Seinfeld probably could not have made it on NBC today. The sitcom, helmed by a young comedian whom few people had heard of, struggled for years to find an audience. But after a while, this little “show about nothing” became the most lucrative sitcom property in the history of network television. It made everyone involved in its production inconceivably wealthy. It struck a deep chord with the American public that remains resonant today.

Why?

Ask Seinfeld fans to list their favorite episodes. You’ll get a wide variety, too wide for me to catalog properly. So I’ll list a few examples, some of which you’re likely to recognize.

• Jerry asks Elaine to figure out if his new girlfriend’s breasts are real.
• George gets admission to a hip nightclub by pretending to have dated a model (whose photo he carries in his wallet).
• George buys a cashmere sweater for Elaine at a tremendous discount because it has a prominent red dot on it.
• Elaine tries various means to trick a Chinese delivery place into delivering to her apartment, even though it’s out of the area they serve.
• Kramer poses as the head of a corporation (“Kramerica”) to get an intern from a local college.

And so on.

The tone of the episodes ranges from “comedy of errors” to cheap sexual humor. All four characters are guilty of scheming, selfishness and dishonesty. And none of their schemes pay off.

In each of those examples – in fact, in almost every episode of Seinfeld – a main character’s scheme to get ahead backfires. Jerry gets found out and his girlfriend breaks up with him. George gets caught and loses his job. Elaine gets discovered and is mortified in front of a friend, boyfriend or coworker. Kramer’s plans fall through and he ends up in some ridiculous situation. It’s a formula.

Seinfeld is about people trying to hustle and failing.

A true hustler hustles because he wants that little extra, or because legal means of work are either unappealing or unavailable. As Biggie put it, if you want to get out of the hood, “you’re either slingin’ crack rock / or you got a wicked jump shot.” But the characters on Seinfeld hustle out of a blend of guilt and shame. They fear that they’re the least savvy people in the world: missing out on discounts, bonuses or a satisfying life. Note how Jerry laughs at George after he confesses to taking his car to a dealership for repairs. These people hustle, not out of need, but out of neurosis.

And yet they keep failing. The stars of Seinfeld are the opposite of hustlers. They are customers.

If a hustler is a guy who always haggles, the customer is the guy who always pays list price. If a hustler is a guy who fast-talks, a customer is a guy who can be fast-talked. A hustler shops around; a customer orders in. A hustler keeps hustling; a customer grows accustomed.

Okay, so Jerry, Elaine, Kramer and George don’t have any game. Not exactly shocking. And yet, for 9 seasons, they kept trying. They never stopped trying to scam their way out of work, con their way into relationships, or lie their way out of trouble. Never. Even after every previous attempt at either selling a sitcom to NBC, getting rich off of recycled cans or sneaking a bite of Mr. Peterman’s antique wedding cake had failed in a humiliating fashion.

http://www.youtube.com/watch?v=LHchl4AxsE0

Why did they keep trying? What was the tragic flaw – the hamartia, to touch Aristotle – that kept these characters from realizing why they could never succeed?

Let’s go back to the definition of a hustler. Hustlers live by their wits. They scheme for something extra. And they always come from the social underclass. Remember, someone who’s conniving, greedy and powerful is a villain. Someone who’s conniving, greedy and poor is a sympathetic hero, or at worst a lovable rake.

Are the characters on Seinfeld poor?

Jerry and Kramer live in neighboring one-bedroom apartments in the Upper West Side of Manhattan at the height of the mid-90s real estate boom. Elaine moves a few times, but she also lives on the island. George’s fortunes rise and fall the most: he has a city apartment, then he has to move back in with his parents. But he still bounces from one rich job to the next: real estate, then playground equipment, then eventually working for the New York Yankees – the most lucrative sports franchise in the world after Arsenal.

The characters on Seinfeld are not poor. In fact, I might conservatively say that four white people in their 30s who lived in roach-free apartments in Manhattan between 1989 and 1998 are as rich as it is possible for human beings to be. They are in the top 1% of the top 1% of ten thousand years of humanity. The difference between Jerry Seinfeld and Warren Buffett, as viewed by the richest person in France in the 14th century, is infinitesimal.

The story of Seinfeld is the story of four rich people who don’t know how good they have it. They think they have to keep hustling in order to make ends meet, when in fact they don’t. They think that their conniving makes them sympathetic, when in fact it makes them look petty. They’re displaying the relentless striving of the urban poor without any of the entrepreneurial savvy. The end result is pathetic. That’s why Seinfeld is a comedy.

It’s no coincidence that Seinfeld and gangsta rap both blew up in the 90s. There’s no other period in which they could have arisen. Seinfeld only works in contrast to the hustler lifestyle: all of its jokes turn on successful people trying to hustle and failing. And the hustler lifestyle came to prominence in the 90s, thanks to gangsta rap. Jerry Seinfeld and the Notorious B.I.G.; George Costanza and Tupac Shakur. They circle each other like yin and yang in a constant state of dynamic tension.