Everyone who has ever had a smartphone has taken an embarrassing selfie. It’s the way of the 21st century. Now if everyone would just be themselves, there wouldn’t be any embarrassing selfies. Because we all know embarrassment comes from not being yourself or from being judged by someone who refuses to let anyone know who they really are. But since neither of these things will ever happen, we’ll just have to live with the fact that embarrassing selfies are a huge thing. This problem even affects the richest and most famous of us all. In fact, it seems like they tend to have even more embarrassing selfies than the rest of us.
Anyway, even celebrities take the worst selfies, which is okay. But what is not okay is putting them online for the world to see. Want to show that you’re just a normal person with flaws? That’s great! Otherwise, just keep your selfies to yourself. They don’t make you look good, and it often looks like you’re trying too hard. When we follow our favorite celeb on social media, we become confronted with their most weird, embarrassing, and downright disturbing selfies every day. At least there’s one good thing about all these awful selfies. They make us never want to take another picture of yourself again, even a good one. I don’t know about you, but after looking at these 15 celebrity selfies, I am done with selfies for good.
15 Amanda Bynes
To be fair, Amanda Bynes doesn’t have all those awful stories of being the worst costar in history. She just got really messed up on drugs and alcohol, and we can't hate her for having personal problems. However, this really is her worst picture ever. Even the photos of her in court are more flattering. What was going through her head that would make her think that posting these online would have positive results at all?
Well, in 2017, she finally admitted that she had a problem and looked for help. She’s now back in the running for having a normal celeb life. She said she got so bad that they put her in the psychiatric ward, which was a big turning point for her. After several DUIs and hit-and-runs, she had enough. But this was after dozens of selfies like this that tainted her rep and turned us off selfies for life. If Amanda didn’t know what she was doing, how can we be sure that we do?
14 Kim Kardashian
The most iconic sunburn selfie of all time: Kim Kardashian’s summer of 2009 burn. This just gives us another reason to stop wearing those huge glasses that men hate on women. Kim K proved this when she fell asleep while on vacation in Mexico. She fell asleep sunbathing with those giant Prada glasses lying on her face. When she woke up, she highly regretted it, as she now had the reddest raw skin, which was peeling to no end. What would you do if this happened to you? Take a selfie and post it online? That’s what she did.
Thankfully, her makeup artist did an amazing job covering it up so she could appear on CW the following day, but the memory will haunt her – and us – forever. She spoke out about it as it happened: “My whole body is burned but my face looks the worst because of the glasses. I will never wear sunglasses when sunbathing again!” We hold her to that. She said, “Everyone here is making fun of me! Look at Reggie's teammate and friend Bobby starting with the jokes.” Why would someone post a photo of themselves looking like this? It is painful to even look at her.
The whole au naturel hair thing (except on your head) got really popular in 2014, and of course Madonna was a shoo-in for the whole stand women were taking. She was one of the first to make it okay, and today, one in four women refuse to shave their underarms. That’s a lot! But back in 2014, the trend hadn’t picked up quite yet so Madonna was ridiculed for it.
She posted a photo on Instagram with the caption, “"Long hair... Don't Care!!!!!! #artforfreedom #rebelheart #revolutionoflove,” and boy, did people flip out. Even though today Miley Cyrus, Julia Roberts, Kristen Stewart, Mayim Bialik, Demi Moore, Cameron Diaz, and more have admitted to not shaving, Madonna got the bad rep for it. She’s the one who got embarrassed, but then again, her hairy photo was one of the most tasteless of them all. Proving you don’t shave is one thing for a cause, but flaunting it is another.
12 Jessica Simpson
There was genuine confusion here when many first saw this. I legit thought that Jessica Simpson was drunk and wearing a layer of phyllo dough on her face. It took me a while to realize it was one of her “beauty secrets,” which is a face mask. In 2010, she spent over $300 for a special face mask and tweeted a picture with the caption, “Thanks La Mer for the upper and lower zone radiant mask.”
Sales of the mask skyrocketed and $80 versions were back on the market. If she weren’t such a beautiful celebrity, she would have been made fun of. We need you to know that just because Jessica did it, it doesn’t mean your tweet would get thousands of retweets. So don’t do it, and phyllo dough will not give you Jessica Simpson’s skin, and neither with that $350 treatment. It’s going to take a lot more than that.
11 Chrissy Teigen
If there’s one celebrity who is not afraid of embarrassing herself, it’s Chrissy Teigen. As a model and John Legend’s wife, her word is the gospel and no one questions the crazy things she does. But why in the world would she make such an ugly face and post it online? Well, because BuzzFeed was challenging women to make the ugliest face that they could and show it to them. Turns out, Chrissy was up to the challenge and did just that. She wanted to win bragging rights for the “grand prize.”
Since we all know how beautiful she is, this did little to her reputation, but it did let us see her in a light that many never wished to see. It did let us know that, nope, she is not just a pretty face. She’s something else… something else entirely. We’re not sure what yet, but it’s something only Chrissy can be.
10 Cara Delevingne
Cara Delevingne doesn’t care what anyone thinks. She’s a gorgeous model who could really not care less what you say about her selfie. She’s posted a lot of them. Some with a contorted tongue. Some with a donut or burger stuffed in her face, and some that we don’t really know what’s going on in. But as far as strange and embarrassing goes, we say this one is the winner.
Let’s start by saying that it’s not mud on her face. Her Instagram caption says it all: “I can't believe a bird actually shat on my head! Meeehhhh!! Well at least it's good luck.” Indeed it is good luck. This was in 2013 when Cara had just over one million followers on Instagram. Today, she has 40 million followers. That’s quite the jump! I doubt it had much to do with that bird poo and more to do with that pretty face it got on, however.
9 Iggy Azalea
Who is this beaut, you might ask? It’s your very own Iggy Azalea. Why does her face look like a jigsaw puzzle? That’s not as simple. She’s known for sharing cute and sexy selfies of herself on Instagram. But this one was labeled a “weirdo” selfie in no time. She labeled herself when she captioned the photo, “Just being a little weirdo getting laser beams shot into my head and stuff.”
Exactly what kind of procedure she was getting, I don’t know, but sharing the photo was a little disturbing. She looks like a cyborg. A pretty cyborg that might save the world… or destroy it. Who knows these days! Maybe Iggy is a cyborg bent on taking over the world with her music and strange selfies. This could be her getting her human makeup done…We’re onto you, Iggy… and your friend Nicki, too. We know the truth! It’s all coming together.
8 Lindsay Lohan
Do we ever know why Lindsay Lohan does what she does? How did she turn into the promising redheaded teen who rivaled anyone in beauty to the dried-out blonde who looks like she’s on every drug in existence? We don’t know. She’s cleaned herself up more times than we can count, but she always goes back. If you look at this one you’ll see that she doesn’t look too rough, but with an alcohol addiction present, looks can lie.
She was likely drunk when she let this photo out to the public. Although it’s not her worst by a longshot, it really showed the worst part of her at the time when she hadn’t gone too far yet. She had kept her clean image but threw it out the window with pictures like these. No wonder so many actors hate working with her. Have you heard the stories that costars have told? Not pretty.
7 Ricky Gervais
Ricky Gervais is quite the character. Like Chrissy, he’s not afraid to show the world whatever they want to see. Some call it a cover-up of his true self, and others say he couldn’t be more himself! Only he knows the truth. The point is, this photo is so outrageous that we’re embarrassed for him. Why is he in a bathtub? What happened to his teeth? And why in the world is he making that pose?
Of course, it’s all explained in his caption for the image, which he posted on Twitter. Fans of his couldn’t get enough and so he did a whole photoshoot (more on that soon). He really is his own species. One that I wouldn’t mess with because no one wants to face a crazy comedian in a bathtub whose only goal is to do something that no one has done before.
6 Miley Cyrus
Miley Cyrus has had the worst luck with headlines. She’s been on the news for all of the wrong reasons. We can’t say that it’s not her fault with selfies like these. Seriously? Who in the world posts a photo of themselves on the toilet? Not very many people. Who posts a photo of themselves on the toilet with severed fingers on their jacket? Maybe a couple. Now who posts a photo of themselves on a toilet with severed fingers on their jacket and a piece of corn in their hand? The one and only Miley Cyrus!
Eating while on the toilet is absolutely disgusting, but that’s your business. However, taking a photo of it (and posting it on Instagram), makes it everyone’s business, so we can judge. And the judge says… ew! Miley has done a lot of awful things in her career but I think this one tops them all.
5 John Mayer
Now do you think that John Mayer purposely led us to believe that this photo is natural? Because we all know photo filters when we see it. We all use them often, actually, and it gives men an excuse to get smooth skin without wearing makeup. But this is too much. They look like Ken dolls without separated teeth and plastic cheeks.
I hope that this photo of John and his friend from College Humor is a joke, because we all know that as handsome as they are, their skin is not that smooth. No one’s is. But to post such a fake looking photo without a word is just asking for thousands of comments calling you out. Sorry, John Mayer, but you’ll never live this one down. No one holds it against the College Humor guy, though. It’s either because he’s not famous enough or it wasn’t “his” photo.
4 Katie Price
Katie Price is a television personality, businesswoman, model, author, singer, and designer. Not gonna lie, she’s never been anything but beautiful, but this photo is one shocker. Her intense eyes could seriously kill someone, but that hair proves that she doesn’t wake up looking like a model. For a celeb who usually looks perfect and who isn’t afraid to bare it all, well, you can see how this one might embarrass her. I’m not sure whether I am embarrassed for her or just jealous.
I mean she does look amazing, but she’s also a mess. Some may say she doesn’t look sober. I have no idea why she’d let it hit Twitter when there’s so many more photos of her in bed that look way better than this one. This may be posed but it wasn’t prepared for, that’s easy to see.
3 Ricky Gervais And Conan O'Brien
This time, Ricky brought Conan O’Brien into this. Now they’re both in the bathtub and things are about to get personal. While the other photo was posted earlier this year, this one was posted in 2013. Makes me wonder if this was all the same shoot or if he really likes bathtub selfies. It’s an odd interest, but whatever floats your boat, I guess. The only thing stranger and more disturbing than a bathtub selfie, though, is one with two people rather than one – two comedians, at that. I know, comedians in the buff are more disturbing that anyone else, but since they want to make you laugh, that means they will go to greater lengths to entertain you, even at your own expense.
If you think the picture is intense, then you should hear Conan tell the story behind the picture. Now that will knock your socks off.
2 Madonna Part 2
While the hairy pits had a point, I really don’t see the point in this photo of Madonna drinking. A photo of a celebrity drinking is old news, but one of a celebrity drinking that they took themselves is pretty new. You don’t usually want to associate yourself with the party lifestyle unless you look in control and super fine. Madonna looks like she’s near the end of her life, though, and her eyes are so intense in the worst way: red, tired, and not ready to drive home. I hope she had a designated driver because she wasn’t all there for this picture. At least she can live it down since she had an excuse for what she did. Others are not so lucky.
1 Miley Cyrus Part 2
Again, Miley? Again? How many times are you going to post photos of yourself on the toilet? This one isn’t as bad as the last one, at least. I really hope that Miley is past the stage of posting icky photos of herself. She’s so pretty and has the potential to have such class. However, she ruins it by wearing the worst outfits and posing on the toilet with the worst bright lipstick she could find. I feel sorry for her. I mean, who in their right mind would actually take a photo of themselves on the toilet… with toilet paper in their hand?
There’s one good thing to say about this. She can’t really get any worse. Unless, of course, you add corn to the mix. That’s just not right. Miley has, and forever will, win the messed-up celebrity selfie games. Props to her! I know she would be proud of the title that she was so deserving of.
Leave A Comment
Looking for an AD FREE EXPERIENCE on TheRichest?Get Your Free Access Now!