The demise of the modern playboy

One way to describe the American Dream is the hope that, here, it’s possible for more people than ever to act as if they’ve benefited from more privileges than they have. Here, the gentleman is a character type to rival the playboy, because the gentleman is more universal but also more demanding. There’s more pride in being a gentleman. There’s more sustain. But today, that’s less and less so. Gentlemanliness doesn’t carry the cachet it used to. In the absence of reciprocation and appreciation, it’s harder to maintain. Even a gentleman is sometimes forced to look into the mirror after a long day of being a gentleman and ask, why bother?

The increasing bifurcation of society into a winner class and a loser class is bad news for the gentleman as a character type. The triumph of casual wear in public bums the hell out of the gentleman. The idea that you have to read a magazine—or, worse, should want to—to figure out what things to buy in order to present as a gentleman bums the hell out of him, too. The winners and the losers alike are both way more actorly than the gentleman wants to be. Yet the kind of authenticity given off by the winners and losers alike is far too crass and vain for the gentleman. Truth be told, when he’s trying to fall asleep at night without the aid of legal or illegal drugs, the gentleman silently wonders whether he’d be better off just quietly slipping away.

To an island. Real or figurative. Maybe to a place hiding in plain sight. Somewhere… else. Where the rules are different. Where even ordinary guys can hold things luxuriously in reserve. The upper classes used to keep themselves out of the papers. There’s an aspirational notion. Drop out, turn off, and tune in. You lost the world: it’s okay. It’s better “here.” Never tweet. Never brand. Never care. Gentle, man.

It would make a nice, clean finish to say this is what terminal Playboy is up against. But these are boom times for Workboy—so much so that all the world’s workboys are “happy” to spend their lives competing full-out to conform to the type.

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