“So how’s your anxiety?” Kim Kardashian asked little sis Kylie Jenner in a 2016 episode of Keeping Up With the Kardashians. The pair sat in the backyard of Jenner’s $3.6 million Calabasas starter home, several cameras poised to capture their every emotion. “I don’t know, I just feel like I’ve been dealing with anxiety for so long. It’s just a thing.” “Like, you just get overwhelmed?” Kim asked. “Yeah,” Jenner confirmed. Both sisters were stuck, as usual, in the traditional Kar-Jenner monotone. But then something special happened. The 18-year-old cut, for one shining moment, right to the contradictory beating heart of her reality: “Some people are born for this life and some people aren’t, and I just know I’m not supposed to be famous. Like, I can feel it deep down inside.”
Almost ten years on, Jenner is still incandescently famous on purpose. She sidles through Paris Fashion Week like she owns it because she kinda does; she sheds grateful tears about landing the September issue of British Vogue. Kylie Cosmetics is in airports across the U.S., and every few months, the 27-year-old billionaire is shilling something new, from booze to perfume to cool-girl faux leather. Oh, and Club Chalamet, eat your heart out: There goes Jenner on another red carpet in support of her boyfriend, Timothée Chalamet’s, Oscar campaign. Through it all, she is aloof, obscure, and walled off. Jenner is a paradox, one so fascinating to me I wrote a novel loosely inspired by the existential extremes of her upbringing.
Enter Life of Kylie, the Kar-Jenner spinoff that never should have existed. Yet it lives on, streaming on Peacock, as an obscure but potent monument to an esoterically specific brand of sadness. To this day, Life of Kylie remains the deepest and most fascinating look inside Jenner’s psyche that the tight-lipped star has ever allowed.
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Kylie telling her sisters she isn’t cut out for fame in a 2016 episode of Keeping Up With the Kardashians.
Somehow, less than a year after Jenner’s declaration that she shouldn’t be famous, news broke that she would be starring in her very own spinoff series. Existential dread be damned; a second season of Rob & Chyna was dying on the vine, and like all but one of her siblings (Kendall remains the only holdout), Kylie would get her own shot to secure more followers via basic cable.
It made sense strategically, if not emotionally: This was the age of King Kylie, that raucous time in the 2010s when Jenner’s aesthetic chokehold wrought a new wave of interest in the Kar-Jenner empire. Brazenly appropriated plump lips, teal wigs, and crisply defined eyebrows were the name of the game as we exited the Obama era. Jenner herself, meanwhile, was mid-metamorphosis physically and emotionally. The teen rocketed from supporting character to leading lady with the help of a deeply questionable age-gap relationship, lip filler, quite a bit of cultural grifting, and an intimidating command of Tumblr and Vine. Theoretically, Life of Kylie could follow in the footsteps of Kourtney & Khloe Take Miami or Kourtney & Kim Take New York, offering fizzy, fun, and only occasionally crushing looks inside the lives of America’s most notable socialites. It could also — of course — provide heavy product placement for Kylie Cosmetics, the brand that would eventually make Jenner a billionaire (kind of … sometimes?).
Kylie cosplays as a regular teen going to prom in the premiere episode of Life of Kylie in 2017.
The intro to the show makes clear that producers — and Jenner herself — know she’s not exactly the most relatable girl in the world. But the first two episodes of Life of Kylie attempted to give the teenager a dose of the “normal” life that had eluded her: They sent her to prom. Jenner gleefully agreed to play charity date to actually regular teen Albert Ochoa. In one of the spinoff’s lighter moments, Jenner looked at old prom pics of assistant Victoria Villarroel for inspiration. “Victoria! ” Jenner shrieked, teasing and overjoyed, chasing the other woman around the room. “We need to show this to the world!”
But the vibe in the room shifted — rather suddenly — when stylist Jill Jacobs asked Jenner why she herself had never gone to prom.
“I was homeschooled,” Jenner said somberly. “It was really sad, actually. I had to unfollow all my friends that I went to school with. They probably all thought I hated them. But I just couldn’t see it.” Jenner was visibly pained recalling this period in her life, one not so far away at the time of filming. The show cut from Jenner’s desolation to glamour shots of their star being fitted in prom dresses. Then came the confessional, when the child star recalled being pulled out of school at age 15: “not really ’cause I wanted to, but because I missed so much school ’cause I was working.”
Kylie regretfully reflects on her homeschooling journey in the same episode.
Jenner did express excitement to attend prom with Ochoa, both for his sake (he got to go to prom with Kylie Jenner) and her own. But reality closed in fast, as she and her entourage were mobbed within minutes of arrival. Jenner didn’t get to dance; in fact, everyone’s prom came to a halt as a cacophony of voices screamed for her attention. Jenner gamely posed for selfies, but the panic in her eyes was clear. It was a mad crush of bodies, a scene that would give even the world’s biggest extrovert social anxiety.
“I for sure didn’t choose this life, but I am not gonna say that I’m totally innocent, because I’m keeping up this lifestyle,” Jenner acknowledged in a confessional shortly after the incident. “I know I’m making myself more famous by having an Instagram and posting photos … but I’m not that type of person, like, where I want all the attention. I don’t like that; it actually freaks me out, ’cause it reminds me that I’m Kylie fucking Jenner.”
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At first, Jenner didn’t choose to be Kylie Fucking Jenner. It was 2006 when the adults in her family made the fateful choice to allow cameras into the home. Jenner was 9 years old. The mogul claims she and sister Kendall — then 11 — wanted to be on the show. But how could any child comprehend the implications of a reality-TV contract? Could an adult in 2006 even anticipate the kind of fame the Kardashians would reach?
“We’ve built this amazing life for ourselves, and sometimes I feel like it can be a curse,” momager Kris Jenner said in a 2023 episode of The Kardashians, the Hulu redux of the Kar-Jenner’s flagship reality show, which reportedly includes a nine-figure deal Jenner splits with her family. “Sometimes I feel like I’ve helped build something that can also be a burden. The haters, they’re so brutal sometimes … I feel bad that I’ve brought this element to our lives.”
Whether or not you feel sorry for Jenner, there’s no denying: She didn’t choose to become a famous person, and for a long time, the realities of her family’s fame affected her deeply.
In Life of Kylie’s second episode, she attempts a “normal” walk on the beach … in the middle of the night.
In Life of Kylie’s second episode, doomed bestie Jordyn Woods drove Jenner to the beach late at night. “We’re gonna be normal,” Woods said, “even if we have to do it at midnight.” Tears filled Jenner’s eyes: “I haven’t been to the beach in I don’t even remember how long,” she said. Now, she’d been papped beachside with Tyga only a few months before, but maybe Jenner meant privately … y’know, without paparazzi, but with her own reality cameras. A good character doesn’t need to be a reliable narrator, just an entertaining and complex one. In Life of Kylie, Jenner’s yearning for a different life provided this in spades.
“I just feel like this fame thing is gonna come to an end sooner than we think,” Jenner told Woods as they walked along the sand. “I’m getting the bug again, where I just want to run away. I just don’t know who I’m doing [any of this] for.”
No smiling for the cameras here: Post-breakup Kylie pouts in bed in Life of Kylie, episode four.
Fame angst was the series’ main subject matter, along with a few tangents about how hard it was to get the flighty 19-year-old to show up and film (complaints that make up several Kar-Jenner story lines even today). Sometimes these stories overlapped — like in episode four, when rumors circulated about Jenner’s breakup with Tyga. “We stopped filming for a few days,” Villarroel said, blaming Jenner’s reaction to the press around the split. When production resumed, Woods and Caitlyn Jenner found Jenner despondent in bed. Mind you, she was despondent in bed with a full contour and thigh-high boots — but who hasn’t been there, amirite? “I’m tired. I’m sick,” Jenner said, sounding glum.
“The hardest part about having a relationship, for me, is just that it’s blasted all over the internet,” Jenner then said in a confessional. “You have to hear about other people’s opinions on who you’re with. It’s a lot … I feel like I’m in a relationship with the world sometimes.”
“What I really want is to live on a farm, and have chickens and raise animals and just have a family,” Jenner said later that same episode. It was a repeat of a sentiment she expressed to Caitlyn: “One day I just really want to move to a farm and live the farm life,” Jenner said. “Move away; no paparazzi.”
Spoiler alert: She’s got a family and a few animals, but she’s also definitely still got the paparazzi.
Therein lies the rub of the farm fantasy. If Jenner didn’t know she needed to change her life to be happy, she wouldn’t have had such a perfectly crystalized dream of that life on a farm. She already had the money, the thriving business. Kylie Cosmetics likely would have taken a hit without her aggressively aspirational Instas, but then again, she wouldn’t have to keep selling pieces of herself for the Kardashian-American Dream.
Life of Kylie remains one of the Kar-Jenner empire’s most fascinating — if stilted and self-destructive — experiments in television. It’s bad TV. It’s not fun watching Jenner be that miserable, precisely because she was a real teen girl with real feelings. It’s not entertaining to want to take her by her shoulders and shout “Get out!” in nearly every scene. But it is fascinating — because whatever the options before her were at the time, Jenner’s made her choice. She yearned for a different way of life. Then she bought another custom Bentley.
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“It’s a miracle that I still have confidence,” Kylie tells her sister last year in an episode of The Kardashians that mirrored her Life of Kylie struggles.
Life of Kylie ended after only eight episodes, teasing us in the finale that Jenner was dating someone new. Within a few months, Jenner became pregnant and disappeared from the public eye for the majority of her pregnancy.
“I knew my baby would feel every stress and every emotion so I chose to do it this way for my little life and our happiness,” Jenner wrote on Instagram when she finally announced the birth of daughter, Stormi Webster.
Disappearing was the only move that made sense if you’d paid any attention to Jenner in the year or so leading up to her pregnancy. She’d been screaming into the void in a similar tenor as musician Chappell Roan did in her 2024 videos begging fans to see her as a person. It evoked Taylor Swift sneaking out of her home in a suitcase to evade the paparazzi, and Taylor Swift carrying QuikClot army-grade bandage dressing for fear of violent stalkers, not to mention the lyrics to at least seven tracks from Taylor Swift’s The Tortured Poets Department. Life of Kylie lives on as a reminder of why Beyoncé never gives interviews and of the forces that pushed Jeanette McCurdy to reject her own child stardom.
Of course a girl so anxious and sad would want to shield her unborn child from the same relentless barrage she blamed for her own damage. Was this the beginning of the life she’d so publicly yearned for? A house away from the fray, animals to care for, a baby to love?
Well … no. Since 2017, Jenner has launched too many businesses to keep track of — ventures she claims require her to stoke the flames of fame if they are to be successful. She also joined her family in their reality-TV jump to Hulu, signing a reportedly massive deal to co-star in The Kardashians. She appears in a bigger role in this new show than she ever really did on Keeping Up. Who needs peace of mind when the paycheck’s that good?
Jenner seems to have found her own personal workaround to fame: She gives us the flash of her celebrity … but very little else. These days the star is notably more private than she was in 2017. She keeps her dating life opaque; no one ever seems to know if she’s still with Timothée Chalamet, if they’ve broken up, or if she’s pregnant with his baby until she shows up as his date to the Golden Globes. Still, Jenner remains undeniably around, basking in her fashion-girlie era (“I’ve been way more into the fashion world and Fashion Week, and it’s been so much fun,” she told British Vogue in 2024) and gleefully posting referential lewks and high-budget Halloween photo shoots to Instagram.
“There’s an image I feel constantly pressured to keep up with,” she said in the first episode of Life of Kylie. “In order to, like, stay relevant for the public, I have to be on Instagram, and I have to be on Snapchat, just keeping people entertained.”
Still, since the end of Life of Kylie, the public has lost most of its access to Jenner’s inner life. When the rare exception pops up, it’s deeply curated and usually in extraordinarily vague cover stories or on The Kardashians. In the show’s third season, Jenner spoke briefly about her family’s influence over beauty standards and how her own body image has shifted over the years. In the fifth season, she broke down crying over a photo from Paris Fashion Week in which the internet thought she looked older than her 25 years. “It’s a miracle that I still have confidence and can still look in the mirror and think that I am pretty,” Jenner said in the episode.
These days, Jenner is strategic and stingy about when she’s seen and what she reveals to the public. The instances listed above are the exception — most of her appearances on The Kardashians reveal next to nothing about her inner life. All signs point to this being exactly how she wants it.
In 2024, Jenner admitted to British Vogue that she’s been getting away with walking the High Line incognito. Apparently she’s discovered the perfect combo of baseball cap and face mask to keep her on the DL. “I haven’t had one person notice me,” she said with what writer Giles Hattersley described as delight. The story feels like a direct sequel to the scene in Life of Kylie in which Woods surprised Jenner with that midnight trip to the beach. She can be normal, even if she has to do it with a face mask and artfully angled baseball cap, worried every second that she’ll be found out.
