At ten o’clock on a recent Saturday night, the rapper Flo Rida was in his dressing room with a towel over his head, in a mode of quiet preparation. Along one wall, a handsome buffet—lobster, sushi, Dom Pérignon—sat untouched. Flo Rida, whose stage name honors his home state but is pronounced like “flow rider,” is fastidious about his physique. He is six feet three, two hundred and twenty pounds, and often travels with a trainer, though on this occasion the trip was brief enough that he would do without. That afternoon, a private jet had carried him, along with eight of his backup performers and assistants, from South Florida to Chicago. By the following night, he would be back at his mansion in Miami.

Flo Rida, who is forty-three, attained celebrity in 2008 with his song “Low,” an admiring ode to a Rubenesque beauty on the dance floor. “Low” went platinum ten times over and was No. 1 on the Billboard charts for ten weeks—a longer run than any other song that year, including Beyoncé’s “Single Ladies.” In 2009, Flo landed another No. 1 hit, “Right Round,” which broke a world record, jointly held by Eminem, 50 Cent, and Dr. Dre, for the most downloads in an opening week. Flo never matched the stardom of those peers, but he has recorded another nine Top Ten hits, sold at least a hundred million records, and secured for himself a lucrative glide from ubiquity. His endorsement deals are of sufficient scale that, in a recent breach-of-contract dispute with one of his brand partners, Celsius energy drinks, a jury awarded him eighty-three million dollars.

A man with this kind of nest egg might never need to leave home again. But, on this evening, Flo had journeyed north on business: he was playing a bar mitzvah, for a thirteen-year-old boy and three dozen of his friends, in the well-to-do Chicago suburb of Lincolnshire. The bar-mitzvah boy, in keeping with the customs of his forebears, had chanted his way into adulthood; then, following a more recent tradition, the celebrants had relocated to a warehouse-size event venue that is highly regarded on Chicago’s mitzvah circuit. A production company had installed the décor, including roller coasters stencilled across the dance floor and a banquet table made to resemble a red Ferrari. The whole affair was invisible to the outside world, except for the word “Andrew” projected by brilliant red floodlights onto an exterior wall.

The entertainment had been arranged by Andrew’s father, an executive at a financial-services company. At first, he had doubted that Flo Rida, his son’s favorite artist, would agree to come, but an agent informed him that most big-name musicians are available these days, under the right conditions. Flo Rida’s fee for private gigs in the United States runs between a hundred and fifty thousand and three hundred thousand dollars, depending on location, scale, and other particulars. Reginald Mathis, his lawyer, told me, “Internationally, it could run you up to a million.” For the Lincolnshire bar mitzvah, the contract stipulated private-jet travel, suitable accommodations, and a fee “in the six figures,” Mathis said; Flo Rida would perform for thirty minutes. When I saw Andrew’s father at the event, he was thrilled with the outcome but declined to have his name in this story. “I work on Wall Street,” he told me. “I don’t want to end up on Page Six.”

As showtime approached, Flo changed from his travel T-shirt and jeans into performance attire: a much nicer T-shirt (vintage Kiss concert merch), a sleeveless black biker jacket, and cat-eye shades speckled with rhinestones. While the opening act finished up, I stepped out of the dressing room to assess the crowd. From a balcony overlooking the dance floor, surrounded by a hefty array of professional-grade lights and speakers, I watched a desultory turn of the hora, backed by a recorded Hava Nagila. The children seemed preoccupied. Then a platoon of production staff started handing out flashing L.E.D. sticks, and the kids rushed toward the stage in anticipation.

I was joined on the balcony by one of Flo’s bandmates, a younger rapper known as Int’l Nephew, who wore a red sweatband and a black puffy vest over a tank top. We peered across the railing toward the back of the room, where a few dozen parents were sipping cocktails. In the realm of private gigs, those secondary guests are a high-priority demographic—future clients who don’t yet know it. Int’l Nephew saw the makings of a worthwhile trip. “They’re all big-money people,” he said. “And they’re, like, ‘Oh, we want you, Flo.’ ”

By the time Flo Rida bounded onstage, his hands to the heavens, the kids were bouncing to the opening strains of “Good Feeling,” one of his club hits, featuring the sampled voice of Etta James. The edge of the stage was lined by teen-age boys in untucked shirts and jeans, alongside girls in spaghetti-strap dresses and chunky sneakers. Flo was flanked by dancers in black leather bikini tops and mesh leggings. Out of the audience’s view, he kept a set list inscribed with the names of his hosts, as an aide-mémoire. “We love you, Andrew!” he shouted, and barrelled into “Right Round,” a rowdy track about visiting a strip club and showering a pole dancer with hundred-dollar bills. When he pulled Andrew onstage, the bar-mitzvah boy didn’t miss a beat, dancing along to Flo’s verse: “From the top of the pole I watch her go down / She got me throwing my money around.”

A private, as it’s known in the music business, is any performance off limits to the public; the term applies to a vast spectrum of gigs, from suburban Sweet Sixteens and Upper East Side charity galas to command performances in the Persian Gulf. For years, the world of privates was dominated by aging crooners, a category known delicately as “nostalgia performers.” Jacqueline Sabec, an entertainment lawyer in San Francisco, who has negotiated many private-gig contracts, told me, “Artists used to say no to these all the time, because they just weren’t cool.”

But misgivings have receded dramatically. In January, Beyoncé did her first show in more than four years—not in a stadium of screaming fans but at a new hotel in Dubai, earning a reported twenty-four million dollars for an hour-long set. More than a few Beyoncé fans winced; after dedicating a recent album to pioneers of queer culture, she was plumping for a hotel owned by the government of Dubai, which criminalizes homosexuality. (As a popular tweet put it, “I get it, everyone wants their coin, but when you’re THAT rich, is it THAT worth it?”) Artists, by and large, did not join the critics. Charles Ruggiero, a drummer in Los Angeles who is active in jazz and rock, told me, “The way musicians look at it, generally speaking, is: It’s a fucking gig. And a gig is a gig is a gig.”

If you have a few million dollars to spare, you can hire Drake for your bar mitzvah or the Rolling Stones for your birthday party. Robert Norman, who heads the private-events department at the talent agency C.A.A., recalls that when he joined the firm, a quarter century ago, “we were booking one or two hundred private dates a year, for middle-of-the-road artists that you’d typically suspect would play these kinds of events—conventions and things like that.” Since then, privates have ballooned in frequency, price, and genre. “Last year, we booked almost six hundred dates, and we’ve got a team of people here who are dedicated just to private events,” Norman said. An agent at another big firm told me, “A lot of people will say, ‘Hey, can you send me your private/corporate roster?’ And I’m, like, ‘Just look at our whole roster, because everybody’s pretty much willing to consider an offer.’ ”

The willingness extends to icons who might seem beyond mortal reach, including three Englishmen honored by Her Late Majesty: Sir Paul McCartney, Sir Elton John, and Sir Rod Stewart. “We just did Rod Stewart for $1.25 million here in Las Vegas,” Glenn Richardson, an event producer, told me. It was a corporate gig for Kia, the car company. “He’ll do those now, because Rod’s not doing as many things as in his heyday,” Richardson added. A random selection of other acts who do privates (Sting, Andrea Bocelli, Jon Bon Jovi, John Mayer, Diana Ross, Maroon 5, Black Eyed Peas, OneRepublic, Katy Perry, Eric Clapton) far exceeds the list of those who are known for saying no (Bruce Springsteen, Taylor Swift, and, for reasons that nobody can quite clarify, AC/DC).

Occasionally, the music press notes a new extreme of the private market, like hits on the charts. Billboard reported that the Eagles received six million dollars from an unnamed client in New York for a single performance of “Hotel California,” and Rolling Stone reported that Springsteen declined a quarter of a million to ride motorcycles with a fan. But privates typically are enveloped in secrecy, with both artists and clients demanding nondisclosure agreements and prohibitions on photos and social-media posts. Sabec told me, “They don’t want anybody to know how much they paid the artist, for example, or the details of the party. And the musician might not necessarily want it to be discussed, either.” (After the news of Beyoncé’s fee leaked, Adam Harrison, a veteran manager, told me, “That is my nightmare.” Then he reconsidered the effect on Beyoncé’s operation: “It probably raises their rates.”)

Until recently, the stigma extended beyond style. A prominent music executive said, “There was a phase where artists would take a private show—a cancer benefit—and somebody would find out that they’re getting paid to perform, and then they look like complete cocks in the media, because they took money and some child was dying of cancer. There was risk in the money.”

The risk could be especially high overseas. Before the Libyan dictator Muammar Qaddafi was toppled, in 2011, members of his family organized events enlivened by 50 Cent, Mariah Carey, Usher, and Nelly Furtado. During the Arab Spring, when Qaddafi unleashed his forces on protesters, Carey expressed regret, and the rest of the performers announced plans to donate their windfall to charity. That kerfuffle did not deter others, however. In 2013, Jennifer Lopez was hired by the China National Petroleum Corporation to do an event for executives in Turkmenistan, which culminated in her singing “Happy Birthday, Mr. President” to Gurbanguly Berdimuhamedow—one of the world’s most repressive despots. After a video of the serenade emerged, Lopez’s spokesman assured fans, “Had there been knowledge of human-rights issues of any kind, Jennifer would not have attended.” But the Human Rights Foundation, an advocacy group based in New York, subsequently estimated that Lopez had garnered at least ten million dollars in fees performing for “crooks and dictators from Eastern Europe and Russia.” The foundation’s president, Thor Halvorssen, asked, “What is the next stop on her tour, Syria?”

The opprobrium dissipated before long. In 2015, when critics urged Nicki Minaj to forsake a reported fee of two million dollars for a concert sponsored by a company linked to Angola’s dictator, she dismissed them with a tweet: “every tongue that rises up against me in judgement shall be condemned.” The music executive told me that there is even a sense of commercial competition among stars, who now measure themselves as entrepreneurs. “If you’re Kevin Durant, and you don’t have five businesses, you’re a schmuck,” he said. “ ‘I made twenty-five million dollars playing ten birthday parties.’ That used to be seen as ‘You fucking piece-of-shit sellout.’ Now it’s ‘How do I get me some of those?’ ”

At bottom, the boom in private gigs reflects two contrasting trends. One has to do with the music industry. For more than a century after sound was first captured on wax cylinders, in the eighteen-eighties, the money came mostly from selling recordings. But that business peaked in 1999, and, as CDs vanished, revenue sank by more than fifty per cent. It has recovered on digital subscriptions, but the new giants—Spotify, Apple, YouTube—pay artists only a fraction of what physical sales once delivered.

The other trend is the birth of a new aristocracy, which since 2000 has tripled the number of American billionaires and produced legions of the merely very rich. As musicians have faced an increasingly uncertain market, another slice of humanity has prospered: the limited partners and angel investors and ciphers of senior management who used to splurge on front-row seats at an arena show. Ruggiero, the drummer, told me, “People didn’t use to do this, because they couldn’t afford to have, like, the Foo Fighters come to their back yard. But now they can. They’re, like, ‘I can blow a hundred and fifty grand on a Thursday.’ ”

Ask a dozen event producers if they’d rather work with a hip young phenom or a pro in the second act of a career, and you’ll hear a consistent reply. “The one you have to watch out for is the up-and-comer,” Colin Cowie, an event planner in New York and Miami, told me. He aped a litany of demands: “I need this car! I need my d.j. rig to be in the middle of the room! And I need this type of room!” Willie Nelson, by contrast, is still booking privates at the age of ninety, playing a guitar so ancient that he has strummed a hole in its face.

Flo, whose real name is Tramar Dillard, is the workmanlike kind of star. The youngest of eight children, he was raised in Miami’s Carol City housing projects—a shy kid who became a performer only in the seventh grade, after a teacher punished an infraction by forcing him to join the speech-and-debate team. Two years later, he became a member of the Groundhoggz, a rap group that opened for local artists, and soon he was a hype man for 2 Live Crew, the X-rated pioneers of the Miami sound known as booty bass. Flo did brief stints in college in Nevada and Florida, but he spent most of his time cold-calling studios, seeking someone who would record him. At one point, he rode a Greyhound bus to Los Angeles but was rejected by the major rap labels, and ended up sleeping in motels and, occasionally, on the street. In 2006, he signed with Poe Boy Entertainment, a hip-hop label in Miami. Within two years, he was on the charts, building a reputation as a purveyor of technically adept, if unchallenging, ladies’-man tracks about partying, spending, and vamping. An article in Vice once summed up his success with the headline “Flo Rida Is Boring. Flo Rida Is Perfect.”

Mathis, his attorney, is a former prosecutor and corporate lawyer who joined Flo’s operation in 2011, agreeing to help oversee its growing presence on the private-gig circuit. In that milieu, blandness can be a superpower. Flo can get along with “any- and everybody, from the emirs in Dubai to the thugs in Carol City,” Mathis said. First, though, there were some adjustments to make. During one foray into corporate work, Flo arrived late for a Samsung event, and the C.E.O. had already left for a flight to South Korea. “It’s been ten years to repair that situation,” Mathis said. “For Asians, in particular, punctuality is important.”

Mathis took it upon himself to help the performers make sense of the worlds they were suddenly encountering. In 2012, Flo was hired to play at a benefit for veterans alongside the Democratic National Convention. Mathis, a savvy political observer, briefed the team: “I’m, like, ‘Yo, Bill Clinton is speaking tonight, and you’re the entertainment for when he finishes.’ ” Members of Flo’s entourage appeared unmoved, so Mathis laid out the stakes: “He’s the guy coming to make the case for Barack Obama’s reëlection, because he has a problem with working-class white men over fifty. So this is a real important night.”

Over time, Flo honed a routine for private and corporate gigs. “He’ll bring the C.E.O. on and have all the workers and employees and sponsors cheering,” Mathis said. He’ll put his sunglasses on one of the bosses. He’ll shake up champagne and spray the crowd, or hand out roses, pre-positioned in the d.j. booth, for when he does “Where Them Girls At.” It’s all part of what Mathis calls “the formula.” He told me, “The formula is definitely tried and true. It works.” In all, Mathis said, Flo does at least thirty private gigs a year.

At the bar mitzvah, Flo cycled through his œuvre—“Low,” “Club Can’t Handle Me,” “Wild Ones.” He did a reliable bit where he took off his sneakers, autographed them, and handed them to Andrew, who tossed one into the crowd. For the finale, Flo, who has perhaps mellowed since the days when he and DJ Khaled dazzled clubgoers with “Bitch I’m from Dade County,” shouted, “Chicago, baby!,” and a shower of red confetti rained down, sticking to the kids’ sweaty foreheads.

Back in his dressing room, Flo slumped into a Philippe Starck-style translucent chair, towelled off his pate, and slipped into gray rubber slides, to replace the sneakers he gave away. One-on-one, he is soft-spoken, and I wondered how he generates the gusto that the formula requires. “I’ve been doing this for fifteen years,” he said. “I just take it like an invitation to a party. If you come out there and you don’t reciprocate, then it’s just a waste of everyone’s time.”

He takes some pleasure in managing the eccentricities of the cohort that can afford him. He recalled arriving for a gig on a megayacht in Sardinia, and finding children at play on deck. “I’m thinking I’m going to perform for all these kids,” he said. Instead, he was summoned to a quiet section of the yacht and thrust in front of three adults, who were seated patiently at a round table. It was a notable departure from his experience, in 2016, of playing for eighty thousand festival-goers at Wembley Stadium. It was also, he knew, the only way he was getting off that boat with his fee. “I come for a purpose,” he said. “Once I learned that, that’s where the longevity comes in.”

An assistant approached with flutes of champagne. Flo waved him off and asked for a Red Bull. A moment later, the door of the dressing room swung open, and a dozen kids crowded in for the “meet and greet,” as stipulated in the contract. The guests posed for photos—the boys making tough-guy faces, the girls giggling madly—while Flo projected a look of serene forbearance.

It was the look of a man who has done so many privates in Europe, the Middle East, and Asia that he says he feels like “I lived in China and Japan”—a man who has made multiple trips to Necker Island, the private getaway owned by Richard Branson. (“He gets wild onstage,” Flo said.) In the dressing room, Flo asked one of his bandmates, a rapper called Oya Baby, to jog his memory about where they had stayed for the last gig there. “Guana Island,” she said. “It’s known for lizards everywhere. Not far from the Richard Branson island.”

Both of them lingered on one incident in particular: a wedding in Beirut that started under unpleasant circumstances. “The plane had us late, and this guy was so upset,” Flo said. The bride was in tears, and the groom was livid, pestering the performers while they tried to set up. “I was, like, ‘Are you done? Because I’m going to the stage,’ ” Flo recalled. “And then, after I performed, he was so happy!” Flo was not quite so forgiving: “I was, like, ‘No, don’t try to hang out with me now.’ ”

Smokey Robinson still books privates, but at the age of eighty-three he finds ways of conserving energy on the job. Glenn Richardson, the event producer, hired him not long ago, and watched Smokey engage in such protracted patter with the audience that he wondered if patter was all they were going to get. “I went over to the road manager and said, ‘Is he going to sing anything?’ And he goes, ‘Glenn, you don’t tell the vice-president of Motown Records when they need to start singing.’ ”

The tension between the talent and the money has a long history. In ancient Rome, wealthy music lovers had enslaved performers put on private concerts, known as symphoniae—even as Seneca scolded those who preferred the “sweetness of the songs” to “serious matters.” Caligula liked to be serenaded aboard his yachts, and to pantomime with performers in a kind of pre-modern air guitar.

Even geniuses have had to navigate a certain servitude to their sponsors. Mozart fumed about the Archbishop of Salzburg, who “treats me like a street urchin and tells me to my face to clear out, adding that he can get hundreds to serve him better than I.” But some learned to cultivate the sources of capital. In 1876, Tchaikovsky was an unhappy professor at the Moscow Conservatory when he received a letter from Nadezhda Filaretovna von Meck, the lonesome widow of a railway tycoon. Madame von Meck asked him to expand one of his pieces, which, she wrote, “drives me mad.” He obliged, and before long she had put him on a salary and installed him at a villa in Florence. Tchaikovsky wrote to his brother, “N.F. asked me when to send the June remittance. Instead of replying ‘Darling, for goodness’ sake at once!’ I played the gentleman.” But the relationship soured, and the composer had to find new sources of income; he wrote glumly, “It has all turned out to be a vulgar, silly farce of which I am ashamed and sick.”

In the early days of rock and roll, its stars advertised their allergy to materialism. During a press conference in 1965, Bob Dylan was asked, “If you were going to sell out to a commercial interest, which one would you choose?” Dylan’s response—“Ladies’ garments”—suggested that the question was absurd. In a similar spirit, the Who released an album called “The Who Sell Out,” with a parody ad on the cover of Roger Daltrey selling Heinz baked beans. Bands could be shunned for any perceived transgression. In 1985, the Del Fuegos, a New England rock group favored by critics, appeared in a TV ad for Miller beer. Longtime fans revolted. Another band wrote lyrics—“I’d even drink Pepsi if you paid me enough”—mocking their commercial appearance. Warren Zanes, a guitarist in the Del Fuegos, told me, “The general position was: That’s the earmark of a true sellout.” Looking back, though, it seems like the first rumble of a quake along the fault line between art and commerce. “We didn’t want to be fathers of that movement, but in some very small way we were,” Zanes said. “Once it’s the age of streaming, suddenly people weren’t as pure as they thought.”

The advent of Napster, in 1999, not only reduced musicians’ revenues but also scrambled the pieties surrounding art; fans who gleefully downloaded stolen music had to cede some moral high ground. In the coming years, Dylan fulfilled his prophecy and starred in a Victoria’s Secret commercial, the Who licensed a song to Pepsi, and Pearl Jam, which had been so averse to consumerism that it largely refused to make music videos, promoted an album in partnerships with Target and Verizon. In 2011, after the duo Sleigh Bells had its music in a Honda commercial, one member told an interviewer, “It’s almost pretentious to avoid the opportunity, especially in this climate.” Rock, after all, was playing catch-up to the cultural triumph of hip-hop, which had celebrated capitalism ever since the Sugar Hill Gang rhapsodized about a Lincoln Continental, a color TV, and “more money than a sucker could ever spend.”

The forthright attitude toward commerce also became visible in the private-gig market. Doug Sandler, known as DJ Doug on the mitzvah circuit around Washington, D.C., remembers the first time he was told to make room for more famous talent: “They had, as the main act, the Village People.” In 2002, David Bonderman, a Texas venture capitalist, booked the Stones for his birthday, at a reported fee of seven million dollars, and word spread. Jennifer Gilbert, the founder of Save the Date, an event-planning company in New York, noticed that clients were becoming overtly competitive: “They started hearing it more and more—‘Oh, they had this person perform.’ So now someone says, ‘We want something totally unique and over the top.’ ” Over time, the preferences showed a pattern: whoever was popular with young men about twenty-five years earlier was in renewed demand, as a rising cohort achieved private-gig-level wealth. (Current favorites include the Counting Crows and Sir Mix-a-Lot.)

In 2007, on the eve of the financial crisis, the financier Stephen Schwarzman treated himself to performances by Rod Stewart and Patti LaBelle, at a sixtieth-birthday party so lavish that it prompted what the Times called an “existential crisis on Wall Street about the evils of conspicuous consumption.” A decade later, when Schwarzman threw a party for his seventieth—featuring not only Gwen Stefani but also trapeze artists, camels, and fireworks over Palm Beach—it barely protruded above the tide line of the Trump era.

As the market grew, there was an inherent friction between the instinct to show off and the instinct to keep quiet. In 2012, shortly before the Silicon Valley entrepreneur David Sacks sold his company Yammer for $1.2 billion, he threw a costume party for his fortieth birthday, where guests were under orders not to leak details. The embargo was broken by the hired entertainer, Snoop Dogg, who posted a photo of himself posing with the birthday boy. Sacks was wearing an eighteenth-century waistcoat, a wig, and a lacy cravat, in the mode of Marie Antoinette. The party slogan was “Let Him Eat Cake.”

Musicians, on the whole, don’t get into the business because they dream of playing for tiny audiences, under the shroud of an N.D.A. Hamilton Leithauser, who helped found the indie band the Walkmen before launching a solo career, recalls peering out one night into a dark club filled with “older, heavyset Philly finance guys.” He had been hired as the dinner entertainer at a business conference. “They must have spent a million dollars on the party, and they had pulled in all these huge leather couches and spread them out throughout the room.” The remoteness was not only physical, he said: “The closest person is probably thirty feet away, and it’s a banker eating a lobster tail.”

David (Boche) Viecelli, a veteran booking agent in Chicago, has tried to help musicians navigate unfamiliar territory. Viecelli, who founded the independent agency the Billions Corporation, has represented Arcade Fire, Bon Iver, and other big acts. I asked him how musicians react when they get a private offer. “Every artist always thinks, Well, this is either going to be a total shit show or at least a drag,” he said. “That goes all the way up to when you have Beyoncé going to play for some emir.”

Despite all the luxuries, “corporate events can be sort of soul-destroying,” Viecelli said. “It’s not really an audience. It’s a convention or a party, and you just happen to be making noise at one end of it.” When musicians are uncertain, he has some reliable tools to help them decide: “If you can say, ‘Hey, I’m going to go have a bad time for an afternoon, but it’s going to pay for my kid’s entire college education,’ then that’s a trade-off I think most responsible adults will make.” But these days he has less persuading to do. “If you talk to a twenty-year-old in the music business now, and you bring up this idea of the weirdness of doing corporate events, they’ll just stare at you, like, ‘What are you talking about?’ You might as well say, ‘Don’t you feel guilty for eating pizza?’ ”

The realities of making a living in music have changed radically in the past decade or two. Viecelli used to counsel emerging artists to plan for a long-term career: “It might not necessarily make you incomprehensibly rich, but it would give you a way to continue to make music the way you want, while doing it as a full-time job and being secure.” In the streaming economy, audience attention is shallow and promiscuous. “A kid could know a track inside out, listen to it a thousand times that summer, and not know the artist’s name. They’re just surfing along the wave of whatever’s getting spit out,” he said. “The truth is, now young artists know they’re going to have—even if they’re successful—two to four years. Maybe. And so that means that they want to monetize everything as fast and hard as they can.”

Given the pace of that churn, artists tend to obsess less about impressing A. & R. executives than about elbowing their way onto top-ranked playlists, with names like RapCaviar and Songs to Sing in the Car. “They know there’s this giant unthinking audience that just keeps streaming these playlists and racking up those counts,” Viecelli said. “Everything is geared towards treating artists essentially as disposable.”

Even as streaming has diminished the returns on recording, social media has created an expectation of accessibility. Fans no longer assume that their favorite artists are remote figures. Viecelli told me, “I’ll get e-mails from people saying, ‘I live in Philadelphia, and I see that they’re coming to town, and my daughter is a big, big fan. Could you stop off at our house to play a few songs?’ ” He laughed. “It’s, like, ‘Are you nuts?’ But if that person says, ‘And I’d be happy to pay five hundred thousand dollars for the privilege,’ well, then, actually it begins to change.”

In the spring of 2015, Steely Dan was hired to play a fiftieth-birthday party for Robert Downey, Jr., in a converted airplane hangar in Santa Monica. Steely Dan didn’t do many privates, but Downey had endeared himself to the singer Donald Fagen. Downey, who had built a thriving late career playing Iron Man in Marvel movies, was celebrating with friends from Hollywood. “Phones were taken away. Downey came up and sang ‘Reelin’ in the Years’ with us,” Michael Leonhart, who was playing trumpet that night, recalled. When the evening’s other band, Duran Duran, took the stage, Leonhart quickly realized what it meant to generate stadium campiness on a small scale: “Simon Le Bon has his back to the audience. Then he turns around, the drum machine starts, and he goes, ‘Is anybody hungry—like the wolf? Two, three, four!’ And I’m, like, ‘Oh, my God, this guy gives good privates.’ ”

Leonhart, who has also played private gigs with Lenny Kravitz, learned to expect odd moments when the disparate tribes of cultural capital and financial capital meet: “Either they’re in awe of your group or you’re the paid servant. You’re never sure which meal you’re going to get, or which entrance you’re going to use. When push comes to shove, it’s a caste system.” He conjured a controlling host: “I love what you’re wearing. Can you maybe button up that shirt one more button? My great-grandmother is here.” When hosts try to merge friendship and labor, though, the result can be awkward. Leonhart said, “Even if it starts off well, there’s usually a fart-in-church moment, where someone is trying to be cool, as opposed to just owning it for what it is: You paid a shitload of money—enjoy it.”

Over time, artists have become more willing to accept proximity. First, they embraced the meet and greet, earning extra money on top of a concert ticket in exchange for a photo and some effortful bonhomie. (Scholars of the workplace call this “relational labor.”) Privates have extended that concept by several zeros, though the underlying principle remains the same: a man who books Snoop Dogg for a private party is probably a man who would like to smoke a joint with Snoop Dogg. (Snoop avers that he has, indeed, smoked weed while working a bar mitzvah.)

In the taxonomy of paid performances, as in other parts of life, the money tends to vary inversely with dignity. Headlining a regular concert, known to professionals as a “hard ticket,” pays the least; a festival, or “soft ticket,” pays more, because it is usually flush with corporate sponsorship money. Privates pay the most, with the added bonus that they don’t violate “radius clauses,” which venues impose to stop bands from playing too many shows near one another. Thus, the modern dream scenario: take a million dollars for a holiday party on Tuesday, then play the Beacon Theatre for half that sum on Thursday night.

Ian Hendrickson-Smith is a saxophonist with the Roots, who have played privates around the world, including at Obama’s sixtieth birthday on Martha’s Vineyard. (“They put me in a tiny plane that was barely a plane. I was terrified,” he said.) Hendrickson-Smith also releases albums under his own name, and he has watched the market change. “The largest distributor of actual physical records in the United States was fucking Starbucks,” he said. “I used to get some nice checks. Now I put out a record and it gets streamed a ton, but my check from Spotify is, like, sixty-five cents.” A 2018 report by the Music Industry Research Association found that the median musician makes less than thirty-five thousand dollars a year, including money that’s not from music.

Viewed in that light, private gigs can start to feel like something close to justice. For years, Hendrickson-Smith toured with the late Sharon Jones and her band, the Dap Kings, and they often jetted overseas to play tycoons’ weddings. “The second we’d hear the W-word, our price tripled immediately,” he said. But he also learned that relying on private money exposed him to a new type of captivity. He once played a private party in New York where the host had hired little people, costumed as Oompa Loompas and as members of Kiss, to serve drinks. “I was mortified,” Hendrickson-Smith said. “But I couldn’t leave. It was brutal.”

There are ways to contain the risks. Adam Harrison, who manages Chromeo, Fitz and the Tantrums, and other acts, politely reminds private clients to limit their requests: “I’m O.K. doing a callout, but not ‘To Gary in sales, who had a great year!’ ” Moreover, Harrison said, he does not encourage his acts to put aside their values for any gig. “I’ve had bands not play Saudi Arabia privates,” he said. Another longtime manager told me that none of his acts would accept an invitation from the conservative fast-food chain Chick-fil-A, except for his one Christian band: “They don’t give a fuck. It’s right in their wheelhouse.” The ideal situation, the manager went on, is when a client is especially wedded to one act—say, the band that was playing on the Starbucks sound system at the moment that a couple met, or a pop star who seems perfectly aligned with a company’s brand identity. “When it’s a specific thing like that,” he said, “everybody smells blood.”

You don’t have to be a musician to wonder if musicians are held to an unfair standard in an era when painters unabashedly sell work to barons of insider trading, when former Presidents (and almost-Presidents) get hundreds of thousands of dollars for Wall Street speeches, and when college athletes license their likeness to the highest bidders. Call it an “evolution in the culture,” a prominent music producer told me. He apologized in advance for invoking Donald Trump, then said, “Look at who almost half the country voted for in ’16: a guy who, if you charge less than you can, because you have qualms about playing something strictly for the élite, would look at you and say, ‘Loser!’ And an amazing number of people would agree.”

“So you’re writing about the star-fuckers who host these things?” Anthony Scaramucci asked, when I called him this spring. He was, in fact, describing himself, but he did not seem offended by my request for an interview. “I’m a wholesale provider of this shit,” he said. “I understand this shit.”

Long before Scaramucci became a household name for his eleven-day stint in the Trump White House, he was known as a hedge-fund manager who hosted a business conference called SALT. To attract attention to the conference, he booked private gigs by Maroon 5, Lenny Kravitz, Will.i.am, Duran Duran, the Chainsmokers, and others who might please a roomful of mostly middle-aged finance types. His conferences tap into the power of aspirational proximity; in other words, he helps well-paid shmegegges get close to their heroes.

“We’re in love with fame,” he said. “Our entire society is addicted to it.” The addiction extends to the wealthiest among us, he went on. “But let me give you the bad news for rich people: They can only go four places. They can go into the art world, or private aircraft and yachting, or charity—naming buildings and hospitals after themselves. Or they can go into experiential.” He adopted the voice of a big spender: “ ‘I’m super loaded! I have a Rolls-Royce!’ Well, fuck that. There’s ten thousand of them. But if I tell you, ‘You are one of a kind!,’ now you’re special.” As we spoke, he was stuck in midtown traffic, which occasioned a mood of patient contemplation. “You’ve got to think about it as a pyramid,” he said. “The widest part is eating at McDonald’s. The narrowest part is ‘I paid two hundred million for the Basquiat.’ Because that’s one of a kind. I’m taking a piece of the immortality that artist created, and I’m owning it. Freud said we’re ultimately hysterical because of our own demise. This is why we do these things. I have to prove that I’m really living.” He paused to let that sink in, and then returned to the voice of the big spender: “So Andrea Bocelli is going to sing at my daughter’s event.”

To turn Scaramucci’s abstractions into a gig requires a producer who can line up the money and the talent—a mix of diplomat and shrink, who specializes in what’s known as “talent buying.” Danielle Madeira, a talent buyer and producer in the San Francisco Bay Area, has come to expect that wealthy hosts will have trouble accepting the limits of their power: “I have to explain this to clients—you have agreed to make this offer, but that doesn’t mean they accept the offer! It’s not like you’re buying something at Target.”

J. B. Miller, the C.E.O. of Empire Entertainment, an event-production company, conducts due diligence on hosts before making an offer to a star. “I have to provide a lot of biographical material on not just the principals but who is in the room,” he told me. Miller recalls a surge of bookings during the dot-com boom. “The underlying business may or may not have ever had a possibility of making it, but, when you have artists standing up there under your logo, the world thinks, Wow, look at their stature! They must have so much money.”

There is wariness on all sides. When Miller was starting out, three decades ago, he booked Aretha Franklin for gigs in Manhattan and the Hamptons, and alongside the Kentucky Derby. Franklin, like many Black artists of her generation, had grown wary of being cheated, so she demanded that her management square up in cash for every gig. “We’d sit down before the show and count it out,” Miller said. He also recalled doling out cash to Ray Charles, Etta James, and James Brown. “You’d settle that, and then they’d go down to the stage.”

Miller bristles at the question of whether patrons, and artists, might benefit more people by steering that money and talent to occasions that are open to the public. In San Francisco, for example, the late billionaire investor Warren Hellman endowed a free festival, Hardly Strictly Bluegrass, which draws half a million people to big-name concerts in Golden Gate Park. Miller sees no reason that the two kinds of events can’t coexist. “When did music cross the Rubicon into a public service?” he asked. “You can certainly see that artist that you love when they come to a town near you. And, if you have the means, you can also have them at other times.”

Peter Shapiro, a promoter who owns the Capitol Theatre and the Brooklyn Bowl, argues that this kind of spending is at least a better use of mega-wealth than other indulgences. “The privates are good for the talent, good for the venue, good for the staff,” he said. “A private with great talent means hundreds of your friends can join you. They can’t always join you on a yacht or in the Maldives.”

On a crisp spring night on the southern tip of Manhattan, Flo Rida was backstage once more. This time, he huddled in a darkened hallway with his dancers and the d.j. and Int’l Nephew, their arms laced around one another, as they murmured a prayer. Then they lined up in a loose stack behind the door that separated them from the stage.

On the other side, in a cavernous ballroom bathed in purple light, about four hundred people with matching lanyards were celebrating the twenty-fifth anniversary of a private-equity firm. It was business casual, with the occasional bow tie and ball gown. A sushi buffet ran the length of one wall. The venue, Casa Cipriani, occupies a restored Beaux-Arts ferry terminal that also includes a hotel and private club, which offers suites with cashmere-lined walls, easy access to a helicopter pad, and fastidious attention to service. Guests are asked to choose which type of Italian bedding they prefer, cotton or linen.

At the lectern, two of the firm’s leaders were holding forth. A gray-haired man in a gray plaid blazer praised his colleagues’ delivery of “industry-leading returns for our limited partners,” and thanked attendees for various feats, including “five hundred million in proceeds at a 5.5x multiple on investment capital” and enduring “awful six-hour golf rounds with me.” As showtime approached, a partner in an elegant black-and-white gown told the crowd, “With pride in our hearts and sushi in our mouths, let’s celebrate.”

The partygoers had not been told who the headline entertainer would be, and some were quietly hoping for Springsteen. When Flo charged out from backstage, there was a brief vacuum of silence. But he plunged ahead into “Good Feeling,” a thumping ode to success, with references to a Gulfstream, a Bugatti, and a Maybach. (“Talk like a winner, my chest to that sun / G5 dealer, U.S. to Taiwan.”) The crowd began to fall in, and Flo showed a rowdier mode than he had at the bar mitzvah. “Who wants some shots?” he shouted, holding up bottles of vodka and tequila. There was a nervous titter; a gentleman in a bow tie craned his neck for a look, and then some of the younger guests stepped forward to drink from bottles held in Flo’s outstretched hands. The mood in the room started to evolve fast.

I was permitted to attend as long as I promised not to name the firm. It was a private gig, at a private club, for a private-equity firm—an entire arena of American commerce defined by self-conscious exclusivity. I’ll call the firm Equity Partners. As the night wore on, Flo developed a call-and-response with the crowd. He’d shout, “What happens at Equity Partners—” and they’d shout back, “Stays at Equity Partners!”

By the time Flo was rhapsodizing about the pole dancer in “Right Round,” the formula was in full effect: Flo put his sunglasses on an executive, and the crowd howled, while the man lurched around in awkward ecstasy. When the performers got to “Where Them Girls At,” Flo grabbed the roses from the d.j. booth and doled them out to giddy recipients. He peeled off his vest and stalked the stage, his naked torso showing tattoos of Ray Charles, James Brown, and Sammy Davis, Jr. Before long, there were so many men and women clambering up onstage that the dancers, in their mesh leggings and bikini tops, had to fight to be seen. Flo kept pouring from a bottle of Grey Goose, and people in the crowd kept approaching to tip their heads back, blazers thrown open, lanyards askew.

It was hard to tell which side—Flo or the investors—was more amused by the scene of communion between distant cousins in the family of wealth. When the show was over, the junior analysts staggered off in pairs, while the middle managers hustled to Metro-North. Flo returned to his dressing room, which was bustling with assistants, hangers-on, and aspiring friends. The performers were swapping tales from the night—of “the elderly woman in the front,” at stage right, who went bananas during “Wild Ones.” “She got her groove back in that exact moment,” Oya Baby said. “She was, like, ‘Me? I’m wild! ’ ”

It wasn’t all that different from Flo’s big years; it’s just that the audience was smaller and the fee larger. Seven years after his last Top Ten hit, the crowds still get loopy when they hear a song from their high-school prom, and some of the erstwhile club kids are now entering middle management, with the power to book the entertainment for the holiday party.

Carts of food arrived—truffle fries, grilled fish, champagne—but Flo was nursing a bottle of Pedialyte, the rehydration secret for middle-aged stardom. The next morning, he was flying off to St. Louis, followed by Miami, Vegas, Arizona, Minnesota, and Vegas again. I wondered how long he planned to keep up his pace. “The thing is, people love to feel loved,” he said. “So it doesn’t matter if you’re doing this gig or that gig. It never gets old.” He turned to the side, to oblige one of the event planners with a selfie. The first time we met, he had confessed to the addictive pleasure, as ancient as Caligula, of watching people watch you. And, of course, there was the motivating question that would be familiar to his private audiences: “How much money is enough money?” ♦