“The watercooler chatter from the first episode [of Keeping Up with the Kardashains, which debuted on E! in 2007,] was all about Kylie jumping on a stripper pole,” KarJenner matriarch Kris Jenner recalled of her youngest daughter to The Hollywood Reporter in August. “Kim [Kardashian-West] had one installed in my bedroom and our friend Robin Antin, who is the founder of The Pussycat Dolls, was just messing around, and Kylie hops up there, twirls around a couple times, and it became this thing … When I look back on that, I belly laugh.”
But growing up on camera wasn’t always a laughing matter for Kylie.
“I started filming Keeping Up with the Kardashians when I was 9-years-old. I really don’t know what it’s like to not have everyone know who I am. I don’t know what it’s like to live a normal life, where people just don’t know who you are, to get out of the car and not have everyone stare at you,” she said in August on her KUWTK spinoff Life of Kylie. “I feel like when you grow up on camera, people think that they know you because you’re on social media so much and you’re on reality TV.”
“I had to get home-schooled, not really because I wanted to but because I missed so much school because I was working,” she continued. “It’s hard to feel normal.”
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“Kylie and I did a magazine signing for Seventeen, and it was at some store at The Grove [in Los Angeles] and we had a crazy line around the corner. The store owner came up to us and said, ‘Justin Bieber was here a week ago and didn’t get this response,’ ” Kendall has said.
As Kylie entered her teens, she became increasingly involved in KUWTK and she and Kendall began to make “Jenner” as popular a last name as “Kardashian.”
In 2011 Kylie and Kendall were featured in Seventeen magazine’s Style Stars of the Year. The following year they walked the red carpet and interviewed talent at Hollywood premieres including one for The Hunger Games and guest-starred alongside Kris on an episode of America’s Next Top Model.
The sisters launched clothing, jewelry, handbag and shoe collections together but as time went on Kendall found success as a model and Kylie started on solo projects revolving around her love of cosmetics.
In 2015 Kylie, then 17, revealed Kris “cut me off financially three years ago, so I pay for everything.” At the time a source explained to PEOPLE that Kylie still lived at home with “a refrigerator full of food and all the luxuries that come with [living with] Mom but unless it was a gift, if she wanted a new Chanel bag, Kylie was the one paying for it.”
“I’m so proud of Kylie because I love her self-security at a young age,” Khloé told PEOPLE of her sister’s confidence in 2016. But Kylie made international headlines in 2015 when she revealed she’d gotten lip injections and admitted one of the reasons for the procedure was, “I felt like no one wanted to kiss me.”
The injections inspired a controversial social media challenge but proved to be the perfect media firestorm to help launch her self-titled lip kits, which debuted in November 2015 and has helped her Kylie Cosmetics brand already rake in a reported $420 million.
“I had the opportunity to make like the coolest makeup line that I’ve always dreamed of,” Kylie said on her reality show. “It’s really my only passion. I learned a lot though and just have experienced things that people my age do not even know how to handle.”
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But with major success comes media scrutiny and Kylie has found herself in the center of controversy more than once in her decade in Hollywood.
She was photographed along with her sisters Kim and Kendall texting during what was intended to be a moment of silence for Michael Brown at the 2014 Music Video Awards. The following year was accused of wearing blackface in a photo shoot she posted photos from online. (“This is a black light and neon lights people lets all calm down,” she wrote on Instagram at the time.) And a few months later she was criticized for “appropriating” black culture by wearing cornrows.
Her love life has also been the subject of much discussion among her a fans and the media – from her adorable photos with Cody Simpson when she was 14, to the rumors of dating Justin Bieber and her on-and-off relationship with Tyga (she was 17 and the rapper was 24 when they started posting photos of each other on social media) — but the reality star, who has shared so much of her life on social media, has notoriously remained quiet about her boyfriends.
“When you involve the whole world, everyone has an opinion,” she’s said. “It’s not the healthiest. That part of your life should remain sacred.”
“I feel like this fame thing is going to come to an end sooner than we think,” she said on Life of Kylie, which was hugely successful for E! but has yet to be officially renewed for a second season. “I’m getting the bug again, where I just want to run away.”
And while her sisters Kim and Kourtney blanket their social media with photos of their children, Kylie’s fans may not be treated to the same access once she welcomes her daughter, which will happen in February, according to a source.
“Once I have a kid I’m not going to be on Instagram,” Kylie told Allure in 2016. “You know, I’ll probably delete my Instagram and just … I don’t know, live life.”