They talked, almost wearily, about unsuccessfully trying to pick up the waitresses at the bar down the block; about the best restaurant bathrooms in which to blow cocaine; about a prep school friend who’d been pulled over for weaving along a Connecticut road and acted more drunk than he really was, hoping the cops would just write him up and not search him for the bag of weed he’d stuffed in his crotch. They had these brittle, smirking laughs. My girlfriend and the heiress came back with drinks for everyone; we sat around with the oldest money there is drinking Coors Light on ice, out of mugs. Somehow, I had expected martinis.

It was a strange evening. Demographically, there wasn’t much to separate my own background from these heirs–many of my friends had grown up pretty rich, in the same zip code, had gone to the best private schools. My friends and I were the children of doctors, lawyers and bankers–competitive, high achieving kids. But we were also only second- and third- generation Americans, the children and grandchildren of Jewish and Asian immigrants, and we had been raised with the understanding that we had been born during the upswing of our family epic, bound to higher achievement than even our own (by any standard, inordinately successful) fathers and mothers. We also had no big trust funds waiting for us, and so had to work for our livings. The kids at the party, by contrast, had grown up believing that they were presiding over the decadent decline of their families, and, without the grit to compete academically with the aspirants and strivers, ended up chasing the depravity sweepstakes. The Coors Light, the weed in the crotch, the coke in the bathrooms, the banter about slutty waitresses: These were all self-conscious signals that they knew that they represented families and fortunes on their downswing, and that they were determined to live that decline to the fullest.

The culture I glimpsed in that apartment is now playing out on gossip pages and TV screens. America has become rather suddenly obsessed with the antics of young, wayward socialites who dance topless on nightclub tables and pose shamelessly for publicity cameras at every Hollywood premiere and Manhattan after-party. There are near-daily updates about Lionel Ritchie’s daughter Nicole trying to quit heroin and getting into fights at New York nightclubs; Johnson & Johnson heiress Casey Johnson indulging in plastic surgery and getting into fights at the same nightclubs; and Paris Hilton doing virtually everything and anyone. (Last November, millions of Internet-capable Hilton fans had the pleasure of watching a home video of Paris and a then-ex-boyfriend having bored, flamboyant sex–in one magnificent moment, she demands that he pull out so she can answer her cell phone.)

Those who wish for an even closer look–if that’s possible–at the lives of our decadent elites can now choose from three documentary programs dedicated to exploring the psychologies of the young and extremely wealthy. The most successful, ratings-wise, has been FOX’s show “The Simple Life,” billed as a non-fiction version of “Green Acres,” which sends Paris Hilton and her best friend, Nicole Ritchie, to spend two months on an Arkansas farm. MTV has “Rich Girls,” which documents the shopping-and-sentimentality-heavy summer before college of New York heiresses Ally Hilfiger and Jamie Gleisher. Then there’s Born Rich, a documentary which debuted at Sundance this summer and is now showing on HBO, in which a 24-year-old heir (Jamie Johnson, of the Johnson & Johnson fortune) interviews more than a dozen of his friends, all also heirs, about growing up very rich. They talk about everything from the cut of a fine suit to the blind chance of their social station to, defensively, the need to set up safeguards like prenuptial agreements to protect their fortunes from too-quick erosion. The nation’s current super-elite, one and two generations removed from the middle classes, understands that class status rests on the thin ice of dumb luck.

Decadence amongst the inheritance class is nothing new. It has been a repeated literary theme from Prince Hal in Shakespeare’s Henry IV cycle to Sebastian Flyte in Evelyn Waugh’s Brideshead Revisited. But there have been several cultural shifts in recent years that explain why we’re seeing so much dissolute wealth in our pop culture. The inheritance class, following the two biggest economic booms in American history, is bigger than it has ever been. At the same time, the children of this class, for all their financial advantages, now operate with a profound aspirational disadvantage. Quite simply, it has become harder and harder for them to find something useful and rewarding to do with their lives.

In previous generations, children of the super-rich had respected slots at the top of certain American institutions set aside for them. After an all-but-guaranteed education at Ivy League schools, they could expect to work at family-owned corporations, or investment banks to which their fathers had ties. They would serve on the boards of foundations and other charitable organizations, and by dint of their wealth, would host parties, salons, and other social gatherings that would get them written up in the newspapers. Today, these slots are no longer reserved for the children of the rich but are open to competition, and that competition is fierce. Legacy status guarantees only a few points on a Harvard application. Shareholders have little patience with sinecured executives who don’t perform. Even high society in New York and Los Angeles is no longer dominated by heirs but by professional publicists, club promoters and pop celebrities who throw the most glamorous and coveted parties, to which the Vanderbilts and Rockefellers try to wrangle invitations.

As meritocratic competition has expanded upwards, undermining the sheltered workshops that once gave rich kids outlets for their energies, the mentality of these heirs has changed. For better or worse, they’ve internalized meritocratic values, which are really just broad American values–in particular, a disregard for status gained by dint of one’s birth rather than by virtue of one’s talent. This disregard manifests itself in various forms of self-loathing, apparent in almost every scene of shows like Born Rich and “Rich Girls.” This generation of rich kids is perhaps the most unhappy in history. And their peculiar predicament has prompted an en masse attempt to experience, in ways both admirable and depraved, what life is like outside the bubble of their privilege.

One of the reasons that these shows are appealing and have been successful is that they give the viewer a chance to sneer at these loopy, out-of-touch, dysfunctional rich people. But that doesn’t explain the appeal entirely. The chance to sneer might keep viewers tuned in for an episode, but likely not a season. The reason people are watching may very well be that the characters are simply more sympathetic and interesting than the shows’ publicity make them out to be.

Born Rich is the most self-consciously literary and also the best of these programs. In interviews, Johnson, the film’s director, has said that his goal was to document the “voodoo” of inherited wealth, the pathologies and stunted ambitions of growing up very rich. Because Johnson is an heir himself, he gets a rare level of candor and depth from his interview subjects, who are also frequently his friends. Some of them, like the textile heir Cody Franchetti, are interested mostly in detailing the prerogatives of vast wealth–the great suits, the fab polo horses. Others are more thoughtful and complex, like Johnson’s childhood friend Josiah Hornblower, an heir to the Whitney and Vanderbilt fortunes who took two years off from college to work as a machinist in the Texas oil fields, and, improbably, Donald Trump’s daughter Ivanka. The collective portrait that emerges from these more intelligent rich kids is one of guilt and unease. They’re a little bit embarrassed by being so wealthy and have a powerful, discomforting suspicion that their station has restricted the options open to them.

This theme runs through these shows, expressed sometimes in touching, sometimes ludicrous ways. There is a moment, majestic in its own way, in the second episode of “Rich Girls,” the one in which Jamie, the unattractive, sad and shallow rich girl, slumps against a big wood staircase in someone else’s house and gives the camera a look of impossible fury because the boy she thinks is cute is kissing another girl five feet away. To viewers, this is ludicrous: The boy is far more attractive, mature and intelligent than Jamie, way out of the league, and, besides, the girl is his girlfriend–and Jamie can’t compete with her either. But Jamie’s frustration is positively making her quiver. Three episodes later, she’s still talking about the same event.

Part of her frustration stems from a rich girl’s sense of frustrated entitlement, an inevitable coming to terms with an object she wants but can’t have. But there is something more complex going on here, too, which lends the show its propulsive tragic theme. We know from her previous conversations and escapades that Jamie is beginning to see her life as a closed loop. She knows she is not a success at school. She tells us that she knows her tastes are juvenile and that she is far more spoiled, dependent, and immature than other kids her age. And she knows, too, that she is no great shakes at romance, being unattractive to most of the young men in her circle. Everything she is likely to have, she tells the camera and her friends again and again, comes down to the money she was born into. The dominant image of an inescapable future, for Jamie, is the Park Avenue Mom, spending her days walking her dog, talking on the phone and doing little else with her life. Jamie knows this is not a satisfying life, she tells Ally in the second episode, but she believes that’s what she’ll become.

The rich kids interviewed in Born Rich and shown on “Rich Girls” have, far more than any other children I know, a painful awareness of the trajectory of their lives, and the stereotype of their social station. They know how rich kids are typecast: lazy, ineffectual, their wealth and family name the only source of their success. And so each time they fail at ventures which are not dependent on their wealth or family name, even when they are ventures that anyone would fail at, like trying to date someone far out of your league who already has a girlfriend, they become more convinced that they are bound to enact that stereotype, that there is no way out. When they embrace that stereotype, they become like the heirs I met through my college girlfriend, passionlessly trumpeting the details of their decadence. This tension is what gives these shows their edge, and the characters their vulnerability and humanity: Their stories are pitched by the television networks as comedies, but to the rich kids themselves they are living classic tragedies, trying, and usually failing, to find a way to deny the inevitability of a sneered-at existence.

For those rich kids smart and aware enough to recognize it, these can be debilitating circumstances. It’s the dilemma suffered by a close friend of mine, the only super-rich kid I knew growing up. His parents, both born in India, weren’t socially prominent in the same gossip-pages way as parents of the kids from these three programs, but they were just as rich and successful, and his ancestors have been among India’s wealthiest families for centuries. My friend also had something most of these heirs don’t: a vital and active mind. I remember in particular an astoundingly clever and quick, off-the-cuff interpretation of his, from our twelfth grade European history class, of how Gladstone and Disraeli might have debated the merits of incorporating former Soviet states into the European Union. In a class full of grinds that sent more than eighty kids on to Ivy League schools each year, he finished first, effortlessly, and sailed through Harvard with equal ease.

But, out of school, starter jobs in every profession weren’t glamorous enough, paid too poorly, and were generally just much less exciting, relevant, and cool than the way he had been living his life so far. What he really ought to have done was go to grad school, but the life of a young academic simply had no pull for him: Why would he want to spend 15 years working at some state school in the Midwest, grading bad papers and teaching uninterested students, when even if he never worked a day after college he could spend his time eating at the finest restaurants in New York with the most glamorous people and boating on the weekends in Long Island Sound? He made a few half-hearted stabs at investment banking (what his father, raised equally rich, had done), but didn’t have the interest or energy to compete with the kids whose whole lives depended on how fully their work pleased the managing director. He spent a few months working on a start-up in L.A., but found he had little interest in the busier parts of small business work, and passed his weeks contriving to spend his weekends in Rome and driving up and down the Pacific Coast Highway in rented Lamborghinis.

Soon my friend was back in New York. For a while, he tried to give in to the prerequisites of the born rich, tried to set himself up as a social mover-and-shaker in New York, out every night, spending a thousand dollars a pop to get a booth and bottles of booze for his crew at clubs. His credit card bills averaged twenty thousand a month. He wasn’t particularly successful at this either: He had spent his life cultivating a patrician manner and approach to things, and to be successful in New York, even at going to parties, demands a scrappy, working-class energy. He furthermore ran up against a sort of immovable fact: Celebrity and energy are far more important than simple cash in throwing the hottest parties, making it on the club scene. I was working as a newspaper reporter in Philadelphia at the time. He would call me from New York around midnight on Tuesday and Wednesday nights, so excited, and tell me to meet him at a particular club. “Dude,” I’d say, “I live in Philadelphia, remember? I can’t meet you in Tribeca tonight.” When I did see him, he’d spend the evenings telling me how insincere his new friends in New York were, and then, very late, we’d go back to his parents’ gorgeous apartment, where he lived, and he’d tell me long stories about Indian history, and linguistics. He was doing worse and worse, seesawing back and forth between a kind of tragic desperation and a forced come-what-will bonhomie. I once got a call from him before I went to work: “I am observing the surfing at Biarritz,” he said, “and it is very sad.” He made a poor romantic.

Someone eventually prevailed upon my friend to go to business school, where he is now. It has been difficult to watch him thrash about while far less talented classmates of ours succeed, and though there are certainly many reasons my friend has had a difficult time of it so far, there is a certain oppressiveness about the fact of his family’s vast wealth and success which has colored every choice he has made. Going to grad school or going to work at an investment bank or a newspaper out of college doesn’t seem like a sacrifice to most of us, but an opportunity. For my friend, who couldn’t hope to earn by working what he had simply in return for existing, it meant giving up a life of nearly unmatchable glamour and excitement. Where I, coming out of college, saw chances everywhere, he saw trade-offs.

None of this is meant to excuse the idle rich for being idle. The instinctive response of most viewers to much of what is on offer from these programs is to want to shake these spoiled kids by their shoulders and say, “suck it up and start working at something, like the rest of the world.” The popular scorn for the born rich is understandable, the stereotype mostly on target. But this thrashing about, looking for a way out that both my friend and the kids in these shows have gone through does explain in part why this generation of rich kids differs from previous ones.

There is a scene in Born Rich in which Jamie Johnson asks his buttoned-up father, more or less, what he ought to do with his life. His father, who himself has never worked a day in his life, suggests that Jamie make himself useful by joining some charitable organizations and figuring out how to productively give some of his money away. Jamie presses further: What if he doesn’t want to do that, what if he wants to have a career? His father looks confused, then suggests that Jamie could also take up a hobby, “like collecting old maps.”

One might think that it ought to be a simple thing for Jamie to take his father’s advice about a career in philanthropy. After all, that’s how extraordinarily rich young people have long found meaning in their lives, from the Rockefellers to the Fords. And some heirs still do so today, such as John Walton, who inherited the Wal-Mart fortune and used the money five years ago to endow the Children’s Scholarship Fund, which each year sends 34,000 poor kids around the country to top private schools, tuition-free. There is no doubt that the social utility of the vastly wealthy resides in their ability to fund, through charitable endeavors, social programs that the government is unwilling or unable to take on. But from interviews in Born Rich, it seems that the current generation feels like such efforts are still too much in the bubble, merely another way of piggybacking on your family’s accumulated fortune.

It’s an understandable feeling, but not good news for society as a whole. Now that we’re saddled with the largest, wealthiest, and least-happy inheritance class in America’s history, it seems like a good idea for someone to come up with something useful for these people to do with themselves and their money. At the very least, shows like Born Rich are good advertisements for a return of the estate tax, which the great philanthropist Andrew Carnegie favored as a spur for the rich to spend their wealth on good works during their lifetimes, rather than lose it to the government.

Uninterested in lives of noblesse oblige, unwilling to compete in the meritocracy, and unable to find satisfaction in merely spending their bequests, rich kids today seem to want nothing more than to escape the bounds of their privilege. This explains, I think, the mass class-mixing that we’re seeing on TV–a phenomenon playing out in both good and bad ways. Some rich kids, convinced that they can’t break out of the stereotype of decadent decline, are simply trying to live that decline to the fullest, more or less slumming. (Some, like Paris Hilton, take it a half step further, using the public image of the morally lapsed wealthy to leverage a crass and grimy half-fame, living archetypes of rich kids gone to seed.) For others, class-mixing is a real form of education, one that both toughens and tenderizes the world-view of these heirs, who, because of their wealth, have enormous potential for influence. Watching Josiah Hornblower struggle gamely to figure out how to use his wealth for good, you have the distinct sense that his two years in an oil field will prompt him to some sort of socially beneficial action.

And that sense that a well-lived life must include attempts to understand how most people experience the world is one of the heartening themes to emerge from these programs: Whatever else they are, most of these kids have at least the ambition to be in touch with common people. The protagonists in these programs, like my friend, profess a need to be useful–as Ally Hilfiger says, “to do something.” They feel like their wealth keeps them locked up and artificially divorced from middle-class people with whom they have a lot–values and ambitions–in common. Another whimsical, twenty-odd year old rich party-boy, George W. Bush, found his public calling after comprehending, in part through his religion, just how much he was like everyone else. A feeling of frustration, and sympathy with the masses, may be a useful start.

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Benjamin Wallace-Wells is a staff writer at the New Yorker.