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“Unveiling the Cringe: The Most Outrageous Celebrity Photoshoots That Left Us Speechless!”

Added on October 23, 2024 inFree Facts and Fun

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Ah, the glamorous life of a celebrity! You’d think it’s all red carpets and Hollywood glitz, right? Well, not quite. Picture this: a star strolls into a photoshoot with an artistic director and a stylist at the ready, all set to capture that perfect shot. But what happens when it all goes wrong? Like, “Did I really just pose like that?” wrong. We’ve all had our share of awkward school pictures—hello, braces and bad hair days—but when stars like Mark Wahlberg flashback to their cringe-worthy moments, it hits hard. So grab a snack, settle in, and get ready to revisit some of the most hilariously unfortunate celebrity photoshoots that will make you feel better about your own photo fails. Want to explore more jaw-dropping mishaps? LEARN MORE.

Doing photoshoots for magazines, television, and promotions are just a part of the job description for a celebrity. Usually, they just show up and have an artistic director, stylist, and photographer spend hours making them look amazing.

But every once in a while something goes horribly wrong. It’s not the celeb’s fault. They’re just following instructions. But following the director’s orders can mean living the rest of your life with a cringe-worthy photo. If you thought your school picture from grade seven when you had braces was bad, wait until you see Mark Wahlberg’s photo from the Marky Mark days.

Oh No Keanu, What Is You Doing?

I want to defend Keanu because this photo was from before The Matrix, but he was still a well-known celebrity thanks to Bill And Ted’s Excellent Adventure. He’s looking off into the distance with regret because he knows this cross-legged pose is a bad idea.

The marble background, on the marble pedestal, with no shoes. It’s like an ’80s lounge bar meets grade school pictures.

This Photoshoot Was Miley Cyrus’ First Taste Of Controversy

Can we all just take a moment to reflect on the time where this was the most controversial thing Miley Cyrus did? The “racy” photoshoot was shot by Annie Leibovitz for Vanity Fair when Cyrus was just 15 years old.

Outraged parents called the photo “pornographic” and forced Cyrus to apologize. Fast-forward ten years later, and Cyrus recently reposted the photo saying she regretted ever apologizing.

Who Decided Covering Ryan Gosling In Wallpaper Was A Good Idea?

I always thought Ryan Gosling was so good looking that he could be covered in dog poo and still look sexy. Well, I was wrong. All it took was covering Gosling in wallpaper. Yes, this is the best looking floating head I’ve ever seen, but they didn’t have to do him like that.

Keep reading to see how the king of controversy put out a magazine cover that made the religious community outrageous.

People Think That Vogue Made Lebron James Look Gorilla-Like

When Vogue announced that LeBron James would be the first black man to grace their cover, fans were rightfully excited. But then they released the cover, and many were quick to point out that they had LeBron posing in a very ape-like way, aggressively bearing his teeth.

People couldn’t help but compare the cover to racist depictions of the black community as primal animals.

Silver Leggings Is Never A Good Idea

I want to have a nice long chat with whatever stylist managed to convince David Duchovny to put on silver leggings and pose on a ball. Did he know the artistic vision before he agreed to the shoot? Or did they just throw him on set with no warning?

In true X-Files fashion, “I want to believe” that Duchovny wasn’t a part of this.

Should Anyone Be Surprised That Kanye Went For The Jesus Look?

Kanye West has made a career out of pushing boundaries and igniting controversy, so was anyone actually surprised when Rolling Stone released a cover with a Jesus Kanye? Plus, Kanye has spent large chunks of his albums referencing Jesus and religion. This cover was controversial, but he’s done crazier stuff.

Continue on and ask yourself: what is the worst possible pose Sarah Jessica Parker could ever do?

Marky Mark Is All Sorts Of Funky

Look. The early 1990s was a totally different time. Everyone collected Beanie Babies, The Macarena was a #1 hit, and Mark Wahlberg was living in an alternate universe as Marky Mark and the Funky Bunch.

This photo of him is as Marky Mark as it gets. I’m sorry, but no amount of abs can make of up that wild upper lip.

It Wouldn’t Be Controversial If A Kardashian Isn’t Involved

Ah, Kylie Jenner, the first of the Kardashian clan to grace this list. When Jenner came out with this wheelchair-BDSM inspired photoshoot for Interview Magazine, the disabled community was rightfully upset.

They have been marginalized from society for years, but Kylie’s attempt to capitalize on that fell flat. Sorry, Kylie, but this photoshoot will haunt you forever.

No One Wanted To See This Spread Eagle

This is one of the photos that you look at and immediately know is wrong, but you can’t stop staring. Maybe it’s Sarah Jessica Parker’s stone cold expression, or maybe it’s the awkward water bottle placement right between her spread legs. Either way, it’s one of those photos we’d be happy if we never saw again.

The next few photos celebrate the cringiest boy band photoshoots from an unforgettable era.

The Coolest NSYNC Has Ever Been

I understand that frosted tips were a trend in the late ’90s, but this is taking it a step too far. Not sure which one is better: Lance Bass’ one frosted eyebrow or Joey Fatone’s fully frosted beard.

There’s a 110% chance that this photo was taken for a teen magazine and this photo hung on the walls of thousands of teen girls bedrooms. But just because it was popular, doesn’t mean it’s right.

Praying For The Comeback Tour To Actually Work

Stay with me, because there’s a lot to unpack with this Backstreet Boys photo. A.J. looks like he’s a mob boss, but Brian is right beside him striking a pose that would be much more appropriate crouched down beside his 1983 used Chevy Impala.

Then we have Kevin in the middle in a dress vest even though everyone else is in bowling shirts. But nothing can top Nick’s alter boy persona. Oh ya, and Howie is there.

JT Looks Like He’s Crying On The Inside

Of course, Justin Timberlake gets his own shoutout for bad photoshoots. This Christmas themed shoot is as tacky as it gets. For some reason, JT looks like he drank a few too many rum and eggnogs and drunkenly wrapped that tinsel around his neck himself.

The celebrity coming up dressed in redface for a magazine cover, and yes, it’s as bad as you think.

Why Is Madonna Eating A Goldfish

The only good thing about this photo is that you’d have no idea this was Madonna unless we told you. Maybe that’s why she’s eating a goldfish. She’s just trying to find a good pose that hides her face from the camera.

There’s really no other reasonable explanation why Madonna would do this, so we’re sticking with it.

Back When Sexy Photoshoots Were A Necessity In Hollywood

Are you able to figure out which actress this even is? Believe it or not, it’s Jennifer Garner. In her defense, every aspiring actor and actress had a “sexy” photo in their portfolio in the ’90s and ’00s, but they’re usually not this bad.

That middle shirt button is hanging on for dear life.

Tip: If They Dress You In Redface, Walk Off The Set

This is one of those moments where you have to wonder how much say the celebrity has in their photoshoots. I’d like to believe that Michelle Williams would have said something about this. Especially while she’s watching herself get hair and makeup done in a way that’s blatantly appropriating Native American culture.

Keep reading to see which Friends star looks just as confused with their photoshoot as we are.

Whatcha Doing With Those Bananas, Leo?

It doesn’t matter how much of a dreamboat you are when your arm is stuck in an unknown fruit and you’re casually holding up three bananas.

The icing on this cake is that he looks like he’s watching paint dry. We’re not very excited about this photoshoot either, but you could try and fake it a bit, Leo.

Even Jennifer Aniston Doesn’t Know Why She Did This Photoshoot

This must have been before Jennifer Aniston’s Friends days because she does not look like the sexy, confident, Rachel Green that we all know and love. The baggy jeans, awkward crochet vest, and button up shirt make her look frumpy.

She knows it too. Aniston is throwing up her hands saying, “I have no idea why I let them convince me that this looks good.”

Why Does Eric Bana Look Like He’s Actually Enjoying This Photoshoot?

Okay, Eric Bana literally played the mighty Greek hero Hector in Troy, so I don’t understand why he has done this to himself.

This photo honestly looks like Bana was supposed to be doing headshots then someone saw a fake flower and gave it to him as a “fun prop.”

Sandra Bullock Has That Look In Her Eye

If we put aside the fact that Sandra Bullock is casually flashing an empty parking lot, there are still a lot of unanswered questions. Why does her jacket look like Mylar rescue blanket? Why does she have a set of boxing gloves hanging off her arm?

And why does she have that incredibly intimidating look in her eye? Help.