Every family photo album has its fair share of nostalgic bloopers, the Kardashian’s family album is no exception; only their family blunders are cast out and exploited for our viewing pleasure. These photographs have pinpointed the most “cringe-worthy” images of America’s most talked about family. Most commonly known for their extravagant wardrobes, jaw-dropping allure, and breathtaking beauty, these photos capture precisely none of those things. To the untrained eye most photography can be multi-faceted and more complex than one might initially think, these photos require nothing more than a hearty sense of humor, and a friend or family member to enjoy them with.
The Kardashians are widely considered America’s most beautiful and controversial family in popular culture, these photographs provide a unique glimpse into the family’s more humane side, proving what seems to be overlooked when we think of the Kardashians; they are human. From Khloe to Kim, Kylie to Kendall, the ups and downs of relationships, pregnancies, television tragedies and controversial life choices, the Kardashians have provided our popular culture with a seemingly endless supply of material. As we flashback to the lives of these folks, take solace in the fact that these days have come and gone. Grab your popcorn, grab a buddy, and enjoy the show!
25. Is That A Bed Sheet She’s Wearing?
Besides the fact that Kim looks less like a supermodel and more like pregnant soccer mom wrapped in a bed sheet, everything else with the picture is par for the course. However, the spotlight and eternal glory that has cast itself over the family tree should be cause to pause for Kim each and every time she leaves her home.
If this outfit was indeed planned and destined for success, well, the actuality of its revealing left more to be desired than she (or Kris) could have hoped for. Photographs such as this one are bound to leave Kim’s mother Kris scrambling for the delete button. Of course pregnant mommies around the world cannot be expected to slim down when expecting, however Kim Kardashian has a more than average attraction from paparazzi and media alike.
24. Virgin Mary…Really?
Kim Kardashian’s outfits have hit an all time high, or in this case all time low. The see-through black dress is par for the course for the Kardashians, however the Virgin Mary patch is not only offensive, but a horrible fashion statement. It’s images and outfits like these that justify the sometimes brutal criticism the family receives (warranted or not).
From all accounts, we haven’t seen the Virgin Mary starting any fashion trends as of late, but we could be on the brink of a religious breakthrough, likely we aren’t though. More likely is controversial uproar from religious bodies around the globe, and for good reason. Dresses like this are exactly what Kris Jenner is trying to avoid, we can only imagine her reaction to photographs such as this one.
23. Fashion Faux-Pas…
Every once in a while a superstar rocks the red carpet outfit that absolutely leaves us in awe, this is not one of those times. Coupled with a questionable at best haircut, the usually stunning Kylie Jenner is leaving much to be desired with the entire ensemble. With a family that personifies beauty and style, it’s a rarity to come across an image of a Jenner/Kardashian that puts a new definition to disaster. Kris Jenner might very well be trying to bury this as we speak, as a matter of fact she most likely tried to do everything she could to have her daughter avoid this fashion faux-pas. Like the rebellious daughter she was, (and independent mind you) she tackled the paparazzi with this wardrobe on, so more power to you.
22. Call The Wham-bulance
This picture probably looks familiar, it is by far one of the most frequently used pictures for memes and internet humor alike. Even if you don’t know much about the Kardashians, chances are when flashed a photograph of Kim Kardashian she is doing one of two things; looking devious and sexy, or looking like this.
Whether Kim’s income has come from moral (or less than moral) means, photographs like this one can’t help but portray the image of childish superiority. We all have that one friend, who when denied his/her way, throws an absolute temper tantrum. Either way the internet has capitalized in glorious fashion, capturing an image that would make any mother cringe in disappointment.
21. The Pepsi Chainsaw Massacre
This Pepsi commercial of Kendall is quite baffling. Perhaps it’s the fact that a quintessential “model” figure is promoting a beverage that is known to give you the reverse affect, or because Pepsi has used another commercial to attempt to solve our political and social quandaries through their product. The typically stunning Kendall Jenner just simply does not have her usual vivacious smile and personality in this image, and the ratings reflected that folly. The commercial received such flack that you likely didn’t see it airing on television either. After a short shelf life over the air, Pepsi pulled the commercial after receiving brutal condemnation for its resemblance to the highly controversial “Black Lives Matter” campaign. One thing is for sure, Kris was shaking her head just like the rest of us.
20. The Double Chin Double Take
When someone thinks of the Kylie Jenner the last image that formulates in their mind is probably a double chin. In all fairness the only time you ever really catch such an unfortunate circumstance likely comes from a string of bad luck and unfortunate timing from a photographer. Nevertheless such photos emerge at superstars’ expense everyday, and the Kardashian/Jenner family is no exception. Whether the result of this photograph was bad timing, and just an oblivious superstar, we have put it on display for your viewing pleasure. America’s most watched and critiqued family often reminds so many of us how human they truly are, and photographs like this help to minimize the collective ego of the family, chipping away a little each time.
19. Letting Loose Off The Goose
If this picture doesn’t scream High School Prom, were not sure what does. Try to disregard her apparent death lock grip on the bottle, the viscous distaste of all things alcohol, and such bitter disgust she can’t even keep her eyes open. We’ve all been there, right? Images like these cannot be her mother’s first choice for Christmas cards, let alone family album worthy. This picture might spark some memories of your first high school party – you know that one you woke up and couldn’t remember? It can be hard to wrap your head around the notion that superstars such as herself allow themselves to be flashed in such disadvantaged poses. Nevertheless said images have been captured for our viewing pleasure, and we can’t get enough!
18. Kendall What Are You Most Grateful For?
Kendall Jenner may be the youngest, but cringe worthy photos like this have to have her mother Kris scrambling for solutions to rid these images from the internet, and our minds. The rebellious streak and wild-child stamp are riddled all over this image and speak to “tutelage” Kendall may have (or not) received from her older siblings.
If history is any indicator, this won’t be the last controversial photograph in Kendall’s future, but hey, all publicity is good publicity…right? To be fair, with beauty like hers that phrase might actually ring true. Either way, with good publicity or poor publicity Kendall must be earning extra coal in her stocking for Christmas this year from Santa Claus with racy images such as this one.
17. The Picture….It BURNS!
This image of Kim Kardashian seems innocent enough, she may have even done it herself for the laughs, and if it was laughs she was looking for, we are here to accommodate. Like several pictures in our lineup, this particular photograph has “Cringe-worthy” written all over it. There’s no amount of makeup that could cover up those sunburns, and no amount of hypnosis to erase this image burned in all of our minds. Sunburns happen to all of us, but unlike most of peons, Kim’s every move is under neighborhood watch. More power to Kim for clearly embracing the third degree burn heard around the world. Kris Jenner most likely has a burn idea of her own in mind, including a lighter and a tank of gasoline!
16. Frankenstein Pose?
Kylie Jenner has landed herself quite a few times on our list of disaster photographs, the simplest explanation is that she is a goofball. The more refined explanation is that paparazzi attach to the star family like leeches and are bound to capture images such as this one. Most of the images we have included involve oblivious gestures and oversights by the second youngest of the star family.
Here she is pictured at the mercy of a horrifically timed cross-eyed Frankenstein pose, and we don’t think that this is the newest fashion pose. One can only imagine that this photo was snapped at the worst possible time, and we can venture to guess that Kylie and Kris both are dying to have this image removed from American psyche.
15. The Most “Cringe-Worthy” Photo Goes To…
As if her makeup artists didn’t already have their hands full, Kim has got them working overtime. Pictured here is Kim’s longtime Makeup artist Mario Dedivanovic applying body makeup to Kim’s rear end. If you have any insight into Kim’s assets, then you can probably guess that there is a lot of surface area to be covered on her backside.
The always innovative Kim Kardashian has pioneered a new kind of badly timed photos, this one while receiving makeup from an over-attentive male. In all honesty who is looking at the back of her thighs? Just in case you catch a glimpse, there will certainly not be a tan line, and perhaps a lot of oil and bronzer. It’s not hard to tell why Kim’s mother Kris has tried to set aflame this photo numerous times in her nightmares.
14. The Old Khloe
Out of the entire Kardashian/Jenner family Khloe has had the greatest transformation. Once viewed as the proverbial black sheep of the family, she has made a drastic and remarkable transformation over the past 5 years. Photographs such as this one serve as a reminder to her (and her mother) just how far she has come. Lined up side by side with her sisters, in years past, could be quite demoralizing, as seen here she was considered overweight (by supermodel standards) and less attractive than her counterparts. An image of what she looks like today allows pictures like this to do justice to the trials and tribulations she has overcome as a famous figure, and as a hard working woman. Nevertheless photographs like this one probably end up as paper airplanes to the Kardashian mob.
13. Walk Of Shame?
Young Kylie Jenner, as seen here, with a rebellious streak of turquoise hair, crawls out of her car entirely unaware that the paparazzi was plotting to ruin her morning. It appears that superstardom lands you an upgrade from the standard “walk of shame”, to the more refined “drive of shame”. With her hair in knots, an unenthused Kylie Jenner glances effortlessly and carelessly and drags about her day. Kris Jenner has done her best to uphold a high standard of living for her entire family, and oblivious oversights from Kylie must be enough to drive her wild. At the end of the day Kylie is her own individual and is entitled to make whatever accessory changes to her body she wishes, unfortunately for her we will be there to judge her every move.
12. Sinister Stare Down
This insidious glare is enough to make us all wish it didn’t happen, let alone Kim’s mother Kris. The combination of bleach blonde hair, pasty white makeup, and sinister stare down share a remarkably close resemblance to Aladdin character Jafar. Photographs such as this one make us all question how by all accounts this gorgeous superstar could end up with a resulting snapshot such as this one. We think Kim might be scrambling to bury this photograph faster than her mother Kris! The ominous undertone of this photograph portray the exact opposite of what Kris Jenner has cultivated over the years, it would appear that Kim is purposely trying to undermine all of her mother’s hard work!
11. No Makeup…No Problem…Right?
We have come to expect that the Kardashian Divas will always look like super-humans who appear to be able to capture our attention no matter what they are doing. This image has certainly captured our attention, but probably not for the reason that Khloe Kardashian is accustomed to. Khloe has widely earned her title as the most “laid back” of the Kardashian crew, and this picture certainly can attest to such an accusation. No matter what the reason was for Khloe’s lapse in judgement, we can probably guess what Kris’ reaction was; less than satisfied. Another reminder etched into our brains about the seemingly incredible transformation Khloe has made. By all accounts she could be considered the sexiest of the Kardashian clan, and for good reason, she earned it!
10. Is That A Rearview Mirror On Her Face?
Despite the fact that Kim’s glasses resemble a hi-tech rearview mirror, her body captured in this photograph is a rare depiction of a body we aren’t necessarily accustomed to seeing when we look at Kim Kardashian. Typically speaking, when she is wearing a bikini and sunglasses, we envision Gucci sunglasses, a dark tan, speak frame with voluptuous assets to accompany a shockingly skinny figure. This picture deviates from that norm in almost every aspect. The large hoop earrings collaborate with the less than stellar bikini selection to create an astonishingly lukewarm response. Kim and Kris are probably racing each other towards a flamethrower or a dumpster to rid the world of this image as fast as they can.
9. Deep Purple…
The eyeshadow alone says it all, the shellshocked look on both Khloe and Kourtney’s face says even more. The young and naive future superstars probably had no clue that this photo would circulate decades later, so in fairness to them we understand the oversight. This flash to the past etches an image in our mind of what these two used to look like, needless to say things certainly have changed. The rosy red cheeks coupled with bright purple eyeshadow is certainly one way to play it… we are going to go out on a limb here and venture to guess the makeup artist for this fiasco was fired immediately afterwards. Kris may have had something to do with his/her release as well.
8. Kourtney….A Belieber?
Kourtney and Justin Bieber rumors have circumnavigated the globe several times over since their original siting several years ago. Justin Bieber has insisted that their relationship is entirely platonic, but we are not sure that we believe him. They have been seen together numerous times over the years but Justin insists that “He has known the family for years”, and that he “Thinks it’s cool she’s older and she’s hot”. Certainly the numerous times they have been seen together explains more than just a cordial friendship between superstars, and with relentless speculation on our part rumors are destined to tumble into larger than life accusations. Needless to say Kris Jenner cannot enjoy constant speculation about which new pop star her daughters are intertwined with.
7. An Unwanted Guest
What would a famous pop-culture figure be without the classic nip slip shot? Unfortunately for Khloe, that exact thing happened, on live television. Side by side with her sister Kourtney, airing a live broadcast of Fox’s former hit series Fox and Friends, she was caught “slipping” so to speak, and was never allowed to live down the shame. When asked about the blunder Khloe responded with pure class, “I had a nip slip and I loved it!”, making light of a semi-serious occasion. No mother wants to see an image of her daughters having to deal with such heat from the public conscious, so it’s no wonder that Kris wants to erase this photograph from public knowledge as fast as she can, good luck!
6. The Ray-J Fiasco
The romantic episode with pop-singer Ray J is probably something that Kim may want to forget about more than Kris, matter of fact I think we might all like to rid those memories from our collective past. The controversy that emerged from their “sexual encounters” was most likely enough to make her vomit up her caviar and champagne. These blasts from the past are enough to make any of us uneasy, imagine how Kim must feel when she glances at a photograph such as this one? We all have those ex-lovers in which a simple reminder is enough to drive us insane, this nightmare is like our past-lovers on steroids. Some of these nostalgic mementos need to stay right where they are, in photographic purgatory.
5. What Are Those?!
As if having a young daughter sucked into the family vortex of fame isn’t bad enough, try having that same daughter shot into superstardom while she is still figuring out who she is. Stunts like having one’s nipples pierced are much more common than one might initially think, however cases such as Kendall Jenner are cast out into public opinion to be eaten alive like a piece of krill to a killer whale.
Kris has to juggle 5 daughters while dealing with a life of her own, we can only imagine how hectic a day in the life of Kris Jenner must be. Pictures and scrutiny that photos such as this one attract, must drive Kris Jenner to her wits end, which is why you can probably find her searching for a headstone to bury this picture under.
4. Better Luck Next Time Kendall…
We all get caught from time to time in a not so advantageous vantage point of our double (or triple) chins. The vast majority of us, however, are not mega stars who face intense scrutiny under society’s magnifying glass. Call it bad timing, call it a stroke of bad luck, but this photograph of the youngest member of the Kardashian wolf pack could not have flashed at a worse time.
Kendall will have the rest of her life to live and learn the best way to avoid photographic disasters such as these, but if her sisters’ pictures on this list are any indication, she might want to steer clear from their advice. If this image proves anything, it is that even the skinniest model figures can create the notorious double chin, so don’t feel so bad about yourself the next time you catch yourself in one of these nightmares.
3. Kim….Not Again?!
A mother’s greatest fear might be her daughter having an unplanned pregnancy, her second greatest fear might be finding a nude photo of her daughter. It’s hard to imagine that a former victim of a sex-tape scandal gone viral would find herself caught in another racy photograph online. In all fairness this image looks like a calculated pose undeniably attracting attention; but it still makes you wonder. Of all the publicity that has emerged (positive and negative) it definitely seems to be walking a fine line with the ever controversial image of Kim in the public eye. For the reasons just mentioned, and for countless reasons concerning a mother and her daughter, we believe Kris Jenner has been fearful of such photographs creating backlash on her prized image, so we think it’s fair to believe she would be content with this image falling off the face of the earth.
2. A Little Twerk Never Hurt Nobody…?
With Kim Kardashian’s background it might not surprise you that a picture of her pole dancing has made it onto our list. The only catch is that this picture was taken after she had her child with hip-hop star Kayne West. One of the main reasons Kim’s mother Kris might be caught with a shovel digging a photo sized coffin with this picture in her hand is simple; she joined in on the fun! Both mother and daughter were grinding, twerking, and letting it all hang out on their hit television show, Keeping Up With The Kardashians. As a spur of the moment activity, pole dancing might squeal its way into some of our daily lives, but a well constructed highly popular television show does not seem the time nor place to conduct such a scandalous hobby.
1. Khloe And Lamar Odom
Pictured here, Khloe (and Kris) probably wants to forget this chapter of her life just as bad as the rest of us. After the controversial relationship with former basketball star Lamar Odom, these images surfaced at a time when the ex-Lakers star was battling an intense drug-overdose, in which he was inches from death. Since the overdose and subsequent hospitalization Khloe has made public statements wishing the best for her estranged partner.
Shortly after her brief stint with Odom, the two split and have since parted ways. Kris and Khloe have since separated themselves with Odom, who is battling a severe addiction to crack cocaine. Lamar has since recovered from his brush with death, but the future remains unclear on his battle with addiction.