DREAM BIG

From a reality show childhood to a billion-dollar beauty business, motherhood to the Met Gala, the youngest member of the Kardashian-Jenner family speaks to NATE FREEMAN about the playbook on navigating fame and fortune and the public relationships she inherited from the other famous women in her family. As she goes full Hollywood—making cameos in movies, working the awards show circuit, and walking the red carpets—will she keep to the script?

NATE FREEMAN

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On an evening last November, Kylie Jenner was out late at her mother Kris Jenner's 70th birthday party, held at the Warner Estate in Beverly Hills, which is owned by Jeff Bezos. When she returned with friends to her own house, about a five-minute drive away, Kylie decided to post a reel to her Instagram captioned "sharing is not caring when you're drunk at 2am after a party."

It's a pretty straightforward bit of cinema verité. Kylie's friends were seemingly tipsy and hungry and arguing over a bag of The Good Crisp Company Original Potato Chips, Crinkle Cut.

"No! And I said before—you can only have one and I've already given you three, " Kylie said, brandishing the chip bag as a shield against her best friend, Anastasia "Stas" Karanikolaou, who was lunging toward her and the bag of chips. "Why wouldn't you shaaare, Kylie!" This video racked up nearly 65 million views.

Let me offer some comparisons. The video of Charlie Kirk's memorial posted on his Instagram got just over 28 million views. The month The Atlantic posted its firsthand account of administration officials sending classified communiqu6s, its entire website got 30 million visits. The three-hour episode of The Joe Rogan Experience featuring Donald Trump, which has been cited as the reason he recaptured the presidency, has more than 61 million views on YouTube. And all that pales in comparison to Kylie and her fellow inebriated, incredibly attractive friends arguing over a $5 bag of chips.

We're well past the point where it's shocking to be famous for being famous. That's kind of the primary mode of fame at this point. But Kylie has harnessed the power of meta-fame in the age of social media better than anyone. In addition to her dayjob as the head of a viral lip gloss empire, her side gig as a reality television superstar, being a mom to two kids under 10, and maintaining a relationship with the hottest movie star of their generation, Kylie is the preeminent attention-economy tycoon of our times. Which puts Kylie in p o le p o sitio n within what's p er hap s the world's mo st culturally omnipresent and media-savvy family of the last 20 years. The crown for most popular family member has been passed among the Kardashian-Jenner clan at various points over the years. Kim Kardashian is a generational icon with more global name recognition than almost any living human and can be almost wholly credited with creating a new reality TV paradigm. Kourtney Kardashian Barker and Khlo6 Kardashian presaged the mainstreaming of the modern wellness movement when they forswore refined sugar and hopped on alkaline water. Kendall Jenner recaptured the 1990s cultural fascination with supermodels, and has become the highest-paid one on earth. They each had their year on the throne. Now Kylie has followed in Kim's footprint to forge the biggest online fan base in the family—and lodged herself firmly into household-name, center-of-culture stardom. She has more followers on one platform than the population of the United States of America. In her canonically competitive family, it's unquestionably Kylie's turn.

"She was always, she still is, so good at social media—she's so good at connectingwith an audience, and she knows what the people that love her and follow her want," says Kendall, her older sister. But the influencer landscape is getting debased and splintered and a bit draining, even for Kylie. "It's harder to grasp people's attention because there's so much out there, they might see my perfume ad and then the next 3 0 minutes they're seeing all these other ads," she tells me in January. "Everyone kind of has a brand now."

At the ripe old age of 28, Kylie has embodied the 21 st-century life cycle better than anyone alive. She was a student of the new internet, then a savant-level creator of the content it craves, then leader of an army of followers who anticipate her every drop. She's both a product of the influencerdom and its most perfect avatar. And now she's ready to tackle something else. She's taking her mastery of new media and applying it to another platform, a more classic form of screen... the big screen. Kylie's going to Tinseltown.

What does it mean for someone who's been in the public eye since she was 10 years old to be...having a moment? For Kylie, who's been famous for beyond her entire adult life, it's walking into a movie theater and seeing herself. When we met on a sunny January day, a New Yorker's dream of Los Angeles in winter, the Hollywood premiere of The Moment— Charli xcx's bizarro Brat summer mockumentary, where Kylie makes a brief but memorable cameo—was two days away.

"The first movie premiere that I'm in—I'm thrilled. I'm really thrilled," she says. "This is the most excited I've been for the red carpet. Usually I'm not...." She trails off for a second. "I feel like there's so much pressure, but I'm so excited to be there."

It was a career move that shocked some of the people around her. Her social media panopticon is already in so many ways bigger than the 600 movie theaters that an independent him might play in. "I remember Kylie mentioning that she was interested in acting, and I wasn't sure if she was being totally serious or not," says Aidan Zamiri, the director of The Moment and a friend of Kylie'swho also works with her boyfriend, the actor Timoth6e Chalamet, on some of his viral social media spots. "Her expressing interest in being in our him...that's crazy."

Her role speaks to where Kylie is in 2 026, what her relationship to the culture has become. She's playing an over-the-top version of the incredibly famous Kylie Jenner who, while relaxing at a high-end spa in Ibiza, bumps into an over-the-top version of the hard-partying pop star Charli xcx, who is in a debilitating funk. She doesn't know if she can maintain the whole "Brat" thing and is convinced she'll eventually lose all relevancy, the thing she's fought so hard to achieve. And without a shred of self-doubt, the most relevant woman on earth issues this soul-crushing diktat to Charli: "The second you think people are getting sick of you, that'swhenyou have to go even harder."

It struck me as soon as I saw it: Oh, Kylie gets it. In fact, she came up with the entire scene herself. "I kind of presented the idea, actually, to Aidan as a joke, " Kylie says. "Iwas like, 'Well, if you want me to be in it, I would love to.' I felt like it was a comfortable avenue for me because I knew him, I know Charli, and I felt like for my first thing, this would be the perfect fit. They came back, and Charli was really excited, and they legitimately wrote me into the script, and I was like, Oh shit. Now I have to do it. "

THE CROWN FOR MOST POPULAR FAMILY MEMBER HAS REEN PASSED AMONG THE KARDASHIAN-JENNER CLAN AT VARIOUS POINTS, AND IT'S UNQUESTIONABLY KYLIE'S TURN.

There's no doubt that reportedly cohabitating with the most in-demand silver screen icon since Leonardo DiCaprio has upped Kylie's Letterboxd game. "I've actually gotten a few scripts, nothing that I feel is right yet, but 1100 percent want to do more," she tells me. "I really like comedy. I think I'm good at it." She pauses. "Maybe next time I talk to you, I'll be the lead of an action movie! "

So who's her dream director after working with Zamiri?

"I'm a fan of so many amazing directors, but I don't know, maybe I need to dream bigger or something," she says.

"Dream big," I say, repeating the slogan of a recent Oscar contender.

"In the last years of my 20s, I want to focus on just me, my businesses, my work, travelingwith my kids, enjoying my kids, and then..." she says coyly.

"I do want to have more kids...."

Back in January, Kylie had invited me over to her house, a 15,000-square-foot mansion on the most exclusive street in the best nook of Los Angeles, a storied micro-neighborhood of homes that have put up movie stars for a century.

It was always going to be a paraglide into the uncanny valley when meeting Kylie in person. There was a sort of cognitive dissonance at play—the fact that she's turned being genuine on the internet into a full-time job—that didn't fully dawn on me until I was standing in front of these gigantic castle doors, past the even more imposing 20-foot gates with a security detail, and suddenly when they opened, there she was, smiling, ready to hang.

Kylie walked me past the foyer (which had a series of matte-black fire features), the agora (filled floor-to-ceilingwith art and fashion books), and the basketball pickleball courts before we settled into the massive open-air space for entertaining. The artist James Turrell's work is installed in the poolside cabanas, and there is a palm tree in the middle of the courtyard.

I wanted to get intowhat, apart from movie magic, she sees as the next stage of the Kylie factory: how she's expanding the beauty and fashion brands that made her rich and how she's leveraging her social media kingmaker status to build a pan-cultural fiefdom. But before all that, I wanted to know more about her relationship with Chalamet.

Despite the couple'syearslong efforts to lie low, something seems to have shifted recently. In December, Chalamet hopped on a track with EsDeeKid, and nestled in his bars is a pretty clear nod to Kylie: "It'sTimothée Chalamet chillin', tryin' to stack $ 100 million / Girl got a billion / What the fuck, what a wonderful feeling." And in return, perhaps the most consistently visible she's been off-screen in years, Kylie has been working the awards circuit, accompanying her boyfriend as he goes for Oscar gold for his role in Josh Safdie's Marty Supreme. A few days prior to our interview, Chalamet won the Critics Choice Award for best actor and thanked his "partner of three years": "Thank you for our foundation. I love you. I couldn't do this without you. Thank you from the bottom of my heart," he said from the stage directly to Kylie, who seemed to melt at the recognition of what was going on before mouthing back, "I love you. "

"Is it fun to be shouted out onstage?" I ask.

It's the only time in our interview that Kylie gets flustered, but in the most charming way possible—she gets legitimately heart-fluttery, shy about how to truly answer. She wasn't expecting any direct questions about the relationship.

But hadn't he gone in front of the goddamn Critics Choice Awards and told her he loved her? Hadn't she posted his Golden Globe statuette in a carousel of after-party pics to Instagram, and as such, to the whole world? It was a far cry from the years of tabloids reporting every sighting of them together and tracking the couple's efforts to maintain a level of absolute secrecy.

"Isit>z?"

"Of course," she says, blushing.

Their relationship has the general public whipped into a frenzyhow can he be with her? How can she be with him? Maybe that's because, despite the fact that they are two of the most famous people of their generation, Chalamet's in the midst of a nonstop multiplatform charm offensive of an Oscars campaign, and suddenly it's apparent that we kind of don't know all that much about Kylie. She's spent her life in the spotlight avoiding performative IRL gestures.

Because we all collectively first met Kylie as a nine-year-old on Keeping Up With the Kardashians and forever think of her as the littlest of the principal kids, she's the product of a time warp, an optical illusion of watching someone age in real time on a TV show that's supposed to be reality. But the question has always been: What goes down on the other side of the screen?

If you type "How did Kylie..." into Google, it auto-populates a simulation of our collective imagination, a look into the id of the Kylie fan:

how did kylie jenner get famous,

how did kylie jenner make her money,

how did kylie jenner change her face,

how did kylie jenner get rich?

In search of answers, I started with the visionary behind much of the Kardashian world. "I say this about all my kids, but Kylie is one of the kindest, most generous young ladies I've ever met," says momager Kris. What makes this all the more remarkable—even coming from her mother—is the hoops she had to jump through to cultivate a cool-girl persona while growing up in an unprecedented context.

"KYLIE, ON A PERSONAL LEVEL, IS SO GROUNDED, SO CHILL, BUT WHAT SHE REPRESENTS IS A SORT OF MODERN MYTHOLOGICAL FIGURE."

—AIDAN ZAMIRI

She was raised by a family that built a multibillion-dollar media and apparel business not despite their world-historical dysfunction but on the back of it. Let me present you with a hyper-condensed history of two decades of on-camera Kardashian drama:

Kim'smarriage got annulled after 72 days. Khloé'sthenhusband, Lamar Odom, spiraled into drug abuse, was found unconscious at a Nevada brothel called Love Ranch, and suffered 12 strokes and six heart attacks while in an extended coma. Kylie's partner Tyga previously had a kid with Blac Chyna, who went on to have another baby with her half brother, Rob Kardashian. Kim threatened to fire Kourtney for "hiding" her personal life, and Kourtney slapped Kim in the face. After coming out as a transgender woman, Caitlyn Jenner revealed her new name on the cover of this magazine. Kendall's Pepsi commercial—where she leaves a fashion shoot to join a protest and gives a can of soda to a police officer—was pulled from the air after widespread condemnation. Kim got robbed at gunpoint in Paris. KhkU's partner Tristan Thompson was caught cheating on her with Jordyn Woods, who was at the time Kylie's best friend. And then there was the Kanye West of it all.

And yet Kylie has emerged as shockingly, almost disconcertingly normal. Even though she started as an unwitting participant on the cable show on E!, she was also a famous young person during the first wave of social media, the test case for a generation that embraced the power of being onscreen—"She's a Leo, so she was the entertainer of our duo," Kendall tells me. Therewas a self-imposed Truman Show going on: Keeping Up With the Kardashians didn't film at her school, so she duly documented being a teenager all by herself, turning her upbringing into an extension of the cable TV content.

"I don't think any of us knew what we were getting ourselves into inthebeginning," Kylie tellsme. "Iwas nine, I have a daughter now who's turning eight, so it's crazy to see her and how young she is. And this is when you start creating your first memories. It's almost like I just don't know anything else. I never got a taste of normalcy as an adult. Growing up in it almost was a benefit to me because I don't have anything to compare it to, really."

Eighteen years later, she still knows exactly what she's doing. It turns out Kylie has a Warholian grasp on how fame operates and a new-media savant's understanding of how images disseminate into the world. And like Warhol said, "Making money is art, and working is art, and good business is the best art." Every aspect of her business exactingly reflects her own taste, which was forged in the fire of dialogue on Instagram comments. One could argue she's not just an artist, but the first one to make a fortune off the Like economy.

To use an art-world framing, what makes Kylie's image-based practice so indelible, so addictive, is the way she inhabits that fuzzy gray area between fact and fiction. Her enormous popularity stems from the fact that Kylie-ness is theoreticallyjust as accessible as lipstick—but she's also a fictionalized version of that aesthetic, one that exaggerates reality: the bombshell, the billionaire, the starlet with the movie star boyfriend. The hundreds of millions of people who follow her are aware of this disconnect and embrace the contrived aspect of her persona in away that's more meta than classic Hollywood hero worship.

It's something that Zamiriwas grappling with while wilting Kylie's scene in The Moment. He wanted to take an experimental approach to her public image, her business, and explore how her identity has been "warped, consumed, refracted, and reflected in the public eye. "

"Kylie obviously, on a personal level, is so grounded, so chill, but what she sort of represents is like an almost modern mythological figure," Zamiri says. "That's why it was so interesting to have her in the film. It's almost like this was a Renaissance painting or something— we have Kylie as this amazing symbol of the world that we live in."

Even before Hollywood took notice, Kylie's cultural impact was felt in fashion. In 2023 she showed up to the Schiaparelli show at Paris Fashion Week wearing a dress affixed with a lion's head, designed by creative director Daniel Roseberry. "First impression was that she was vibrating on a different frequency than the rest of the room," Roseberry tells me. "I imagine her playing with her beauty like a producer in a recording studio. She's turning the bass up, the treble down, cranking the volume at this part, adding distortion in this moment. But whatever it is, it's drop-dead dialed-in gorgeous. We are watching a woman at play with herself and her own image. "

Kylie, of course, is no regular model—she's a figure who can shift global markets just by wearing a dress. Her appearance in the lion's head dress generated $2.1 million in media impact value for Schiaparelli, according to brand analysis by Launchmetrics.

"I think Kylie is one of one," Kris says. "Some people don't have the eye for being able to put things together a certain way, that artistic vision. And she's just got this level of creativity. A lot of us, just in my family, we just go to Kylie for a vision, an opinion."

Even as a teenager, there was a dialogue between her and her fans—and her fans wanted to knowwhat she was putting on her lips.

"Every other comment under my post I remember was like, 'What shade are you wearing? What lip liner are you wearing?' " she says. In order to get Kylie's full-lip look, tweens would suck on glass bottles or shot glasses, often to the point of bruising. Kylie was dramatically overlining her lips and eventually admitted to getting temporary lip fillers, but that did nothing to stop her fans from clamoring to get any tips on how to make their lips look exactly like hers. And then came Kylie's eureka moment.

"She said, T finally figured out what I want to do with the rest of my life,' " Kris recalls. " 'And I want you to figure out how to make it and manufacture it and get it done. But I know exactly what I want it to be and what I want it to look like and what I want the formula to feel like and be.' "

Kylie tried to trademark her first name in 2014—alas, the previous most famous Kylie, Kylie Minogue, blocked the effort. Undeterred, she started getting some funds together. "It was probably, like, half the money I had in my bank account. I justwent for it," she says, recalling the $250,000. "My mom was like, 'You are going to be left with lots of lip kits in your garage if this doesn't work out.' And it wasn't even a thought that it wasn't going to work out."

Kris wanted a traditional marketing strategy: newspaper ads, TV spots, the works. But Kylie had other plans. "I remember telling my mom, 'No, no, no. I'm just going to post on my Instagram.' "

Her instincts proved correct. "I remember watching how many people were waiting online for the launch. Itwasunbelievable," Kris says. "Itwas hundreds of thousands of people. You could see it in real time on our analytics system." The lip kits sold out almost instantly.

Many accused the family of creating false scarcity in order to juice the hype, but that simply wasn't the case. The Oxnard factory, which was used to cranking out this kind of stuff, just couldn't physically make enough lip kits for the number of people who wanted them. "It wasn't very exciting for me for the first year because I was so stressed out that everyone would harass me on Twitter at the time because they couldn't get a lip kit," she says. "I couldn't handle it because I really wanted to just make everyone happy."

Early on, Kris and Kylie had already begun talking about Kylie Cosmetics, as it became known, as a revolutionary company, hell-bent on steering the market solely with the force of Kylie's generational influence. They teamed up with Shopify in January 2016 to handle distribution, allowing sales to fully go global. In just 18 months, the brand said it had done $420 million in sales.

"SHE HAD TO GROW UP QUICK, BUT IT FEELS LIKE THE MOST ADULT I'VE SEEN HER, ANDIFEEL LIKE SHE'S JUST REALLY IN HER GROWN UP BAG."

—KENDALL JENNER

Based on the rabid demand and explosive growth of Kylie Cosmetics, the company drew the attention of the business press. Forbes put Kylie on its cover in August 2018 with the cover line "America's Women Billionaires"...but noted inside that she wasn't a billionaire yet. They put her on the cover anyway, because, well, she's Kylie. The following March, it happened. Forbes noted that, with a company worth $900 million and $ 100 million in profit, Kylie had become the "youngest-ever self-made billionaire" at just 21 years old—"a younger age than even Mark Zuckerberg (who was 23 when he hit that mark)." Later that year, Coty purchased a 51 percent stake in the company, a $600 million investment that allowed its purchaser to value the whole thing at $ 1.2 billion. When the magazine crunched Kylie's numbers again in 2020, taking into account the sale of her stake and the publicly traded Coty filings and stats, which appeared to show lower earnings than what the Jenners had forecast, they decided to lower the appellation. "Kylie Jenner, even after pocketing an estimated $340 million after taxes from the sale, is not a billionaire," Forbes said. Regardless of whether she's locked down that third comma or not, the lip kits she launched on her Instagram were now part of an old-school conglomerate that included some of the world's most coveted cosmetics brands. The lip-kit mania also coincided with Kylie becoming a mother, forcing her to juggle pregnancy and maternity along with the incessant branding of her, not just as a member of television's most famous family but also as the model for what a Gen Z CEO can be. "Well, I got pregnantwhen Iwas 19,1 had her when I was 20—looking back on it, people are like, 'Whoa,' " Kylie says. "They don't realize how young I was, maybe because I had already had this business, and had been in the—"

"—public eye for awhile," I say.

"In the world for so long," she says.

A few years later she had another child, a son, with her then partner, the musician Travis Scott. She didn't hide her pregnancy like the first time but was hardly transparent about the relationship's turbulence . Kylie broke up with Scott in the fall of 2 019, spent quarantine with him to co-parent Stormi, recoupled in mid-2021, and welcomed Aire in February 2022, all before breaking up for good around the holidays. Little of this would be chronicled on her social media feeds. Kylie took a page from the family playbook: distract, deny, and post something else. If all else fails, get off the 'gram altogether.

In fact, several people contacted for this story declined to comment about her co-parenting situation with Scott or her relationship with Chalamet, perhaps somewhat prudent given their intense privacy and the omerta taken with the all-powerful Kardashian family. Kendall cited the lessons from watching Kim, Khlo6, and Kourtney deal with their personal dramas growing up.

"We learned how we wanted to take control of our private lives as much as we could," Kendall tells me. But "Eve seen so much beautiful growth in her, and she's really come into herself in such an awesome way.... She had kids really young, so she had to grow up quick, but it feels like the most adult I've ever seen her, and I feel like she's just really in her grown-up bag."

When I spoke with her, Kendall also took a moment to note, wink-wink, nod-nod, that Kylie is very happy and grounded at the moment, for some unspoken reason.

Over the course of this year, I had a small but potent squad of Kylie-philes asking me the same question, hoping I could get a definitive answer into the public ledger: Are Kylie and Timmy areal couple? Yes, they are. And besides the recent surge of PDA, maybe the most endearing sign of their shared affection is...poker night.

"I grew up here, but I don't really have, like, a nightlife—I play a lot of poker, " Kylie says. After our interview, she tells me she hosts poker nights at her house with Chalamet and his gang, a mix of Hollywood types and art-world card sharks. (She actually hosted everyone at her pad the night before I visited, but there were no lingering signs of degenerate gambling on the premises.) I mention to Kylie that I had seen the most recent post on her Instagram story from the night before: a poker table with some chips on hand, a flop, some money.

"Last night wasn't a good night for me," she laughs.

Was the art gang there? "Oh my God, I played with Jonas last night. And I think I'm going to go to his tournament," she says, referencing the painter Jonas Wood's annual World Series of Ail Poker event. For years, Wood has been running a game out of his studio, eventually welcoming all the heavy hitters in the LA art scene, as well as movie stars such as DiCaprio, Ellen DeGeneres, Jack Black, as well as Kylie and Chalamet. It is certainly the only place in the world where you can see Benny Blanco and Richard Prince anteing the same hand.

"I love playing with them because they bet big and theyjuice the pot," Kylie says. "When you play a lot, to play with people who play it safe all the time sometimes isn't as fun. It's challenging because then they're betting big." Not to overextend the poker metaphor here, but it's kind of the best way to sum Kylie up: She made a career out of going all in. Regardless of whether she's a nepo baby or self-made, you can't deny that she has always bet on herself. And after spending time with Kylie, I got a sense that, despite her freewheeling charm, there isn't all that much left up to chance.

"Good luck on the poker table," Kylie tells me as I leave her house, the gate snapping open again, letting in the outside world, or at least the version of the real world that is high-status Los Angeles. The followingweekend, the final 10 players in the World Series of Ail Poker convened at a card table set up at The Living Room, a super-private Hollywood member's club—and Kylie was nowhere to be seen.

After I left the poker game, I noticed Kylie had been Instagramming from home right as the tournament was hurtling toward its big-money ending—a tease for her new Butter Cake Lip Butter. A new Kylie Cosmetics product drop was a few days away. In Kylie -world, it seems you make your own luck.

FOR ADDITIONAL FASHION CREDITS, SEE PAGE 111.