At 22 years old, Kylie Jenner is living that life that so many of us can only dream about. As one of the youngest self-made billionaires in the world, Kylie is part of the most well-known families in the world while making money for the very privilege.
After practically growing up on Keeping Up with The Kardashians since she was a young girl, Kylie is very comfortable in the public eye (even though she's made a few comments on TV about not wanting to be famous). She's never not dolled up for a potential photoshoot or a pesky paparazzi and she always has the latest and greatest trends.
However, since Kylie is the youngest out of the group, her momager Kris Jenner is constantly working around the clock to make sure her daughters' names are in a good standard. As they say, the Devil works hard but Kris Jenner works harder. But apparently these are 20 photos Kris couldn't keep off the Internet.
20 When She Invited Ex-BFF Jordyn Woods To Every Major Family Event
The triangle between Kylie, Jordyn, and Khloe is a sad one. Kylie practically made Jordyn Woods a family member and invited her to live with her. She went to all of the Kardashian-Jenner holiday and birthday parties and special moments. However, no one could have predicted what Jordyn was going to do to poor Khloe. And now every picture with Jordyn in it is spoiled.
19 When She Practically Hunted Tyga Down As A Teen
If you can think way back to one of Kendall's earlier birthday parties, she had a new up-and-coming rapper perform at her party. Who was that rapper? Tyga. Kylie is two years younger than Kendall and Tyga is seven years older than Kylie, so the fact that little miss Kylie was so excited for this man to perform and dated him a few years later is rather eye-raising...
18 Kris Is Always On Damage Control
Aside from playing around with makeup, Kylie Jenner also loves to play around with different hair shades. As strange a color it may look in the bowl, Kylie always looked so trendy! Except for this mid-eye-roll picture on the left... Everyone makes silly faces when people aren't looking but Kylie doesn't have that luxury.
17 Posing With Kardashian-Jenner Enemy #1
Long ago before Kylie and Tyga started dating, Tyga was engaged to Blac Chyna (who is also the mother of his son). However, after Tyga and Kylie hit it off, he blew off Blac Chyna and began dating Kylie. Even weirder, Blac Chyna went on to date Kylie's brother, Rob! Nowadays, Blac and Rob are no longer together but they do co-parent their daughter, Dream. However, Blac and the rest of the Kardashian-Jenners are not in a good place.
16 Gorgeous At First Glance (Until Eagle-Eyed Fans Notice The Photoshop)
The Kardashian-Jenners are not afraid to play around with Photoshop. And as annoying as it is that these women to feel like they need to be perfect all the time, they are constantly picked-on for simply living, so they may as well shoot their shot. However, as pretty as Kylie looks here, fans noticed that her belt loops were elongated and that some of the boxes were misshaped, which lead to them noticing Kylie's Photoshop skills.
15 Having Bad Makeup As A Makeup Mogul
It's not typically ideal for a makeup mogul to be seen with bad makeup. And even if Kylie was in the middle of getting her makeup done in the picture on the left, it's not her best look. Kris Jenner probably did her best to shut the Internet down but her efforts failed her.
14 Kylie Loves FaceTune
No matter how sly celebrities think they are, they can't fool fans with anything better to do than zoom up on their IG pictures. Kylie posted a picture a few months back of her and her baby daddy Travis Scott, but if you look closely, you can see that the car lines are a little wonky. Knowing Kylie FaceTuned this picture gave fans the ammo they needed to go after her
13 'Is That A Chicken?'
If you can remember back to this Kardashians episode, Kris comes home with a baby pig all wrapped up in a baby blanket. Granted. Kylie was upstairs without the best view but she got one look of that pig and asked her mom if it was a chicken... As you can imagine, this image has been created into a meme thousands of times.
12 Invasive Paps
It's never a good day when the paps get your bad side or catch you in a moment where the wind blows your dress up. But poor Kylie Jenner lives in the public eye where this is a very real occurrence. When you think about how young Kylie is, it's pretty sick that images like this can even be found on the Internet.
11 Having Too Much Fun Under 21
Kylie didn't turn 21 until a year ago, which means her days of her partying were mainly done under the county's legal age limit. (Is it weird that we can tell her age-range based on her lip size and hairstyle?) In the picture above, Kylie is seen leaving a club and tripping over herself. Although she has security all over her, Kris Jenner is never a fan of sloppy kids.
Ah, Kylie Jenner and Jordyn Woods before their glow-up. This photo is actually quite rare when you think about it because Kylie and Jordyn are hardly ever seen without full hair and makeup. In the photo above, Kyle still has her natural lips and Jordyn looks like an entirely different human being.
9 A Thoughtless Magazine Spread
We're not sure who the stylist or photographer of this shoot was but it has to be the most thoughtless and insensitive photoshoot a Kardashian has ever done, and that's saying something. Kylie can be seen in an old-fashioned wheelchair, making being handicapped fashionable? If they wanted a model in a wheelchair, why not hire a model who actually needs a wheelchair?
8 When Her Myspace Account Was Found In The Archives
Myspace was such a special time for those who were around for it. It was the social media network that started it all. And once Kylie became popular (and Myspace didn't), people went back to the archives and found Kylie's old Myspace photos. There were a ton of selfies, pictures in school, and yes, pictures by her mom's wine rack...
7 Her TMI Moments on Snapchat
Kylie really is the Queen of Snapchat. She has millions of followers and snaps herself doing the most exciting to mundane things. No matter what she does she gets a reaction. And in this instance, Kyle snapped herself a few times because she spilled her drink on her pants (and she apparently *always* spills her drink). However, the images she took of her and her wet pants were, of course, sultry.
6 When She Was Caught Sneaking Into A Club
If it's hard for college-aged girls to sneak into bars, why is it so easy for Kylie Jenner? She's under the legal age, which means the bar or club can be fined a hefty amount or shut down if the cat's out of the bag. Not to mention it can be quite dangerous for such a young, impressionable girl to be around people way older than her.
5 And The Aftermath Of The Club With Sister Kendall
Just as we see Kylie entering a nightclub, we see her leaving one as well. Again, she's under 21 in the photo above and who is she with? Her sister Kendall! Both girls look exhausted (among other things) and shouldn't be in this given situation when they're still in middle or high school.
4 Her Inapt Handmaid's Tale Party
Hulu's The Handmaid's Tale is a stunning drama filled with NSFW storylines. While watching the show, not many people feel the need to actually want to be a handmaid, let alone throw a Handmaid's Tale-themed birthday party! Of all the themes to choose for your party, why one that focuses on a fundamentalist regime?
3 Her Own Designs That Were Met With A Lawsuit
Kylie and Kendall have their own fashion line with designs they create themselves. Call it another form of artistic expression. However, the two sisters hit hot water after combining their own images with that of legendary rappers and rock bands who never would be associated with them in the first place. Like, why is Kylie's face with Tupac and why is Kendall with Kiss? What's the correlation here?
2 When She Hung Out With A Controversial Photographer
Terry Richardson is a legendary photographer with a dark past. He's photographed hundreds of models and TV personalities but he's also been accused of some inapt behavior. To make things even creepier, Richardson has shot Kylie a few times but none were stranger than a calendar celebrating her turning 18.
1 Doing Photoshoots That Got Major Backlash
Granted, there's not much a Kardashian-Jenner can do that wouldn't upset the public but this photoshoot really did not sit well with people. For starters, Kylie looks like an entirely different species. Many people were upset with her looking like another culture and for completely altering her entire face. Let's face facts, the woman on the left is nowhere near the real Kylie Jenner.