Totally Awkward Magazine Covers People Regret Ever Doing

Runner’s World: 1980s Cringe

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It can be fun to look back at retro magazine covers and this one from April 1980 is one of the funniest. The whole setup just screams of the 80s. From her feathered hair to their short shorts, this was the epitome of popular athletic gear at the time.

Not to mention her awkward leg left and his deep lunge. These two look like they’re ready to jog right off the cover of the magazine. This publication has a reputation for featuring cheesy photos and we love that they made it at the top of this list of awkward magazine covers.

Interview: Jennifer Aniston’s Weird Stance

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Jennifer Aniston is a superstar that seems like she could do no wrong. So, it was quite a shock to see her strange March 2020 cover for Interview magazine. The actress stood in some sort of squat onto a desk while wearing nothing on the bottom but a pair of undies and thigh-high boots.

While she still looks gorgeous, the awkward stance got everyone all riled up. The photo set social media ablaze with criticisms about the cover. Some were shocked that she posed in such a suggestive way, while others compared her to a broken doll in a toy box. Ouch!

Harper’s Bazaar China: Sarah Jessica Parker’s Photoshop Fail

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Sarah Jessica Parker’s name goes hand-in-hand with fashion, thanks to her role as the stylish Carrie Bradshaw on the hit show Sex and the City. While we’ve seen her on the cover of many magazines, she looked a bit off on the March 2013 cover of Harper’s Bazaar China.

They Photoshopped her face so much that the actress was barely recognizable. From her crazy smooth complexion to the intensity of her blue eyes, there’s no way a person could like that without poorly executed retouching. Poor thing doesn’t even look human. We’re not sure who they thought they were fooling.

People: Betty White’s 100th Birthday Cover

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Fans fell in love with Betty White from her time on the show Golden Girls and in movies like The Proposal. In honor of the actress turning 100 years old, People magazine ran a cover story celebrating her life in January 2022. In a heartbreaking turn of events, White passed away on December 31, 2021, just 17 days shy of her 100th birthday.

While fans mourned the loss, one awkward situation popped up. People‘s cover story had already hit the newsstands. While it may have seemed like poor timing, it was actually comforting to see her smiling face after her death.

Time: Virtual Reality

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Palmer Luckey, the inventor of the virtual reality headset Oculus Rif, appeared on the August 2015 cover of Time magazine. At the time, VR was a new technology and while it was exciting to have Luckey featured, the cover was roasted big time by readers. 

For starters, he was shown leaping in the air with no shoes on, in an almost childlike way. Then, people were outraged by the unrealistic beach seen behind him. Social media blew up with pictures of him Photoshopped in front of various scenes. Unfortunately for Time, the whole thing was a huge flop.

Runner’s World: Stretching Out

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We take a look back at vintage magazine covers to find this gem. Runner’s World magazine features stories geared toward health nuts and this cover from February 1981 was focused on stretching exercises for the groin, hence the awkward pic of people stretching.

This photo is a celebration of all that was hip in the athletic fashion world in the 80s. From the stripes down the side of the running shorts or the baby blue New Balance shoes, this was such a popular style then. We’re so glad that a magazine cover like this exists because it’s like a weird time capsule.

Time: Breastfeeding Cover

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Time magazine caused quite an uproar with the cover of their May 21, 2012 edition. The photo featured a woman breastfeeding her 3-year-old son while he stood on a chair. The headline read: “Are You Mom Enough?”

The controversial cover brought attention to attachment style parenting, but many readers were shocked to see the photograph of a young child suckling on his mom’s chest. People found the image to be too extreme, and it opened a debate on the culture surrounding breastfeeding and appropriate weaning times. Either way, it created quite an awkward moment for newsstands.

Hello!: The Emo Duke Of Cambridge

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Prince William landed the February 22, 2010 cover of Hello! magazine to the amusement of everyone. The Duke of Cambridge appeared to look a bit different than he normally did in this now-famous photo. It wasn’t just his casual attire that caught everyone’s attention.

Someone in the styling department decided that he’d look better with a head full of black hair instead of his signature thinning blonde hair. It was such a stark contrast that the cover became the butt of many jokes. Which is sad, because he looked really cute with dark hair. Maybe he should consider making the change.

Parents: Unfortunate Photo Placement

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Parents magazine is a reputable publication that gives moms and dads parenting advice. That makes this unfortunate cover from April 2005 even funnier. Thanks to the placement of the woman’s noggin, the masthead was transformed from “Parents” to a certain part of the male anatomy.

This is a case where the cover editor had a bit of explaining to do. We’d love to be a fly on the wall during that meeting. They literally had one job and totally failed at it. Thank God they did, because now we have this hilarious magazine cover to immortalize in all its glory.

Marie Claire: Alien Eva Mendes

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We can’t help but wonder what the folks over at Marie Claire were thinking when they edited this photograph of Eva Mendes for their March 2021 cover. We don’t mind that it looks like they stuffed her into a bustier with candy glued on it.

We do take issue with the fact that they totally morphed her right arm and messed up her face with Photoshop. This woman is so stunning, why did they even think they needed to retouch her photos? She looks like an extremely glamorous other-worldly being. This is just another example of how the media distorts natural beauty.

Time: Prince Harry And Meghan Markel Airbrush Fiasco

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Prince Harry and Meghan Markle graced the cover of Time magazine’s “100 Most Influential People” on October 4, 2021. Markle wore a white power suit while Prince Harry went for an all-black look. It wasn’t their fashion choices that got everyone talking, though.

Social medias lit up with comments roasting the cover because their faces were so heavily airbrushed. Many people thought that the image looked like CGI. Other readers commented that it looked like Markle wore the pants in the relationship because of the way Harry hid behind her. Regardless, this cover is pretty much as awkward as they come.

Filmfare: Born Again

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This next item on this list is pregnant with possibilities. The April 1988 cover of Filmfare was a bit of a head-scratcher. It featured Bollywood star Shah Rukh Khan posing as a pregnant man, and by the looks of his bump, he was about to pop. 

Who came up with this concept? We get that it goes with the headline “Born Again” that appeared on the cover, but it’s a bit strange. Oh well, in this day and age, anything goes. Who are we to judge? More power to you, Mr. Kahn. This cover was ahead of its time in the 1980s.

WebMD: Lollipop Head

Olivia MunnThe Daily Edge

Olivia Munn was the victim of an epic Photoshop fail when she was on the January 2016 cover of WebMD. The retouched image not only made her head look much larger than her body, but her chest looked a bit wonky as well. We’re not sure how this one made it out of the editing room.

What makes the cover even more insulting was the headline, “Olivia Munn on self-acceptance and success.” The article discussed that she struggled with her body image. Way to go, WebMD! We bet Munn wished that she never agreed to be the cover after that unfortunate mix-up.

People: Poorly Placed Photos

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People magazine is known for publishing the dirt about all of our favorite celebrities. Every now and then, the publishers like to put out a cover story that features everyday people. Like this one, from January 2016, which was about real people and the diets that helped them become half their size.

While we applaud them for trying to reach out to the common man, it appears like someone in the editing department forgot to wear their glasses. The poorly placed photos transformed their name from People to Poopie! That’s one hilarious mistake, if you ask us.

InStyle: The Missing Wrist

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There’s no denying that Carrie Underwood is a talented artist and a beautiful woman. She must have been so excited when she was offered the chance to be on the cover of InStyle magazine. The December 2010 issue featured the lovely singer in a glam dress.

There was just one problem. In yet another Photoshop fail, editors somehow made her right wrist disappear altogether. She’d have to be a contortionist for her arm to be able to bend in such an unnatural way. She must have been so embarrassed to appear disfigured on the cover of a magazine that covers Hollywood style.

W: Demi Moore’s Photoshop Nightmare

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Demi Moore starred in huge hits in the 1990s like G.I. Jane and Indecent Proposal. While her acting career has taken a backseat to family, the actress still pops up at red carpet events and magazine covers now and again.

She somehow seems to defy age and looks more beautiful the older she gets. However, her 2009 cover for W magazine had readers scratching their heads. It appeared like her left hip had been Photoshopped. Moore took to Twitter to defend the photo, claiming it wasn’t retouched. Yet, it’s pretty obvious it was smudged a bit.

Men’s Health: Zac Efron’s Bionic Arm

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Zac Efron found fame when he starred in the popular show High School Musical. He’s all grown up now and loves to hit the gym. Men can be victims of botched Photoshop, too. Take this cover of Efron on the May 2021 edition of Men’s Health.

While it’s a nice photo of him, there’s just one problem: his left arm looks totally jacked! While it’s entirely possible for him to have a chiseled physique, that arm looks way too bionic for reality. He pretty much looks like The Terminator. Not that we’re complaining or anything.

Sassy: Not So Sassy

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Sassy magazine was made for Gen X teen girls in the 90s and was known for being cutting edge when it came to fighting beauty standards. So, it’s no shock that they would feature a total nerd on their cover along with the headline “Our beginner’s guide to makeup.”

We don’t mean to be mean, but this girl with huge glasses and braces was a far cry from your typical cover girl. Not to mention her red tuxedo jacket and bow tie. This has got to be a joke because it’s just too funny to be a real magazine cover.

Glamour: The Disappearing Arm

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Kristen Stewart exploded to fame when was cast as Bella Swan in the Twilight movies. It seemed like she was on the cover of every magazine during the promotion of all 5 films. The “it girl” normally looked cute and glam in every photo taken of her at the time.

However, Glamour magazine featured her on their November 2011 cover and the whole thing was a Photoshopped mess. Readers were quick to call out that they had completely edited out Stewart’s left arm, which seemed haphazardly placed behind her knee. It didn’t help matters that she sat in such a strange pose.

Elle: The Flamingo

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Kylie Minogue is a gorgeous Australian singer and actress. She’s always on the cutting edge of fashion, so it’s no wonder that Elle magazine featured her on the cover of their January 2013 edition. They showed a photo of her standing in a chic mini dress and spiked high heels. 

The usually flawless beauty was yet another victim of bad Photoshop when they cut out part of her left leg. The poor thing ended up looking like an awkward flamingo. Where did the back of her leg go? It’s a mystery and we may never know the answer.

Ebony: A Bit Overdressed

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Mariah Carey and Nick Cannon posed for the January 2014 cover of Ebony magazine. They were called out for being totally out of touch and posing in a swimming pool in evening wear. Carey plunged into the water wearing a red gown with black heels, while Canon wore a suit.

The whole thing looked forced and slightly absurd. Of course, the irony is not lost that the headline talks about secrets to making your love last, and these two divorced only 2 years after the magazine was published. This cover just did not age well at all.

Bloomberg Newsweek: All About Perception

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Bloomberg Newsweek magazine covers the latest trends in technology and finance. Readers turn to them to find an in-depth analysis of current events and get financial tips. It’s a serious publication for serious people.

We just couldn’t resist adding their July 2013 cover, which featured a businessman standing before a rather phallic graphic to represent the “Hedge Fund Myth”. Kudos to whoever designed this hilarious image, because it certainly caught our attention. Depending on how you look at it, this guy was either very excited or totally turned off by hedge funds. Either way, this cover is priceless.

Rolling Stone: Historical Mistake

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Julia Louis-Dreyfus played Vice President Selina Meyer on the series Veep for 7 seasons. So, it made sense that she’d pose nude on the cover of Rolling Stone magazine in 2014 with a fake tattoo of the American constitution printed on her back. What seemed like a clever idea ended up being an epic failure. 

The actress was called out because John Hancock’s signature appeared on the lower left side of her back. This caught the attention of history buffs because John Hancock signed The Declaration of Independence, not the Constitution. Who says the historical accuracy is important, anyway? Sheesh!

Joy: Taylor’s Unrecognizable Face

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Taylor Swift is a superstar who little girls look up to. She’s won 11 Grammys and has recorded huge hits like “Shake It Off” and “Bad Blood”. The singer has graced the cover of many magazines, but this one takes the cake.

Swift was featured on the front of a Russian magazine and looked more like a victim of bad Photoshop than the icon she is. They airbrushed her face to the point that you can barely tell that it’s her at all. No one has skin that smooth in reality. That photograph couldn’t even pass for a Taylor Swift lookalike.

Vogue: The Longest Arm

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At first glance, this March 2017 cover of Vogue looks like a celebration of diversity, showing models of various ethnicities and shapes. The cover featured Liu Wen, Ashley Graham, Kendall Jenner, Gigi Hadid, Imaan Hammam, Adwoa Aboah, and Vittoria Ceretti standing in a huddle. Yet, a closer look reveals that the magazine pulled some Photoshop shenanigans.

The publication was blasted for editing Gigi Hadid’s arm to extend it to cover plus-size model Ashley Graham’s waste. While Vogue never confirmed or denied the accusations, Hadid would have to have a freakishly long arm for them to have not touched up the photograph.

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Author: Hailey Warren