Jeff Ross is a comedian, and beyond that, the Roastmaster General. He’s been organizing roasts for over 30 years, first at the legendary Friars Club in New York and then, on Comedy Central, where he convened vicious insult-fests aimed at stars including Joan Rivers, Justin Bieber, James Franco, and Charlie Sheen. He sees his barbs—like when he told Joan Rivers that “Kanye’s mom had a better plastic surgeon,” or Courtney Love, “You’re like the girl next door — if you happen to live next door to a methadone clinic”—as, ironically, a sign of respect.

“It’s a compliment if someone takes the time to write a well-crafted insult,” he told me on my podcast, Second Thought, this week. It means you’re tough enough to take it, and, Jeff added, that “you’re important, you’re made.”

Still, the Ross rules of engagement are real. He won’t roast people who aren’t in the room, and he lays off the low-hanging fruit, like about “Jewish people having big noses or being cheap,” even though at the beginning of his career, that kind of material would kill.

Lately, Ross has taken his talents to Netflix. He most recently convened a roast of Kevin Hart; it was livestreamed, glitzy, and below the belt, and clocked in at over three hours. It premiered at 13.5 million views; now, he says, it’s likely closer to 20 million.

Ross served as a producer and roaster at that event, and at the roast of Tom Brady, where everyone from Tony Hinchcliffe to Rob Gronkowski went scorched earth on the retired football player. There, Jeff told Tom Brady, “You’re an example to future generations that if you work hard, eat right, film the other team’s practices, deflate the balls, and have the NFL make new rules just for you, then you too can be the third-most famous guy in a Dunkin’ Donuts commercial.” He also got a talking-to after he poked fun at New England Patriots owner Robert Kraft for a (dismissed) charge of soliciting prostitution. “Don’t say that shit again,” Brady told Jeff. It was a moment that smacked of Will Smith’s notorious Oscars slap—but this was blessedly less violent. I asked him about it. “Sometimes in a courtroom you’ll object on behalf of a client. They know it’s bullshit, but that’s their job to object. I think Tom did that for Robert Kraft.”

I also asked Jeff why he thinks roasts are making such a comeback—and the appeal of the roast as an art form.

“The tension of the roast kind of reflects the tension of the country,” he offered. Also, “there aren’t that many platforms for unfiltered First Amendment free speech.” And besides, if laughter is the best medicine, he added, “Nobody wants their medicine watered down. They want their medicine pure.”

I would describe Jeff Ross as a pure man. Purely funny, and, ironically, purely sweet for a guy who keeps the lights on with jokes such as saying to Shaq about the World Trade Center coming down on 9/11, “I’m sorry, Shaq, I know that was your favorite building to climb.” “I got away with being mean by actually being nice,” said Jeff.

Jeff is the standard-bearer for the age-old tradition of If you got something to say, say it to my face. I cautiously asked him to do the same for me, and he delivered. Watch Jeff take his best shots, and hear more about how he came up and why he thinks roasting might be just the thing to heal our deep divisions, below:

An Afternoon in the Abundance Age

I am far from an early adopter when it comes to personal gadgets. I don’t have a washing machine, a television, or even air-conditioning in my home. But I was inspired by my conversation last week with Joanna Stern, who spent a year threading AI through her everyday life, so decided to offer myself up to the tech gods this week—or at least their angels. Cleaners arrived at my door in white collared shirts, with cameras mounted on their hats; they were there to wipe down my apartment for free. Later, a chef turned up to make me some gourmet lunch. The catch was that everyone who came to staff up my barely-a-one-bedroom that day was filming the whole time—sans sound, I was told, and with identifying information blurred—and that the footage would be sent to an AI lab that would use it to train autonomous robots or sell it to a third party. The bet is that someday robots will be able to do manual tasks, in addition to the digital ones they’re already doing, and that valuable human-generated “egocentric data,” as it’s called, will get us there faster.

Read about my afternoon peering into the age of abundance, or at the very least the perfectly cooked branzino I ate for lunch, here.

Here’s What Else I’m Thinking About

I’m a bandwagon New York Knicks fan, and I wasn’t locked into until—I’ll say it—game four, when the team came back from a 29-point deficit to defeat the San Antonio Spurs. Now I’m all, Go, New York, go! And then I find out that our star player, Jalen Brunson, married his Jewish high school sweetheart, Ali, and that he proposed to her in the auditorium of their Illinois high school? Give me a break! My second favorite character on the Knicks is, of course, the second coming of Boss Tweed, owner James Dolan. Let’s go Knicks!

If you’ve been reading The Free Press, you know that the state of American dating is in dire straits. People are suffering from an epidemic of loneliness, and trudging through a sexcession. So it’s not surprising that old-fashioned matchmakers are having something of a renaissance. Except, the problem with dating doesn’t seem to be a dearth of eligible people, but insane expectations around everything from baldness, to height, to politics, to “attachment styles.” Tablet spoke to some professional yentes about why their business is booming—and why they’re more concerned for their clients than ever.

What does it take to bring someone who is on the brink of committing terrorism—and how do you get them back into polite society? That’s the story my colleague Maya Sulkin reported on this week. In the latest episode of her Confessions series, she spoke with Mubin Shaikh, a man who had a normal upbringing in Canada, but found himself mixed up with the Taliban, and in a Canadian jihadi network. Now, he’s changed his mind completely, and has become a leading expert in de-radicalization. “Shame and guilt. Shame and guilt,” Shaikh said about how he would recruit young Muslim boys into more radical religious positions. “What a weapon those things are.”

This week, SpaceX registered for what is set to be the biggest IPO in history. The company came in at a $1.77 trillion valuation—and now, over 4,000 of its employees are set to become millionaires. But it’s not just those with equity who are benefiting. As my colleague Sean Fischer wrote this week, the company’s contribution to the rest of the country is in how it’s reviving American manufacturing—only this time in outer space. Read his piece about Varda, the company making drugs of a quality only possible beyond the earth’s gravity.

It’s stone fruit season—the best of all seasons—and you might be noticing that when you go to pick up a peach, or cherries, or other fruits, at the grocery store, they’re impossibly bright, plump, and, most of all, too sweet. Read Ellen Cushing on how the fruit-industrial complex came to be, and how it engineers nature’s candy.

Today, he joins Suzy Weiss to break down …

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We live in an age of outsider politicians who are deftly using social media to get and hold onto power—to the surprise of everyone else, including their wives. Melania Trump never thought she’d be First Lady of the United States, and yet there she is, mournfully decorating Christmas trees and picking out chargers for state dinners when she should be doing damage at a galleria. Rama Duwaji, Zohran Mamdani’s bride, was reportedly unenthusiastic about leaving Astoria for Gracie Mansion. “It’ll be fine. I’ll be down the street from the Guggenheim and the Met,” she told New York magazine.

But on the West Coast, there are so very many first ladies-in-waiting. There, any woman worth her salt is always ready for a close-up, and has a closet full of costumes to play any part. And for the second time, the former reality star Heidi Montag might just be getting the call that she’s been cast as herself.

That’s because she’s married to Spencer Pratt—who, following in the footsteps of both New York’s mayor and the president, is trying to post his way into office. This week, LA had its mayoral primary. The votes still have not been fully counted, but reports have Pratt in second place, with about 29 percent of the vote—which would mean he’s headed for a runoff against incumbent Karen Bass come fall. If he wins, Montag will become the First Lady of the city. But really, isn’t she that already?

Montag and Pratt—though viewers of The Hills will always remember them as “Speidi”—met on a fateful night in 2006 at a club called Privilege in West Hollywood. Their dramatic relationship—Pratt was the show’s villain, Montag the small-town transplant who promptly got implants—was the load-bearing wall of the reality series, which followed a clique of twentysomethings as they got their footing as adults in LA. “I want to be the fun party-PR-girl-in-LA type of thing,” Montag announced on her first appearance on the show, to a prune-lipped college administrator. Later, she’d call her friend Lauren Conrad, who was working a party, to deliver LA’s unofficial motto: “We’re outside. Can you get us in?”

The Hills ended in 2010, Privilege shuttered years before that, and yet against all odds, Speidi stood strong. They’ve been married for 17 years and have two sons named Gunner and Ryker, because of course. Though Montag did not go quietly into the California mom life. Like any good LA reality starlet, she parlayed her celebrity into other reality shows about being a celebrity, like I’m a Celebrity . . .Get Me Out of Here! and Celebrity Big Brother. She started putting out pop music, too. Her newest album, Heidiwood, follows the 2010 release of Superficial, which includes the head-scratching lyric “I wear diamonds for breakfast.” Her Instagram is shellacked with pictures of herself in full glam, edited to poreless perfection, in a bikini walking a German shepherd with palm trees in the background—Caption: “🚨🚨Neighborhood watch🚨 🚨”—and doing an ad for McDonald’s in a gold lamé tube top and matching Daisy Dukes. In other words, she’s already representing the essence of LA.

Besides, she has decades of experience standing by her man. Even Hillary Clinton can’t say she was loyal when her husband spread a rumor that her best friend had a sex tape—which Pratt did, about Lauren Conrad. The affection appears to be mutual: Pratt is often seen campaigning in T-shirts with his wife’s face plastered across it, and told Fox News last week, “Thankfully, I married an angel who is very connected with Jesus and has brought me to the light.”

On Tuesday, Speidi arrived at a Mexican restaurant for an election watch party; she wore a slutty rendition of a Jackie O skirt suit—bright white, with satin 5-inch pumps and a micro miniskirt and full glam. Caption? “Ex Machina,” the title of her latest bubblegum pop single. Like it or not, she was born for this.

Joanna Explains It All

Joanna Stern really wanted her laundry robot to work. “I’m not very good at folding the laundry,” said the woman who is the most readable and funny consumer tech columnist around, if not a domestic goddess. “My wife complains constantly that I’m putting glasses into the dishwasher wrong,” she told me, on the latest episode of Second Thought.

We’re constantly told something big is coming when it comes to artificial intelligence injecting itself not only into our screens, but our lives in the physical world. But: When exactly? And how? Will it be that we each have home robots like Rosey on The Jetsons? A daily pill tailored to each of us to stave off diseases that a superintelligent doctor-bot screened us for? Or should we simply just expect a gusher of AI ads and slop to glut our feeds?

That’s where Joanna comes in. For a year, she invited AI into every corner of her life. She listened to AI-generated music and took self-driving cars. Alas, for all the big talk of menial labor, Joanna reports that the laundry robot was a bust. “It can only fold T-shirts right now,” she said. “And if you’re only wearing T-shirts, you have a pretty big problem.”

But though she gave that bot a failing grade, she told me she’d be all in on AI-assisted medicine. In other words: AI will revolutionize some aspects of our life, and especially the industries that rely heavily on technology and machinery—like healthcare, and car manufacturing and driving—but not all of them. Poetry, film, and music? Better to leave those to the flesh and blood pros. You can read all about Joanna’s great big experiment here, or listen to her on Second Thought. Or watch our conversation—including Dan Ahdoot’s stylings on the culture news of the week—below.

Here’s What Else I’m Thinking About:

The new thriller Backrooms released last weekend, earning $81.5 million domestically—eight times what it cost to make. The twist? The movie was made by a 20-year-old director, who adapted it from his viral YouTube series. Read Spencer Klavan’s piece in The Free Press about why internet kids are taking over the movies—and how they just might save Hollywood from itself.

Speaking of Hollywood: This week marked the season finale of Euphoria and, likely, the end of the series. Across three seasons, director Sam Levinson chronicled the messy, drug-addled, and often tragic lives of the teens of East Highland. Adam Lehrer profiled the man behind the show, and went deep into the psyche and politics of the “god of Euphoria.”

This week, Hoan Ton-That of Clearview AI argued that actually, AI won’t be taking all the jobs: He writes that he’s addicted to Claude Code, having the time of his life—and that this tech will both empower and employ software engineers like never before, to build more and build bigger. Read his piece for a weekend white pill before you dive back into AI Armageddon talk on Monday.

They say that New Yorkers never get along—that it may well be the rudest city in the world. Except, that is, when the Knicks manage to get a small orange ball to go through a hoop more times than their opponent. On Wednesday night, the Knicks defeated the San Antonio Spurs in Game 1 of the NBA Finals and all was right on the isle of Manhattan. Now, Mayor Mamdani is signing executive orders to extend kids’ bedtimes, and President Donald Trump is planning to come back to New York, where both leaders will cheer on their hometown team. If the Knicks win their next two, expect a new Middle East peace deal by Game 4, inked over a hot dog and $30 beer.

That experiment became her new book, I Am Not a Robot. …

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And how they will make beautiful meals with ingredients sourced, of course, from the Park Slope Food Co-op.

The Co-op is one of the oldest cooperatively run grocery stores in the country. It is both an institution and an idea, that in exchange for volunteering shifts reracking carts or weighing out wedges of cheese, you too can have access to cheap, choice produce and single-source artisanal chocolate bars. The building is big and charming. About 17,000 people are members, and there’s always a chance you could run into a Brooklyn celeb—Ezra Klein!—or even a real one, like Maggie Gyllenhaal, among the dry goods.

Who wouldn’t want to be a part of it? Well, me.

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In 2007, when Scooter Braun stumbled upon a video of a 12-year-old Justin Bieber singing a cover of Ne-Yo’s “So Sick” on the streets of Ontario, he knew immediately what to do: make the teenager a global superstar. “Sometimes you get a download,” Braun told me. “A blueprint just gets sent into your head, and it’s so clear what you should be doing, and it doesn’t matter what anyone in the world tells you.”

Braun, who I recently interviewed in Los Angeles for my podcast Second Thought, told me he saw explosive talent in the young Bieber—“He was charismatic, he was brave”—and envisioned him as the 21st century’s answer to a young Michael Jackson; a kid, soulfully singing love songs for the masses. He was right. In 2008, after flying the tween Bieber and his mother to Atlanta—it was their first-ever plane ride—he signed Bieber as a client. Over the next 15 years, Bieber, with Braun behind him, would sell millions of tickets to world tours, and become the youngest-ever solo artist to have eight No. 1 Billboard 200 albums, breaking Elvis Presley’s record.

It wasn’t only Justin Bieber. Braun went on to engineer the meteoric rises of Ariana Grande, J Balvin, David Guetta, Demi Lovato, and even, for a spell, Kanye West. “If I like something, why shouldn’t millions of other people like it?” Braun told me about his populist and very “ordinary” sensibilities. On his way up “Mount Pop Music,” Braun made early bets on tech companies too—Spotify, Uber, and Dropbox among them. In other words, Braun was getting rich, his clients were selling out stadiums, and he seemed to have a Midas touch when it came to cultural resonance.

Then it all came crashing down.

One of the things that Braun understood earlier than most was the power of social media. These networks were not just for discovering acts but for cultivating and mobilizing fan bases that would stream their music, buy their merch, and sell out their concerts. “We involved them so intimately in the building that they are just as responsible for the success of these artists as I was,” said Braun, who, in part, architected the transition from old-fashioned fan clubs to hyper-online fandoms, as his acts became hugely popular on- and offline.

But in 2019, one fandom, the Swifties, who idolize the country-singer-turned-pop-phenomenon Taylor Swift, came to consider Braun their archnemesis. Turned out, hyper-intimate fan relationships cut both ways.

Here’s what happened: Swift signed with Big Machine Records, based in Nashville, when she was 15. For years, she asked to buy the rights to her masters—the original studio recordings of her, which are typically owned by record labels, and from which they get a profit when songs are streamed—but she and the label couldn’t come to an agreement. “For years I asked, pleaded for a chance to own my work,” she wrote in a Tumblr post in 2019.

Then, after a deal saw her catalog come under Braun’s ownership, she went nuclear.

“I was denied the chance to purchase my music outright, my entire catalog was sold to Scooter Braun’s Ithaca Holdings,” Swift thundered while accepting Billboard’s Woman of the Decade Award in 2019. “This just happened to me without my approval, consultation, or consent.” She went on: “The definition of the toxic male privilege in our industry is people saying, ‘But he’s always been nice to me,’ when I’m raising valid concerns about artists and their rights to own their music.” Swift vowed to rerecord her own songs as an act of defiance; meanwhile, her fans descended upon Braun on her behalf. He was the subject of death threats and endless online ire. Leave it to Swift, a master in storytelling, to take a complicated legal dispute and thread it into a story about betrayal and exploitation—with Braun at the center.

WATCH MY FULL INTERVIEW WITH SCOOTER BRAUN BELOW, OR LISTEN TO IT HERE:

It’s a story reminiscent of The Little Mermaid: A young woman sells her voice for access to a world she idealizes but doesn’t totally understand—except in this version, she fights back, unwilling to let the private equity–funded powers profit from the music she put her heart into. The saga had an air of truthiness, even if it seemed a little pat.

Except: It seems that all the contracts that Swift signed were standard for the music industry, and that the label offered her the opportunity to buy her masters—and later warned her that a deal was forthcoming. What’s more, Swift’s dad was an investor in Big Machine Records, and netted around $15 million from the sale. Braun also offered Swift the chance to buy back her masters after he acquired the label, which he off-loaded for a profit in 2020, but she refused because it required her to sign an NDA, and because Braun would continue to profit off of them.

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We spoke a lot about the apps that allow you to modify your body to make it look better on the internet, as well as the endless stream of products we’re sold to make ourselves firmer, smoother, younger, and glowier. But Freya thinks it’s not just about physical upgrades—it’s our personalities too. We’re all “being dragged by that algorithm toward an eventual end product where we all become much more similar,” she said. In other words, the future is ruled by women who all, on some level, want to look like the Kardashians, who talk like the same few influencers, and who are trying to shop or medicate their way out of insecurity.

“Whatever vulnerability she has,” Freya told me about women like this, “there is a rabbit hole she can go down.”

Freya and I spoke about eating disorders, the benefit of stigmas, women’s fear of aging, men’s anxiety around their looks—and how various corners of the internet, from OnlyFans to podcasts about how men suck, have warped sex and intimacy. Somehow, she insisted that doing the research for her book didn’t make her depressed—quite the opposite. Listen below to find out why Freya, despite believing that Big Tech has hurt Gen Z women more so than the patriarchy, is hopeful:

Eat Thy Neighbor’s Sourdough

Gabby Golden believes that God gave her the bakery, or at least the idea for it, so that she might bring in some extra income while still being able to stay home with her kids.

If so, she’s not the only one. There’s a quiet revolution sweeping America’s kitchens. Cottage foods—which is food, usually baked goods, prepared in private homes but sold to the public—have taken off. “It’s like everyone is posting ‘Hey, welcome to my home bakery,’ ” Golden told me.

Of course, producing and selling things like bread or jams from someone’s house has been around for thousands of years. But this latest cottage foods craze is animated by distinctly modern trends: side hustling to stave off inflation; skepticism of health guidelines handed down from the government; a worship of unprocessed, small-batch foods; and the on-camera appeal of removing steaming scones from the oven while toddlers and pets pad around nearby.

But lately the idyllic notion of selling chocolate chip cookies from your porch has been crashing into the reality of public health inspectors, commercial bakery owners, and legal liability. “We’re talking about food in people’s mouths,” Rachel Smith, a bakery owner in Wisconsin, told me. She told me she thinks it’s unfair for women like Golden to sell their fare with no oversight, while bakers with storefronts like her are subject to inspections, fees, and permits. Not to mention: In many states, cottage bakers don’t have to do any food-safety training. “If it’s in your kitchen, you should know how to handle it so that the end consumer is safe,” Smith added.

I spoke to cottage food producers, farmers, a public health official, and commercial bakers for my story about this trend. I learned that states have different regulations when it comes to cottage foods; there are differences in how each defines nonhazardous, for example, while various states have special carve outs for pickled foods, or tamales, or fudge. Many states have updated their books, or started doing so, to either loosen or tighten the rules around not just cottage foods but also raw milk and prepared meals. And that’s not to mention the cottage industry that’s sprung up around cottage foods: apps to keep tracks of sales and inventory, microbakery coaches, and conferences to learn about how to handle cheese safely.

On the surface, it might seem like a story about some moms selling bags of snickerdoodles to help bring in some extra cash—and in part, it is—but it gets at some of the most controversial topics in America right now. Like, who benefits from the gig economy, and who loses out? And who gets to decide what you do in your own home? This is a tale about the benefits and drawbacks, and the risk we take on, when we trade safety for more freedom.

Read my piece on cottage foods:

Here’s What Else I’m Thinking About

If you know anything about the Amish, perhaps it’s that they live life the old-fashioned way: They avoid electricity, churn their own butter, and drive horse-drawn carriages. But their new obsession is something all too new: They’ve fallen in love with AI. New York magazine went deep into the communities where TV is banned, but ChatGPT is as common as straw hats.

For a brief moment in the 2010s, Tiger Moms ruled the world. After decades of gentle parenting, moms who obsessed over their kids’ chess classes, charity work, and early SAT prep were all the rage. Now, it seems the pendulum has swung in the opposite direction: “Beta moms” are in, and they’re shrugging their way through parenthood. The Wall Street Journal heard from one mom about her 13-year-old that “she usually won’t know precisely where in Los Angeles he is.”

Last week, Canadian rapper Drake dropped not one but three new albums. The new songs are filled with pettiness, and retribution—some have speculated that even the release itself is an attempt to get out of his record deal—but, more importantly, some of them are the fun, dancy kind you will be hearing nonstop. As my Gen Z colleague put it this week: You know it’s gonna be a good summer when it starts with a Drake album. Luckily for us, we have three.

Our favorite polymath Andrew Ross Sorkin sat down with Jeff Bezos for an interview at the Florida Rocket Park factory of Blue Origin, Bezos’s space company. The conversation is full of juicy takeaways about everything from data centers in space to the future of tax policy. Jeff’s views on the AI economy are beyond optimistic: “You’ve been digging out a basement for your house with a shovel. And somebody’s about to hand you a bulldozer. You should be so happy!” Here’s hoping!

The Free Press earns a commission from any purchases made through all book links in this article.

India’s new book, Girls®: Generation Z and the Commodification of Everything, examines how algorithm-driven platforms push young users toward extremes in beauty, body im…

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On Tuesday, I wrote a piece about how, in the season of the show that’s currently airing, Sweeney’s character, Cassie, plays an aspiring OnlyFans star who is willing to do anything, pretty much, for money and attention. That includes donning a ridiculous baby costume (though more often she’s donning nothing at all), and fulfilling the requests of her thousands of male followers: for her to humiliate them, eat hot dogs in front of a camera for them, or simply whisper their name.

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Loeb opens up about creating imaginary friends whose net worths he obsessively tracked as a child, which developed into a gambling addiction that has checkered his adult life. He recounts losing fortunes shorting Tesla and spiraling through blackjack systems in Bahamian casinos—all while becoming a renowned Hollywood writer.

Suzy and Allan unpack the future of storytelling in the age of AI, why Hollywood may not be dying nearly as fast as everyone claims, Tom Holland’s attachment style, and why baseball is “the crystal meth of gambling.”

Then, comedian Dan Ahdoot joins the panel for a rundown of the week’s biggest culture stories—from the hantavirus panic to Billie Eilish’s new James Cameron–directed documentary, to the roast of Kevin Hart (the women took the night!).

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Ben Kawaller, whose name you might recognize from his Free Press series Ben Meets America and the Swing State Debates, is always game to go out and try something new—and high-end. Extremely painful dermatological treatment was no exception. “It was the worst pain I’ve ever had in my life,” Ben told me, on the latest episode of the Second Thought podcast. He was describing his encounter with a dramatic and fishy—yes, it involves salmon sperm—procedure that apparently involved 150 needles, and is illegal in America. “It felt like my skin was being slowly peeled off,” he added.

So, was it worth it? Ben shrugged: “I never feel worth it.” But I gotta say: He looks great.

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On this week’s episode of Second Thought, Suzy Weiss, Dan Ahdoot, and Ben unpack the bizarre rise of the male beauty economy. Ben recounts his surreal trip to Seoul, where he underwent a series of cutting-edge cosmetic procedures—including “Crowtox,” laser treatments, and the inf…

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This week, on my pod (subscribe here), I spoke to one of the producers of that show, Sophia Rivka Rossi. “He makes whatever he wants happen,” Rossi, who is undecided on the mayoral race for now, told me. “Every day someone else says to me, ‘I think I’m gonna vote for Spencer.’ ”

On The Hills, which debuted in 2006, Pratt did things like start a rumor that the star of the show, Lauren Conrad, had made a sex tape, which he later denied. “He knew what would be good TV,” Rossi told me. He later said he cultivated his troublemaking persona to boost ratings. But if you watch his campaign ads, you can tell: He still knows how to make TV. In a piece for The Free Press, Liel Leibovitz called his latest viral campaign ad “resonant and raw,” since, “As he’s done for 20 years now, he grabbed hold of the camera, turned it around, and told viewers an inconvenient truth.”

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Today, she pulls back the curtain.

On this week’s episode of Second Thought, Sophia joins Suzy Weiss to unpack the machine behind reality TV, the secret sauce behind Ryan Murphy’s dominance, and what happens when you finally stop ou…

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The higher that Dunham scaled Fame Mountain, the more unexplainably sick she became. She was dissociating while running lines with Adam Driver for her very own prestige television series, laid across the “cool marble floor in a sleek corporate bathroom” as Oprah Winfrey waited outside to say hello, and battled a migraine the first time that she had sex with her rock star boyfriend. She became addicted to the drug she took for anxiety, Klonopin. Dunham was getting it all and yet, simultaneously, falling apart.

The book is dedicated to all those wunderkinds who never tunneled out of that same addiction, chaos, and pressure to the other side: Whitney Houston, Amy Winehouse, Heath Ledger, “and anyone else who was too Famesick to be cured.”

But none of those guys spent their 20s performing nude on television and then reading headlines immediately after, on tiny screens, analyzing the distribution of fat on their bodies. While Dunham’s earlier output defined the hyper-confessional style that ruled the 2010s, Famesick—which, full disclosure, I’m only about halfway through but loving—might define another one, and that’s when people who became famous under the microscope of the internet look back, aghast, at what happened to them, what people said about them, and what they’ve become.

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As host of one of the internet’s most popular pop culture podcasts—The Toast, which she hosts with her sister Jackie—Claudia talks…

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Since running away from home at 15, and then starting a channel where he started posting about New York’s bike lanes and layovers, Casey has amassed millions of followers and billions of views. But I wanted to talk to him not because he’s popular but because he saw what was coming. Casey, who’s 45 now, knew that YouTube would upend media. He saw that self-appointed celebrities—the people we now call “influencers”—would dominate our screens. In our interview, he argues that the one-two punch of iMovie, which is the editing software that came with Apple iMac DV computers starting in 1999, and then YouTube, which launched six years later, would change everything about who gets to make movies and how we watch them.

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On this episode of Second Thought, I ask Neistat about riding the wave of the YouTube tsunami, his love of old technology, and how his care…

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