The paradox of Trump is that he’s an utterly ridiculous buffoon, yet we have to take him seriously. His entire presidency is a massive practical joke perpetrated by him at everyone else’s expense, and it’s a profoundly unfunny one. He’s easy to make jokes about, but that’s precisely why we shouldn’t be joking about him. (A good rule of thumb is that, if anything is too easy to accomplish, it’s probably not what the situation or the moment really calls for).

What’s called for in today’s America is to confront, and first and foremost to understand, what it is about our damaged society that made it possible for such a malign and buffoonish lout to win a presidential election, and what still makes it possible for him to wreak his will upon us.

A starting point toward understanding is the work of the late Neil Postman, a professor who founded a trailblazing graduate program in “media ecology” at New York University and author of several seminal books of incisive cultural criticism. A central statement of what Postman was all about was his assertion that “new technology can never substitute for human values.” That’s a counterintuitive claim to make here in America, where we’ve long been addicted to technology, the newer the better. Indeed, the damagingly central role of technology in American society is the subject of his aptly titled book Technopoly, published in 1992 and never more relevant than now, a quarter-century later.

But the book of Postman’s that is most helpful to us in understanding Trump is Amusing Ourselves to Death (1985), about Americans’ addiction to television and entertainment. I read that book in 2007, and already then, two decades after its publication and a decade ago, the book’s specific references were quaintly out of date. But its message is durably prophetic, partly precisely because of the very quaintness of its dated particulars. The more things change in America, the more they stay the same.

So we amused ourselves to death, until one fine day in November 2016, we woke up to find that Donald Trump had been elected our country’s president. That makes a very long story very short, but it drives home the point that we inflicted him on ourselves, and that it has everything to do with Americans’ obsession with popular culture. An overlapping obsession is our obsession with media – because, of course, popular culture exists almost entirely in and through media. I realise these are not original thoughts, but they’re worth emphasising because American society, per se, really only exists virtually, via our media. This is true partly because of our obsessions (with media itself, with popular culture, with technology), and partly because of the country’s geographic vastness. But the ominous punch line is that America’s virtual existence is closely tied to some important things that themselves exist only virtually, only because we choose to cherish them: abstract things like freedom and democracy.

The recent stories of two female comedians illustrate some of these points. One is the notorious Roseanne Barr, whose popular rebooted sitcom was abruptly cancelled by the ABC network in late May because she tweeted comparing an African American former Obama aide to an ape (throwing in an insinuation about the Muslim Brotherhood for good measure). You’ve probably already read all about that. If not, it’s on the Internet. Roseanne herself is a very Trump-like case study of an American ego that kept expanding until it exploded from sea to shining sea. If her career is now finished, good riddance. But the fact that Roseanne’s erstwhile sitcom was called simply Roseanne shows what we’re up against in terms of Americans’ self-inflicted, and increasing, difficulty in distinguishing reality from what’s on TV or on the Internet. Is Roseanne an actress (Roseanne Barr), a television character (Roseanne Conner), or both? Is she an icon of the now much-vaunted white working class, an unregenerate bigot, or both? Should people like her – people who insist on spewing racist and Islamophobic venom – be coddled, or shunned? Of course they should be shunned. But today’s America is such that simply to say that is to take a bold and even potentially dangerous political stand. If Trump can get away with it, why can’t Roseanne?

A much more serious person is the younger comedian Michelle Wolf, whom I wrote about here a few weeks ago, after her wonderfully brave and unsparing performance at the annual White House Correspondents Dinner. “Trump jokes bore me,” she told journalist Decca Aitkenhead in a remarkable recent interview in The Guardian. “I think the problem is that we all keep confusing humor with facts, or with just pointing things out. People will say, Trump tweeted this, and then he tweeted this – it’s hypocritical! And people will be like, That’s hilarious! I’m like, That’s not hilarious, it’s just a pointing out of two things. There still needs to be a punchline. There still needs to be some sort of twist, or something. I always think of comedy as: it’s not what you want to hear, it’s what you didn’t know you wanted to hear. You should be surprised by what people say, and hopefully delighted, but it shouldn’t be the thing that you’d already thought of. Yet there’s this whole section of political comedy that’s just saying the thing that we want to hear, rather than pushing our brains.”

Wolf also drew an important line between media – specifically the bane that is social media – and real life. “What I like about stand-up,” she said, “is that you tell a joke, and people laugh or they don’t. On Twitter it’s like, you tell a joke, and people try to either correct your joke or complain about it. You know, we’re all spending way too much time on social media, and I thought, ‘This isn’t good for my brain, I’m just going to work on the jokes I’m going to tell in front of people.”