The Return of the Roast, with Jeff Ross

This week, Jeff Ross informed me that the blouse I was wearing made me look like a used napkin from a Chinese restaurant—“How could it be ironed and wrinkled at the same time?”—and then he complimented my jewelry. Namely, “your grandfather’s watch and the engagement ring you never got.” It was one of the best moments of my life.

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.