embarrassing celebrity photos, gifs, and videos

We all have those moments we don’t want to ever think about again. If you’re a regular person, the worst thing that could happen is that your friends capture it with a photo or a video. You, most likely, won’t become a viral sensation.

However, if you’re famous, you will find yourself competing for the most embarrassing celebrity photo. Or worse, a video.

We don’t want to be malicious, but some meme-worthy moments belong in a hall of fame. From having one too many or being part of an “artistic” photoshoot to accidental peeing and showing your privates, here are the best of the worst: embarrassing celebrity photos we all need to see. Just for a chuckle, not much more.

Hottest celebrities at their worst

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

Imagine being followed wherever you go. The downside of being famous is that you never know when a curious fan or paparazzi might show up.

That’s, however, a small price to pay for many. From being worshiped to getting Gucci dresses and Hermes bags to having your sports teams, and jets it’s pretty easy to see what makes fame so appealing…

Needless to say, one accidental photo which happens to be both embarrassing and funny won’t make a vast difference.

Yet, some of the best photos come from celebrities themselves. To make the world a better place, they often overdo it and confuse reality with filters or questionable selfies.

Let’s check out various celebrity fails to pick the most embarrassing celebrity photo or moment. Perhaps a blast from the past?

#1. Leo’s gone bananas

embarrassing celebrity photos
embarrassing celebrity photos

Leonardo DiCaprio seems to have a side we know nothing about. It involves an extraordinary pair of jeans, bananas, and one heck of a weird haircut.

We understand that this is young Leo rising to fame, but it’s quite bizarre. Who knew that a photoshoot from 1995 would become a symbol of all embarrassing celebrity photos?

#2. Harry Styles and the shoe

embarrassing celebrity photos
embarrassing celebrity photos

Harry Styles is one of the least problematic celebrities in the world.

Yet, the artist had to take one for the team. In 2015, a fan of One Direction was so excited that she decided to take off one shoe and punch poor Harry in his private place.

It wasn’t Harry’s fault, but still… We are sure he wishes cell phones didn’t have cameras. At least this one time.

#3. J-Law at the Oscars

embarrassing celebrity photos
embarrassing celebrity photos

We don’t want to give any awards to Jennifer Lawrence ever. It’s clear why: she always does something silly and ends up hurting herself and her Dior outfits.

But, Lawrence isn’t alone. Many celebrities felt her pain, but one managed to go a step further.

#4. Justin Bieber getting to the stage

We saw Justin Bieber fall from grace, and from the stage. Well, in case you forgot, here’s a reminder:

embarrassing celebrity photos
embarrassing celebrity photos

#5. Bieber on stage

It’s like Justin Bieber’s worst enemy is gravity!

embarrassing celebrity photos
embarrassing celebrity photos

#6. Justin Bieber again

Well, that’s okay; every star fell off the stage at some point. But what happened here? Freshly waxed floor?

embarrassing celebrity photos
embarrassing celebrity photos

#7. And again

Just when we thought we’d seen it all, young Justin finds the doors. It’s gotta be tricky being super famous and having so many issues with such simple things, like the doors.

embarrassing celebrity photos
embarrassing celebrity photos

#8. Bieber vomiting

embarrassing celebrity photos
embarrassing celebrity photos

Justin Bieber doesn’t just win the most embarrassing celebrity fails. He also threw up on stage, not once, but twice in one evening.

He blamed too much milk, but we have to point out that there’s a pattern here. Bieber never does anything once.

#9. Fergie’s pants

embarrassing celebrity photos
embarrassing celebrity photos

It was 2005, and Fergie was the bad girl every teenager wanted to be. During a performance, she clearly had to go, so she did.

Hey, it’s no big deal. Toddlers do it all the time. Perhaps it happened to you during a college party when you had one too many.

We’re not certain whether this was heroic or just plain celebrity fail. Even performers deserve a pee break, and we have to admire Fergie’s dedication to her craft.

#10. Taylor Swift’s MM moment

embarrassing celebrity photos
embarrassing celebrity photos

If it can happen to Kate Middleton, the real life Duchess, it can happen to anyone.

Taylor Swift is known for her well-crafted public image. She’s never too sexy or provocative. Yet, during a performance many moons ago, she showed a bit more than we paid for.

It’s one of those embarrassing moments she certainly wants to forget, but the Internet is forever.

#11.Taylor Swift’s Bieber moment

embarrassing celebrity photos
embarrassing celebrity photos

To be fair, this happened to many performers. Usually, it’s because of high heels and the nerves, perhaps one too many or something similar.

Lady Gaga, Madonna, Katy Perry, they all did it, but when Taylor does it, it’s a reminder that no one’s safe.

#12. Hailey Baldwin preaching

While we’re all for posting more realistic images, it’s not glow up if your face looks completely different.

There’s nothing wrong with enchantments, but being a hypocrite is a major turn-off. Also, Hailey’s a model, so telling others less genetically (or surgically) blessed what to do is Jaden Smith’s level of preaching.

#13. The most cringy celebrity interview ever

It’s not a photo, and it’s not a gif. Rather, it’s a whole freaking show.

Tom Cruise jumping on Oprah’s sofa because he was so in love with Katie Holmes was epic. As in epic fail.

The whole interview is weird, and we applaud Oprah for keeping things under control, at least partially.

#14. SJP doing something

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

Before she was Carrie Bradshaw, Sarah Jessica Parker was challenging her inner Flashdance.

From fashion and sweat stains to the actual pose, everything about this photo is just wrong.

#15. Ryan Gosling camouflage

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

We really want to know what the heck was Ryan Gosling thinking when he was posing for this photo.

The whole concept makes zero sense, but maybe it’s too artistic, and we just don’t get it. There’s no other explanation, except the most embarrassing celebrity photo ever!

#16 Zac Efron Dropping A Condom

It’s always good to remind people to have safe sex. But if you’re going on a premiere of a kids’ movie Dr. Seuss, perhaps you should be a bit more careful.

Zac Efron, lover of skateboarding groceries and dropping condoms on the red carpet. Oh, well… It’s not like when Cara Delevingne dropped a bag of baking soda or something that looks like it….

#17. Tom Hanks does a selfie

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

Hanks delivered many great roles, but taking a selfie seems to take away his acting skills.

To make matters worse, he actually thought it was a good idea to share his photo with the world. Hanks looks creepy, so it’s not relatable, not funny, but it is one of the worst selfies among celebrities.

#18. Robin Thicke’s touch

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

This is Thicke in 2013, after that super awkward performance with Miley Cyrus. But, hey, that was all for a good show. This, however, is a whole different kind of embarrassing, and it involved a married man squeezing a woman’s butt.

If this were his wife, it would’ve been cute. But it’s not, so it just looks dirty.

#19. Patricia Arquette running errands

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

An Oscar winning actress was spotted doing her thing around Los Angeles. Sounds normal and innocent enough.

But, why in the world did she forget to put on her pants? If you have the time to put a sweater around your waist, you had to have the time to pull on your pants, right?

#20. Bella Hadid is so over camel toes

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

The Cannes film festival always brings great movies from all around the globe, and for whatever reason, the most talked-about supermodels.

Bella Hadid showed us her underwear not once, but several times during her presence at this festival over the years.

At least she wore panties, unlike many other celebrities. And you thought camel toes were a big deal..

#21. Jennifer Aniston before fame

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

If you want to see what Jen Aniston would look like if she never found fame, look no further! It’s not that she looks bad, but that hair and that knit vest are too much, even for the early 90s.

#22. Tara Reid’s boob

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

What a day not to wear a bra…

As Tara Reid was posing before P. Diddy’s big party, her boob decided it’s time to go home. The actress later had to defend the fact that she was flashing the photographers:

“People act like it was the worst crime in the world. It was a mistake, you know!”

“But you would think my boob had popped out and shot Gandhi! My hooters are under control. I’m taped up now, totally. I’m using double tape. Double double tape. My boobs are going nowhere again.”

#23. Hilary Duff got engaged

A few years ago, former Disney star, Hilary Duff, got engaged to Mike Comrie, and they celebrated privately.

The paparazzi photos were over the top, but since we’re all adults, we’re allowed to laugh. So, here is Hilary showing how to have a happy ending.

This isn’t some slut-shaming. There’s no “but”; the two were on the balcony, and it’s not like the paparazzi lens went into their bedroom… It had to be said!

#24. David Duchovny’s truth

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

We have no idea why someone would invent a giant yoga ball or what’s with those silver leggings. Clearly, this was way back when Duchovny’s X-Files career didn’t quite kick-off.

We can’t say anything but what was he thinking?

#25 Justin Timberlake and Janet Jackson in the Nipplegate

During the 2004 Super Bowl halftime show, Justin Timberlake ripped off a piece of Janet Jackson’s outfit. It wasn’t supposed to reveal the boob, rather tickle our imagination.

Sadly, it turned into a witch hunt, and no one dared to say a thing about Timberlake. He apologized, as he should have the moment it happened.

It’s kind of embarrassing that we need to address that Janet did nothing wrong. Yet, the Nipplegate is one of the biggest celebrity scandals of the 2000s.

Celebrity moments we should be ashamed of

Nipples and old photoshoots should be laughable. But, Janet Jackson was abused by the media because of a wardrobe malfunction. Bizzare.

Even worse, everyone was laughing out loud when Britney Spears shaved her head. Or when Amanda Bynes had a breakdown.

No, we will not post photos because laughing at someone for having mental health issues is not helpful. That was on all of us, and in case you were too young to remember, consider yourself lucky.

These pictures prove that we all make mistakes and we aren’t doomed to repeat them unless we’re Justin Bieber. Since we are not going to open the Pandora’s box today, let’s finish it with a classic: Wham! and the 80s fashion!

embarrassing celebrity photos, gifs, and videos
embarrassing celebrity photos, gifs, and videos

And yes, George was very much embarrassed by this particular moment.