaprio.

Seduik is nothing if not consistent. When hugging Leonardo DiCaprio at a red carpet event, the actor seemed strangely unfazed.

Seduik Also Tried To ‘Prank’ Gigi Hadid.

Not a red carpet, but still a pretty awkward interaction. Seduik came behind Gigi Hadid as she was leaving a show in Milan, picked her up, and got more than he bargained for when a (rightfully) furious Hadid fought him off.

Hailee Steinfeld’s Wardrobe Malfunction.

While Steinfeld absolutely stunned at the 2017 Oscars, her dress had a pretty big tear (look at the red circle in the image).

Stella McCartney Almost Ruined Rihanna’s Dress.

The designer’s heel nearly destroyed Rihanna’s whole look at the Met Gala. Luckily, everything turned out okay.

Selena Gomez’s Blue Hair At The Teen Vogue Young Hollywood Party.

To be fair, it was 2007, and Gomez was just a teenager at the time. But listening to her talk about her “edgy” blue hair is still pretty cringe.

Tiffany Haddish Was Not Wearing A Costume.

At an afterparty for the infamous 2022 Oscars, Haddish corrects Lauren Zima, who said the comedian had a “costume change.” It’s actually Dolce & Gabbana.

Issa Rae Is Asked What She’d Call Her Memoir.

Giuliana Rancic interviewed Issa Rae at the 2018 Golden Globes, asking what a potential memoir for the actress would be called. I guess she forgot that Rae already wrote one.

Sutton Stracke Goes Silent On The People’s Choice Red Carpet.

When asked if she want Lisa Rinna to return to Real Housewives of Beverly Hills , Sutton stayed absolutely silent.

Reece Witherspoon And Felicity Jones At The 2015 Oscars.

Pictures might be worth a thousand words, but this one of Jones and Witherspoon shaking wrists with an awkward staff member between them speaks a million.

Jessica Chastain And Oscar Isaac’s Weird Red Carpet Flirting.

While promoting Scenes From a Marriage , Isaac went ahead and kissed Chastain’s elbow… for some reason.

Debra Messing Drags E!… While Being Interviewed By E!.

Messing was pretty quick to point out to Giuliana Rancic that the male hosts on E! get paid a lot more than the female hosts.

Jennifer Lawrence Trips At The 2014 Oscars.

The actress is no stranger to awkward moments, and her tripping on the Oscars red carpet is just one of them.

It’s Not, In Fact, The First Time She’s Done It.

The year before, when going to accept her Best Actress win, Lawrence tripped on her way up to the stage.

Leslie Mann Copped A Feel On The Red Carpet.

While promoting the movie The Other Woman , Mann grabbed Cameron Diaz’s butt for some unknown reason.

Isaac Mizrahi Also Copped A Feel Once.

The interviewer decided live television was the place to grab one of Scarlett Johansson’s breasts in order to feel the padding on her dress.

Jennifer Lawrence Asks About Josh Hutcherson’s Rash.

The Hunger Games star asked about her costar’s rash while passing him by on the red carpet. Why? Why not?

Amy Schumer Talked About Her Tampon.

At the 2016 Emmy’s Schumer let everyone know that she had an OB tampon on. Not that anyone asked.

Scarlett Johansson Clapped Back At Ryan Seacrest.

The actress called Seacrest’s question about her shoes “ridiculous.” And to be fair, it really was.

Jim Carrey Mocks Icons At New York Fashion Week.

Also, according to Carrey , none of us exist. There’s some food for thought.

Jack Harlow Tells Emma Chamberlain He Loves Her.

Their entire exchange is pretty awkward, but after Harlow says, “love you, bye,” Chamberlain looks visibly confused.

Mayim Bialik Sets Her Education Record Straight.

The interviewers clearly didn’t know that the Big Bang Theory alum is actual a neuroscientist in real life.

Gary Bussey Interrupts Ryan Seacrest’s Interview.

When trying to interview Laura Linney and Jennifer Garner, Gary Bussey interrupts to talk to Seacrest. And then he kisses Garner on the neck…

This Eye-Catching Dress Worn By Sharon Stone In 1995.

Were silk bedsheets ever in style as something people wore? Probably not.

Lady Gaga’s Oscar Gloves.

The dress Gaga wore to the 2015 Oscars was stunning. The gloves, though, looked like the kind you’d use to wash dishes.

Chrissy Teigen At The AMAs.

The slits on Teigen’s dress might’ve been too high, and she definitely looked uncomfortable wearing it.

Scarlett Johansson’s 2015 Red Carpet Look.

The dress itself is mostly fine. But between the hair and necklace, it’s a fashion don’t.

That Same Event, John Travolta Tried To Kiss Johansson.

Poor Johansson just couldn’t catch a break that night. She looked more than a little uncomfortable when Travolta came by.

Machine Gun Kelly And Megan Fox Touching Tongues?

Back in 2021, Megan Fox and Machine Gun Kelly’s weird displays of affection were still pretty new. It’s still weird now, but a little less unexpected.

Kourtney Kardashian And Travis Barker Followed Suit.

In 2022, Kardashian and Barker had an equally uncomfortable PDA moment. When will celeb couples learn?

Jennifer Garner Trips At The 2013 Vanity Fair Oscar Party.

Celebrities are just like us, in that even they can’t walk in a long dress and heels that well.

Jason Derulo Falls At The MET Gala. Or… Does He?

Not only is that not a picture of Jason Derulo, it wasn’t even taken at the Gala .

When Nicki Minaj Shaded Miley Cyrus At The VMAs.

Again, not a red carpet moment. But Nicki’s “Miley what’s good?” is both iconic, and a little awkward.

Courtney Love Interrupts An Interview With Madonna.

Interrupting an interview is awkward enough, but doing so by throwing a makeup compact at Madonna? Just plain odd.

When Lil Nas X’s Outfit Didn’t Get The Reaction He Wanted.

“I’m not saying I’m hating on the fit but, let’s move on.” Probably not the best thing for an interviewer to tell a star, whether it’s the truth or not.

Jack Harlow Shooting His Shot With Saweetie.

We probably won’t know if it worked or not, but it sure was a little awkward to watch.

Macy Gray Let Everyone Know When Her New Album Was Out.

Of all the statements to make on a dress, this one is pretty inoffensive. But still weird.

Conor McGregor Tried To Fight Machine Gun Kelly.

Good thing there were plenty of bodyguards around to keep the fight from getting ugly.

Kanye West Drinking Hennessy On The Red Carpet.

Mere hours before he interrupted Taylor Swift at the 2009 VMAs, West was caught drinking right on the red carpet.

Elsa Hosk Stopped It All To Find A Lost Earring.

2019’s Venice Film Festival literally could not go on until Hosk found that earring.

Angelina Jolie, Billy Bob Thornton, And The Blood Vials.

Everyone thought it was strange how the then-couple would wear their blood around their necks. But according to Thornton, it wasn’t that weird.

Speaking to PEOPLE in 2018 , he stated that they just put a little bit of blood on the necklaces. “But by the time it came out in the press it sounded like we were wearing a bucket of blood around our necks.”

Kristen Stewart Takes Off Her Shoes.

Those high heels celebs wear definitely aren’t comfortable, and at the 2018 Cannes Festival, Stewart decided to take a stand against them.

This Dress That Jennifer Hudson Wore In 2007.

Between the dress and the weird little jacket, this outfit did nothing for Hudson.

Nicole Kidman’s 1997 Oscars Dress Had Joan Rivers Heckle Her.

Kidman completely ignored Rivers, who’d shouted, “Nicole! Come tell me why you wore such an ugly color! ”

Michael Cera Falling In Slow Motion.

While goofing around with Catalina Sandino Moreno, Cera fell. And then, just kept falling.

The Outfit Itself Was… Interesting, To Say The Least.

Their matching black outfits really didn’t do either of them any favors.

The Mess That Was ‘Don’t Worry Darling,’

Between rumored feuds between Florence Pugh and Olivia Wilde , not to mention “Spitgate” and a number of other strange controversies , there were plenty of awkward moments to be had.

Will Arnett Having To Explain That He Doesn’t Have A Wife.

A year after splitting with Amy Poehler, Arnett was asked how he got ready with his wife for the Emmy Awards ceremony, to which he responded, ” I don’t really have a significant other… She doesn’t exist .”

Rashida Jones Had To Clarify Her Skin Color.

Danielle Demski for TNT asked how Jones was able to look so tanned. Jones, the daughter of Quincy Jones and Peggy Lipton, responded with, ” I mean, you know, I’m ethnic .”

Melissa Joan Hart’s Not-So-Blended Makeup.

While attending a premier for Frozen , Hart’s makeup artist clearly didn’t blend properly.

Vara Farmiga’s 2010 Oscars Look.

The ruffles, which kind of resembled a fungal colony, were definitely one risk that didn’t pay off.

Hilary Swank In 2003.

On one hand, the color is nice. On the other hand, the dress looks a little… cheap.

Adam Levine Censoring Behati Prinsloo’s Nip Slip.

At least the awkward moment from 2015 prevented something that would’ve been even more awkward.

Katherine Keener’s Black Dress From 2006.

The top looks like a camisole, and the bottom looks like a ballgown. It just doesn’t make sense.

Juliette Lewis’s 1992 Hair.

Talk about an odd hairstyle choice to go with that outfit.

Gwyneth Paltrow’s Infamous 2002 Oscars Dress.

Paltrow may be an acting powerhouse, but this outfit is an absolute fail.

Jennifer Garner’s Icy Dress From 2003.

It looks like something Elsa would wear, minus the incredibly constricting chest area.

Kate Hudson’s Baffling Outfit From 2001.

The dress itself is quite nice, but gets ruined by that shoulder piece.

J-Lo And Luciana Perez Showed Up To The 2015 Oscars In The Same Dress.

The dress at least works for both of them. Still, that’s got to be awkward.

Gisele Bündchen’s 2005 Oscars Look.

Bündchen’s dress seemed pretty out of place for an Oscars red carpet. It looks more like something you’d wear on the beach.

Gwyneth Paltrow’s 1999 Oscars Dress.

Some argue that this is the most beautiful Oscar dress in existence. Cosmopolitan, on the other hand, thinks it’s pretty overrated .

Tim Robbins In 1995.

Robbins is dressed in a suit that kind of resembles outer space. A spacesuit, if you will.

Daryl Hannah In 1992.

It would have actually been a nice dress, if the skirt section looked less like it was just pinned on there.

Julia Roberts Really Wore This In 1990.

The more you look, the worse it gets. The dress is an odd color, has no shape, and has a weird thing going on with the bottom.

Lizzy Gardner’s Credit Card Dress From 1995.

The dress is so bad, it’s almost actually good. But not quite.

Jared Leto’s 2015 Ensemble.

He wouldn’t have looked so out of place if he were going to the prom. Or if it were the 1980s.

Jon Bon Jovi In Whatever This Is Circa 1991.

No suits should ever be made entirely out of velvet again.

Tyra Banks In 1996.

The dress is definitely a product of its time, but not in a bad way. The hair, on the other hand, is an absolute travesty.

Nicole Kidman’s 1996 Gown.

Is it a red carpet gown? Probably not. Is it a nightgown? Well it definitely looks like one.

Edy Williams In 1993.

Apart from being a very odd shade of pink, this dress feels like it could’ve done well in an ice dancing show.

Basically Anyone Wearing Sunglasses As A Fashion Statement.

Are they supposed to elevate the look, or make them look more causal? Because either way, they just don’t work.

Whoopi Goldberg’s 2014 Oscar Layers.

The button down shirt under that dress? Not as good as Goldberg probably thought it’d be.

That Time Angelina Jolie Kissed Her Brother.

Jolie attended the 2000 Oscars with her brother, and won for her role in Girl, Interrupted . Years later, she addressed the infamous kiss, though:

“First, we’re the best of friends”, she said to PEOPLE . “And it wasn’t some odd open-mouthed kiss. It was disappointing that something so beautiful and pure could be turned into a circus.”

Sally Kirkland Over The Years.

It’s definitely safe to say that the actress is known for her… interesting red carpet looks.

Anne Hathaway In 2013.

The dress’s color isn’t very flattering against Hathaway’s skin. But the glaring nipple outlines are, well, glaring.

Mariah Carey’s 2010 Oscar Dress.

There’s something pretty off about this dress. And not because it’s asymmetrical. Well, not completely because of that.

Juliette Binoche Vs Heidi Klum.

The dresses came from different decades, are made from different materials, and still both have those odd collar things. And neither of them work.

Celine Dion Tried Something In 1999.

The hat, the sunglasses, the fact that the blazer is on backwards. Nothing makes sense.

Geena Davis In 1992.

It’s an attempt at a moulin rouge kind of outfit. The keyword here is “attempt,” though.

Heidi Klum’s 2009 Dress.

Something about the cut and material just don’t work. It definitely doesn’t feel like a red carpet outfit.