Photoshoots These 15 A-Listers Regret

We have to admit that this article was totally inspired by Nicki Minaj and her latest break-the-internet endeavor. If you haven’t seen the latest cover of Paper magazine, then you have to check it out. The flamboyant rapper, who has pushed the limit for years, is featured in triplicate. Nicki Number One sits in the center, wearing only pasties and booty shorts. Nicki Number Two stands and reaches down towards Nicki One’s bare "girls". And Nicki Number Three kneels between Nicki One’s legs, with her tongue out all the way. The cover is entitled Minaj-A-Trois, the most glaringly obvious pun ever.

Nicki is surely proud of her photoshoot right now, but it got us wondering, what will she think of it ten years from now? She might be a little shocked at herself, and at least a little embarrassed. And Nicki Minaj is not alone. Dozens of celebrities, from Miley Cyrus to Emma Stone, have posed for some very weird pictures.

Some of these photos could have been hot, but then they got weird. They could have been an artistic statement, but then they got cheesy. Either way, these celebs must look back and say, ”What was I thinking?”


15 Emma Stone

via Poringa!

Emma Stone is one of those Indie-type actresses who always wants to push the limit with the photoshoots. In doing our extensive research, we’ve discovered quite a few shots of Em that were highly awkward. In this pic, she has one of the most clueless expressions on her face. We are not sure how this photo is supposed to make us feel. Is she supposed to be hot? Is this supposed to be funny? She took this pic in GQ, and there’s another pic at this shoot, with Em wearing a black one-piece swimming suit and an afro wig, that’s like three feet high. We’re not sure what that is supposed to mean either. Sometimes, these photographers just get a crazy idea, and the celeb is just too distracted to say no. The weird photos haven’t affected Emma’s career, though, which couldn’t be any hotter.

14 Jennifer Aniston

via Pinterest

Here is a terrible idea. Let’s take one of the hottest Hollywood actresses of a generation and put her in the frumpiest outfits we can possibly find. Let’s just head on down to the Salvation Army and pick up an outfit that doesn’t fit nor match, then we’ll just have her stand there and smile. This is one of the strangest shots that we uncovered in our research just because it is the opposite of provocative in every way. Aniston is no stranger to weird shots either. She did a photoshoot for Allure magazine that was very odd. Her skin was really shiny, and her eyes were glossed over. I think she was supposed to look like a doll, but she ended up looking more like a corpse. Very cringy. She was in another shot, during the peak of Friends, where she sat on an oddly-shaped couch/ottoman thing.

13 Angelina Jolie

via Daily Sun

Here is an A-list actress who has had so many identities throughout the years. From her early modelling days, to her young Oscar win, and then the goth, the lesbian, the homewrecker, the mother, and the philanthropist. We’ve tried to keep up the best we can. Photoshoots are a great record of all the stages and children that Angie has adopted. She started out her relationship with Brad Pitt via a controversial photoshoot. Remember that one? She and Brad, who was married at the time, were featured in several shots playing house. She was the mom, he was the dad, and then there were various models and settings, which made them appear to be the oligarchs of a perfect family. Future ex-wife Jen Aniston must have seen those pics and has was like, “Uh, dude, wtf?” Divorce followed soon after, and now Brad and Angie even split. You gotta join #TeamBrad after seeing Angie’s odd photo history. What on earth is she doing in this one?

12 Jennifer Love Hewitt

via Pinterest

Now, this isn’t the official final product photo, but it does show a professional photoshoot with the not-quite-on-the-A-List-anymore star, Jennifer Love Hewitt. This photo doesn’t look very awkward, but it makes you feel awkward for the poor girl. She’s obviously trying to do one of those smoldering hot seashore shots, with the lust in her eyes and the wind in her hair. Too bad the wind is also filling up her skirt. The star is having a hard time stopping the wind from lifting the fabric. It’s so bad that Love is actually pushing the skirt down with one arm, while she’s laughing about it. We’re not sure what came out of this official shoot. Maybe they got a good shot of her genuine smile as she fought the breeze on this beach. We’re just hoping, for her sake, that they cropped out the wind-swept skirt. We also hope that she lands an awesome job again soon. Been too long for Love.

11 Julia Roberts

via Pinterest

This photo looks like, what, early 1990’s, right? Isn’t that about the same time that Disney did the Aladdin movie? We’re wondering if Julia thought she could maybe get the genie part, before Robin Williams swept in and nabbed it. We’re thinking, maybe Julia, who was obviously not right for the role, knew that she had to try hard to convince the casting directors to hire her. So she walked into the Disney studio, dressed as a full-on genie. She might have even auditioned for Aladdin too, because their wardrobe is pretty similar. Actually, this theory is bunk, and Julia just picked out a crazy vest for picture day. This looks like a younger Julia, so she wasn’t quite as fashion-savvy as the Julia of today. Lately, Julia has been busy promoting Wonder, her latest feel-good film, which has gotten some pretty favorable reviews, if you like sappy mush.

10 David Duchovny

via Pinterest

So, now we know where Miley Cyrus got her idea for the “Wrecking Ball” video. Seriously, doesn’t this shot look eerily similar? The lighting and colors all seem to match up. Even David Duchovny’s outfit looks similar. Miley has told James Corden that she was higher than a kite for the shooting of that video and that she is usually high for everything except for hosting award shows. Okay, so Miley has two good excuses for the Wrecking Ball video. One, she was higher than Cheech and Chong, and two, the song was called wrecking ball, so it was an obvious move. What’s David’s excuse?! Um…hard to answer that one. Was he trying to look attractive? Was he dying for an excuse to wear his favorite silver leggings? Who knows? But looking back, he must be embarrassed by this one.

9 Jessica Simpson

via Pinterest

Not sure how to caption this shot. The first thing that comes to mind is an insane asylum. Like, Jessica Simpson was going nuts, and this was the only safe place society could contain her. Things have come a long way since then, but when I was growing up, they had rooms like this in my middle school. If some kid was throwing a fit, they’d just put him in a room, which was wall-to-wall with padded carpeting. That is no lie. And this was in the American Midwest in the 1990’s. What did they do to ornery kids back in the 1950’s? Probably locked them in the Fit Room for a month. Who knows? Nowadays, they diagnose the kid with something and give them some drugs, or better yet, counseling to settle him down. Schools have made some great progress on that front, for sure. Jessica Simpson may have seen a Fit Room in her days at school. She grew up in the 1990’s in Texas alongside her less-talented younger sister, Ashlee.


8 Ryan Gosling

via Pinterest

Do you ever have one of those days when you just want to disappear? Looks like major A-lister, Ryan Gosling was trying to do that in this shot. Either that or he was auditioning for a role in Harry Potter and he brought along his own Invisibility Cloak. Ryan is looking pretty young in this shot, which was probably taken back in the Notebook days. He’s come a long way, and his career couldn’t be any better. But he still takes weird photos. It must be what he does for fun. He seems like the type of guy who might have a hard time taking himself seriously. There are odd pics of him using Emma Stone’s hair as a mustache. In another even stranger pic, he uses her hair as the hair on his head. In yet another shot, he is brushing Steve Carell’s face with a makeup brush and failing. Sabotaging photos seems to be a hobby of his.

7 Natalie Portman

via BuzzFeed

We’re not quite sure what is going on in this one, but it certainly is embarrassing to such a proper star like Natalie Portman. She looks young and very naive in this shot, which appears to be some type of weird peek-a-boo game. Either that or she’s trying too hard to act hot and has a look on her face that is not attractive. Plus, the whole shoot looks so low-budget. What is that blue background behind supposed to be? And her hair and makeup look nonexistent. Portman has come a long way since this shot. Current photos of her are all money. She looks expertly coiffed and perfectly poised. She just drips wealth, power, and success, which is such a contrast to this mousy little pic. Look for her next movie, Annihilation, to hit theaters this February. It features Portman as a scientist on an expedition who discovers some horrific freaks of nature.

6 Halle Berry

via Pinterest

This shot was taken from a series of photos, which documented Halle’s acceptance of the Harvard University Hasty Pudding Award. There are several shots of Halle acting like a total goofball. In one shot, she has her arms outstretched like she’s dancing. In other shots, she is crawling on the ground with her butt up in the air. In this shot, she is hoisting up her chest with an odd, hard-to-read expression on her face. She must regret her behavior in these photos. Although the Hasty Pudding Award is met with a goofy stage performance and a bunch of awkward jokes, there was no reason for Halle to behave quite like this. Surely, she saw the photos afterwards and felt regret. The Hasty Pudding Award is one of the oldest theatrical awards in the country and is awarded to a man and woman in the entertainment business annually. Harvard thinks it's so cool.

5 Leonardo DiCaprio

via Image directory

Who in the world is this? At first glance, it likes like some young YouTuber or a Disney promo for some awful new sitcom. Nope, it’s none other than a young Leo. And, man, this dude has got to be regretting this one. The question is, who convinced a usually reserved Leonardo DiCaprio to gel up his hair so much that it looks like he got electrocuted? Dude looks like either Johnny Test or Eraserhead. I think I know who convinced him to take this shot. I bet there was a hot little female photographer or makeup artist who gave him a little smile and flirted with him. After all, if Leo is a superhero, we all know that women are his weakness. The dude is now a serial dater, and this is back before that started. Leo’s next project is rumored to be The Black Hand, a true story about cops and mafia in New York. Leo plays the lead cop and so-called Italian Sherlock Holmes. Can't wait.

4 Jennifer Garner

via jollywollywood.com

This has got to be one of the most awkward poses there is. The furniture is weird, the outfit doesn’t match, and the posture is just crazy. Maybe this could have been some type of high fashion, but it’s overly s*xual. She has that smokey-eyed come-hither look that only graces the pages of lad mags and doesn’t get anywhere near art. This shot is also very out of character for the now rather conservative Jennifer Garner. Now, Jen is all about raising the family and trying her best to get Ben Affleck back on the straight and narrow. She surely doesn’t want her daughters to see shots like this. She doesn’t look pretty nor hot. It’s just kind of strange. Maybe if it were cropped better, it could be less offensive, but as it shows here, it’s a WTF.

3 Ryan Reynolds

via animalpicturesociety.com

This is an awkward shot. Not only is the staging, lighting, and wardrobe a little off, but for crying out loud, those props! What is the idea here? And to make it even worse, just look at Ryan’s face. He knows that this is awkward, which makes it more awkward. Maybe the photographer was trying to be funny, but it’s not quite into that zone yet. It fell flat somehow and is just plain odd. The beautiful young lady in the shot is none other than Sandra Bullock. The pair shot this photo when they were promoting their film The Proposal in 2009. Although the film was rated PG-13, it included a lot of physical comedy, which took place with both stars completely in the buff. In a post-movie interview, Ryan was asked, 'What’s something that many people don’t know about Sandy?' and he said, “She looks terrific naked.” The two had some great chemistry, but ended up marrying different people in real life.

2 Tiffani Thiessen


So, Tiffani may not officially be on the A-list, but for many of us here at The Richest, Kelly Kapowski is second to no one. And here she is deciding to wear nothing but a large floppy hat. Surely, she thought this was a bad idea when she picked up the hat. Is this something Kelly Kapowski would do? Wouldn’t Mr. Belding be a little embarrassed by this decision? There are many photos like this of people in the buff, hiding themselves behind an object, and it’s really not attractive; it’s silly. It’s like the scene in Austin Powers when he hides his junk behind a bowl of fruit or when Charlotte McKinney strutted in the buff through a farmer’s market and hid her melons behind some cantaloupes for a Carl’s Jr. commercial. The whole idea has been around since Adam and Eve hid their junk behind some fig leaves. Ideas that old are usually very cliche.

1 Sandra Bullock

Speaking of Sandra Bullock and Ryan Reynolds, here’s Sandra again in another awkward shoot. Many of these celebs seem to fall into these traps with photographers. We’re not sure if the photog is super charismatic, or maybe the actors themselves come up with the terrible ideas. For instance, who was responsible for this outfit? The hat looks so strange, the necklace is whack, and the sunglasses are crap. The jeans were obviously out there, and where is her top? The way she is angled isn’t even that attractive. How can you shoot a beautiful woman with no top on and have it not be attractive? This is truly a disaster. Her laughter is probably out of control because she just realized she made a huge mistake that she will regret for the rest of her life.

Sources: Buzzfeed, Izismile, Wikipedia, IMDb


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