You know Kylie Jenner; she is the youngest of the Kardashian-Jenner clan and at 19 years old, she has already solidified herself as the wild, sometimes bratty, and pretty much talentless sister. She also has to compete with her sister Kendall, who is burning up the modelling scene with runway shows and fancy photo shoots. Kylie has done a bit of modelling too, but she just isn’t as gifted in the looks department as her sister. That’s okay though, because Kylie has other activities to pursue. For example: makeup. There is no denying that Kylie has had a major lip transformation over the years, and she even released a line of Kylie Jenner Lip Kits (more on that later.)
Even though she is trying new things and trying to branch out, it seems that Kylie still harbours some poor self-esteem. The most selfie-indulgent of the Kardashian-Jenner sisters, Kylie seems to be very attention-seeking and needy. Plus, there is that whole on-again, off-again relationship with Tyga (we’ll talk about that later, too.) Yet Kylie still has loads of fans who keep up with her every move, so here are a few things that her fans may want to just ignore or erase from their memory (if they can!) Good luck trying to forget about Kylie’s most embarrassing moment, or how her entrepreneurial ventures panned out.
15 Her Horrible Karaoke Skills
On several occasions, Kylie Jenner has tried her hand at karaoke, and each time is has been...well, not too good. One example was when she was at her sister Khloe’s birthday party. Kylie did a karaoke duet with Blac Chyna, which was actually pretty surprising, considering that Tyga is rumored to have broken up with Blac Chyna in order to get with Kylie. Everything looks fine and dandy in the video though! Another instance in which Kylie was howling away was in a public bathroom, where she and a friend were singing together. A stranger walks in, and the two girls suddenly stop and look really sheepish. Awkward!
14 She Tried to Wear a Dog Collar
Everyone has been embarrassed by their parents or grandparents at some point, and not even Kylie Jenner is immune. After all, her mother is Kris Jenner, a mom/manager who is just as flamboyant and raunchy as Kim and Khloe Kardashian. If you watch Keeping Up With the Kardashians, you may have seen the episode in which Kylie goes shopping with her grandmother. While they are out and about, they go shopping for a cute dog collar for Kylie’s pup. Then her grandma sees a particular collar that she likes, and she muses that it would make a great necklace for her granddaughter. Oh no, she is not going there, is she? Yep. Grandma tries to put the dog collar on Kylie, much to her granddaughter’s chagrin. The scene was cut out from the Keeping Up With the Kardashians episode, but you can find it online! At least they have grandma to keep them grounded.
13 Poor Product Endorsement
The Kardashian and Jenner sisters are known for promoting certain brands, and there are plenty of companies that come to them for crucial product placement. Who hasn’t seen the fit tea and Calabasas salads that they eat all the time on Keeping Up With the Kardashians? As for Kylie, she was trying to promote a new self-tanning product, but the selfie she took was a bit off. In the selfie, Kylie is posing for the camera in front of a mirror. The photo shows the teenage celeb in a sleek black bikini (and the product she is promoting is sitting right next to her, blatantly leaning against the pillows on her bed). The photo would be okay, except that Kylie missed a huge spot on her upper leg, and the stark white spot on her thigh clearly stands out in the posted selfie. Whoops. Looks like she won’t be cashing out on that campaign!
12 That Her Lips Weren’t Always Plump and Pouty
If we’re being honest here, Kylie Jenner looked so much better before she got all of the cosmetic surgery. Whether you want to call it a “Hollywood makeover” or not, Kylie was actually a really cute girl, and she could have grown up to be a beautiful young woman. Too bad she turned to breast augmentation, a rhinoplasty, lip injections, and more. Now she looks more like an inflated version a scary doll than the naturally pretty Jenner sister she used to be. If you go back to 2009, Kylie wore minimal makeup and her lips were thin, but still nice. Then in 2013, her lips started looking bigger, but mostly due to the drawn lip makeup she was putting on. Gotta love that lip plumper! A year later, Kylie’s lips were much more pronounced and looked almost twice as big, which would lead us to the Kylie Jenner Lip Challenge.
11 Called Out for Cultural Appropriation
Cornrows, blackface, and a Yaki ponytail...Kylie Jenner has been in hot water multiple times for her fashion and beauty choices. Her Instagram is filled with selfie shots, some of which include the youngest Jenner daughter wearing sweatpants and tight braids with the caption “Woke up like dissss.” Needless to say, other people took offense and had to call Kylie out on this cultural appropriation. One of those people was Hunger Games actress Amandla Stenberg had some words for her, who criticized Kylie for promoting her “black hair,” but not using her white privilege to make a stand for black lives matter. Another sticky situation that Kylie found herself in was for a fashion photo shoot in which she appeared to be wearing blackface. And at New York Fashion Week in 2016, Kylie was hit yet again for showing up with a Yaki ponytail, which is often used in black braids.
10 Temper Tantrum at a Hotel
Kylie Jenner was denied alcohol for being underage (good on ya, bar staff!) when she tried to order a drink at a downtown Los Angeles hotel. The 16-year-old Kylie went into a childish temper tantrum, and the paparazzi caught it on camera. She was also with her then-boyfriend Jaden Smith, and that just adds more embarrassment to the situation. Anyway, the incident had people calling out Kylie for being a privileged brat and a prima donna like the rest of the Kardashian-Jenner family. Well, that’s not inaccurate, we must say. Kylie was reported as talking down to the hotel staff saying “Do you know who I am?” before storming out of the hotel and deeming is beneath her.
9 Her Relationship with Tyga
Kylie Jenner and Tyga have been in an on-again, off-again relationship for a while now. And it seems that every other headline about Kylie is in relation to her romance with the 26-year-old Compton-born rapper. Kylie and Tyga first met at Kendall’s sweet 16 birthday party, in which Tyga was the main performer. He and Kendall started dancing together for the crowd, and Kylie quickly joined in (she was just 14 at the time.) Three years later, Tyga and Kylie started hanging out, and a month later, Tyga breaks up with his girlfriend, Blac Chyna. Before you know it, Kylie and Tyga are celebrating Halloween and Thanksgiving together, and it’s pretty obvious that they’re a couple. However, throughout the years, Tyga insisted that he wasn’t dating Kylie. In May, they reportedly broke up, but in August he celebrated Kylie’s 19th birthday while on vacation with a group of other high-profile celebs like Gigi Hadid.
8 The Kylie Jenner Challenge
Remember the Kylie Jenner Challenge? Of course you do! This was the beauty craze that teenagers all over the country were participating in. The whole premise and purpose of the stunt was to get plump lips like Kylie Jenner. As we all know, Kylie has gotten cosmetic procedures done to have her lips look like that. Just go back a few years and you will see that the celeb’s lips were much less full and pouty than they are now. Anyway, the Kylie Jenner Challenge involves suctioning a glass cup over your mouth for a minute to inflate the lips. In reality, this breaks the capillaries in your lips and sometimes causes irreversible damage. Oops! Doctors and professionals warned against trying the Kylie Jenner Challenge, and YouTube blew up with videos of foolish teens trying the stunt and then crying about how freakish they looked. The future generation is doomed.
7 7 . This Disrespectful Texting
This is a really bad one that Kylie would like you to forgive and forget. During a moment of silence for slain black teenager Michael Brown, Kylie and her sisters Kim and Kendall were seen texting. Really though, really?! All of the other people in attendance, including Snoop Dogg and Common (who was presenting the next award nominees) took the moment of silence to be quiet, bow their heads, and reflect on the violence and racial upheaval that is pervading our society. Yet it seemed as though the Kardashian-Jenner sisters had more important things to do, like use their white privilege to not give a rat’s ass and continue texting away on their cell phones. This was really disrespectful, and the girls were sitting in the front row of the audience! One of Kim Kardashian’s representatives said that they were not texting during the event, but the rep didn’t offer any alternative possibilities as to what they were doing.
6 She Can’t be Trusted With Birthday Gifts
With Kylie Jenner being well, Kylie Jenner, she is obviously going to get some pretty awesome and expensive gifts for her birthday. This example was no exception. Her boyfriend Tyga gave her a Ferrari for her 18th birthday, and we could already tell that this was going to end badly. The $320,000 car was crashed shortly after Kylie got behind the wheel. She was okay, as was Tyga, who was in the passenger’s seat, but the car sure wasn’t! It turns out that Kylie is a reckless driver, so what was Tyga thinking? The reality TV star got her first driving offense just two weeks after getting her license because she caused a three-car collision, and she has also been cited for speeding and making illegal U-turns.
5 Booed on Live TV
We actually felt kind of sorry for Kylie when this happened. She was with her sister Kendall Jenner at the Billboard Music Awards, and even their brother-in-law Kanye West was in attendance. It was Kylie and Kendall who were set to introduce and welcome Kanye to the stage for a performance. Yet the audience of the awards show clearly did not want to show any love for the Jenner sisters. Almost immediately, Kylie and Kendall were booed as they tried to walk on stage with smiles and sophistication. If you listen closely, you could hear that some people were clapping and cheering, but they were getting drowned out by the hateful noise coming from the other audience members. The sisters kept a winning attitude the whole time, and continued to smile and just get their introduction over with. To make them feel better, Kanye West’s performance was crappy, and many fans were upset that he censored most of the content.
4 Her Boob Contouring Gone Wrong
How embarrassing is this? In an effort to pump up her breasts (maybe to compete with her sister Kim?) Kylie tried to do some boob contouring with makeup, but the result was less than satisfactory. Too bad nobody told Kylie before she stepped onto the red carpet, because the cameras were flashing and getting a clear view of her makeup faux-pas. As Kylie stood on the red carpet and gave a fierce pose for the paparazzi, she didn’t realize that her cleavage contouring was totally off the mark, making her chest look splotchy and uneven. When the photos were published, Kylie must have been so mortified to see that her effort to promote her makeup line took a disastrous turn. It looked awful! What happened was she used some very dark bronzer, and the streaks and lines of the contours were super jarring and extreme when the photographers snapped her picture.
3 She Nearly Fell on Her Face
On more than one occasion, Kylie has had trouble with her high heels. For example, one time she was at a party event with her sisters Kim and Khloe. The 16-year-old Kylie was sporting a mini skirt and matching black blazer, along with some bright teal-blue hair. As the sisters were leaving the event, Kylie was bringing up the rear, and she tripped on the sidewalk, nearly twisting her ankle and falling flat on her face. She had to actually grab onto Khloe in order to avoid falling down completely. The paparazzi cameras flashed and someone let out a shriek. Similar stumbles happened to Kylie in Malibu and during a photo shoot with her sister Kendall. The girl clearly is not too sturdy on her feet! A year after that first stumble, Kylie fell completely on her face while running in the sand with Kendall. Thank goodness that they were on the beach and that they had nice security guards to help!
2 She S**t Her Pants
In a Cosmopolitan exclusive interview, the Kardashian and Jenner sisters (and their mother) sat down with the magazine to talk about some of their most embarrassing moments. And while the other siblings had some pretty cringe-worthy stories to share, they could not compare to Kylie’s story. For instance, Kourtney is apparently a “queefer,” as her sister Khloe describes it. Kris Jenner had sex with her husband Bruce in an airplane bathroom and was called out on the PA system for joining the “Mile High Club.” Embarrassing for sure, but Kylie had actually pooped herself in the Kardashian-Jenner home and left a trail of her poo from the bottom of the stairs all the way up to her room. That’s just plain gross, and as if the public and tabloids really needed more ammo to throw at Kylie and her family, the admission of her poop mistake just put it over the top.
1 Her Lip Product Line
Okay, so there is no doubt that Kylie Jenner had some major work done to her lips. They are way more puffy and pouty than they were a few years ago. And hey, she’s part of the Kardashian-Jenner clan, so plastic and cosmetic surgery is to be expected. Anyway, Kylie was under fire for her Kylie Jenner Lip Kit, a cosmetic brand of lip products that had trouble getting approval from the Better Business Bureau (BBB.) As of July of 2016, the Kylie Jenner Lip Kit has a “C” rating, which is a whole lot better than what the celeb’s been recently dealing with. Customers who ordered the Lip Kits were reporting that their packages took months to arrive, or they arrived with missing items, or not all! This is probably one of the most embarrassing things that Kylie Jenner wants you to forget. The girl just doesn’t have what it takes to be an entrepreneur.