Let's start by separating the adjective from the verb. (From two verbs, rather.)

When a work or an experience is entertaining, we're describing a quality. This thing engages us! It keeps our attention. For a work to entertain, it has to offer us some reason to stay interested.

When a person (or an artist or an entertainer) is entertaining, we're describing an intention. My goal is to keep you entertained. If I'm creating something, or offering you an experience, I intend it to entertain you.

And when you, in the audience, are entertaining something—a person or a work or an experience—it means you have chosen to give it your attention. For some reason, be it interest or amusement or politeness, you have chosen to give it your time or energy or effort.

The last of these is the most interesting, because it suggests the wide variety of ways in which it is possible to entertain. Anything that an audience continues to pay attention to can be called entertaining. To split a subtle hair: entertainment isn't what engages us, it's what we choose to engage with. An entertainer might play with things that engage or amuse or interest us; most do! But on a deeper level, an entertainer plays with choice. To entertain is to make us choose.

A work of art or an experience entertains when we choose to give it a try, or choose to continue with it. A person successfully entertains when they prompt us to make that choice. 

Because entertainment can be said to manipulate that choice, you can make the argument that entertainment shares certain properties with addiction.

When a work or an experience is acutely entertaining, we continually choose to focus on it—perhaps over other things. When a person is acutely entertaining, they continually convince us to pay attention to them, regardless or not of whether we "should," or even (on some level) want to. 

It's possible to entertain someone's existence in ways that you resent, to find yourself thinking of them when you wish you weren't, or to find them inescapable in some way. And it's possible, of course, to get so focused on some kind of experience—a piece of media, a digital platform, a physical act, even an unhealthy relationship—that you start to lose control over whether or not you pay it any mind. The choice to disengage might feel increasingly hard to make, or you might forget that you can choose to disengage at all.

First and foremost, I suspect, I am an entertainer. It delights me to entertain. I get bored when I'm not entertaining. (Or I get bored when I'm not entertained, which drives me to entertain others.)

You could even say that it entertains me to entertain: that I find entertaining others more personally entertaining than most other kinds of entertainment. Some entertainers suspect that they do what they do to seek validation of some kind; I'm not sure that that's my motive. For me, it's likelier that entertaining others is one of the easiest ways for me to get entertainment out of them: while I'm delighted when a person is genuinely engaging and interesting, plenty of people aren't. Entertaining them is almost like a way of bridging the gap between us: it helps me stay engaged with them, even as it keeps them engaged with me.

It also entertains me to try and make things entertaining: to develop a craft of entertainment, and to find ways of making the things I make more entertaining in and of themselves. I find entertainment an endlessly entertaining subject. (I promise not to write sentences like that too often.)

Filmmakers sometimes use the word spectacle to refer to any scene or event or quality whose primary purpose is to engage the audience in some way. More artful filmmakers seek to embed the substance of their movies with spectacle: to find the most compelling way to depict something that needs depicting. Less sophisticated ones treat spectacle as a shim of sorts, a wedge to slip in at planned intervals to keep everyone happy. And there are other filmmakers for whom spectacle itself is their primary craft: their goal is to find new ways to delight or astound.

While there's nothing inherently wrong from setting out to entertain, I think there are conversations worth having about the healthiness or even the ethics of entertainment. For one thing, I think that there's a difference between intense entertainment and addictive entertainment. The most addictive experiences are not necessarily the most satisfying ones: often, they're the ones that intentionally craft dissatisfaction, offering us just enough to keep us seeking satisfaction, but never enough to satiate. That's not the same as things that seek to intensely delight or intrigue or grip us, in ways that help us shift our focus once we're through with them.

Gambling is a prototypical example of addictive entertainment that rarely satiates: even its most intense peaks leave gamblers craving more. Social media, which intentionally fosters listlessness and tries not to offer "completion," is another obvious example. And a certain kind of gameplay qualifies too: the kind in which every action is easy to complete in and of itself, but where there are endless actions to be undertaken, a piecemeal striving towards a vast and nebulous goal.

It's possible to study the craft behind this kind of entertainment, and to appreciate it when it's done well. But I think we should differentiate between this entertainment and the sort that wants to offer us a vivid, finite experience: the kind of entertainment, in other words, that has some sense of when it wants to end. That sort of entertainment has an objective, even when the objective is to entertain. Entertainment is the substance. And that word, "substance," feels useful here: we can evaluate whether a work or an experience is substantial, and we can include works of "pure" entertainment if we feel they are substantially entertaining.

(Conversely, a creative work intending to have substance to it doesn't inherently make it substantial. Not all unentertaining things are innately "worth" us entertaining them. Some candy tastes like shit; some vegetables are delicious.)

Relatedly, I think we can differentiate between people who set out to create entertaining work and people who set out to continually entertain.

Someone who crafts entertainment is creating that finite, specific experience with a sense of its own ending. Someone who purely seeks to entertain is hoping to grab our attention as much as possible, as often as possible, and by any means necessary.

The latter type of person, I would argue, is inherently more insubstantial than the former—or at the very least they are at risk of being more insubstantial. The urge to entertain, the urge to be entertaining, has a way of collapsing other values or motives. In the same way that our pursuit of entertainment can lead to us discarding substance, the pursuit to entertain can get in the way of other creative pursuits.

We don't have to get puritanical about this. It can be fun to entertain. Not everything has to be a creative work. My all-time favorite description of Twitter is that, at its best, it was ambient: it allowed for socializing in more relaxed, less deliberate ways, which is what made it such an entertaining platform. And the act of entertaining can be ambient too, suffusing friendships and social spaces in ways that make them fun to take part in.

But when that desire to entertain gets intense enough—when it becomes an obligation or an addiction—the result can be insidious. Cancerous, even: the desire to make people choose us can drown out both anything else we might have to offer and anything else our audience might fill their lives with. Addiction to entertainment runs both ways: it's as noxious for the entertainer as it is for the entertained.

Andy Kaufman is revered as an entertainer. He was more than a comedian. He was a performance artist.

Taken literally, that term means: he called our attention to him in strange and unexpected ways. He created wondrous spectacle out of his own life. The events of his life, in a sense, were his creative work.

Kaufman is sometimes seen as a visionary, in the way that his work seemed to anticipate a world in which people are drawn to call as much attention to themselves as possible, and by whatever means necessary. In some ways, people think that his work serves as a forebear for reality TV, the Kardashians, Paris Hilton, and maybe Kanye West's perpetual attempts to provoke our attention.

You can draw a line from Kaufman to Shia LaBeouf, who, after he was caught plagiarizing another writer's work, responded with a series of escalatingly weird attempts to call attention to his own status as a celebrity. And you can draw a line from LaBeouf to Logan Paul's shooting video of a suicide victim in a notorious forest in Japan. (In 2026, of course, no figure looms larger here than Donald Trump, who has the power to make himself very difficult not to pay attention to.)

I'm bringing up Kaufman because I do think his work is different from anybody else's mentioned here. There was a substance and a craft to what he did that goes beyond "grab attention." He entertained in ways that go beyond hijacking our choice of who and what to pay attention to. Yes, he blurred the line between his person and his work, but he did that by making a substantial work out of his persona. The difference between Kaufman and everybody else mentioned here is that, every time Kaufman called attention to himself, he found intriguing new ways to entertain. In a sense, his work was similar to Marcel Duchamp's: the innovation itself, the redefining of what entertainment could be, was itself the entertainment. 

The mere act of trying to grab attention is not inherently substantial. I'd argue that that's usually true even when it's effective. And I'd further argue that, while devising new techniques for grabbing our attention might be considered a kind of substance, it's rarely that substantial in and of itself, unless it's paired with some other dimension or quality that makes it worth our while.

Hopefully I'm drawing a somewhat lucid line, here, between the kinds of entertainment that I think are substantial and the kinds of entertainment that aren't. The act of entertaining can be inherently substantial, given innovation and imagination and verve and style and craftsmanship, but these are the qualities that give entertainment its substance. Similarly, someone who seeks to actively and ongoingly entertain us can do so in ways that offer us something substantial, but simply convincing us to entertain their existence isn't enough.

The question that interests me here is: how do we differentiate between meaningfully entertaining works and meaninglessly entertaining ones? More importantly, how do we differentiate between the kind of entertainer whose ongoing success is somehow meaningful and the kind of entertainer whose success is instead proof of their meaninglessness?

In an age of information overload, discovery itself can be incredibly difficult; our attention is an incredibly precious, and often-squandered, resource. What we choose to entertain, and who convinces us to entertain them, has higher stakes than we admit. When we can't be guided by institutions or authority or expertise—and all of those have been seriously eroded—our attention, and to some extent our perception of reality, is on sale to the highest bidder. 

It's important for us to ask how to evaluate people who are making bids for our attention, and to figure out who we should and shouldn't entertain. And it's important for people who want to be entertainers to ask whether they're bidding for our attention in ways that matter—and for people who want to say or do meaningful things to work out how they can persuade us to entertain their ideas and their work and them, without sacrificing what they wanted to give us in the first place.

Any culture that demands we constantly entertain people if we want them to pay attention to us is inherently cancerous. Any content platform that pushes engagement towards its most active "creators" is de facto penalizing people who choose to be any less active in their attempts to keep us hooked.

We can and should call these platforms, and our culture at large, toxic and unhealthy. But in the meantime, we are part of this culture, and it's unlikely that we'll see a mass exodus from it any time soon. So whether or not we think it's healthy, we're forced to play by its rules—which means that it'll push us to propagate these toxic, unhealthy behaviors ourselves.

So how do we do effective work within these platforms without perpetuating their worst tendencies? How do we entertain without turning the act of entertaining meaningless?

One approach is the one that effective politicians take: stay on message. Whatever you're here to say, keep on saying it—and keep finding new ways to keep it entertaining.

Another approach: find ways to keep yourself on people's radars without being too attention-grabby—keep yourself ambiently around, ambiently entertaining—and then call attention to yourself when you finally have something meaningful to share.

A third approach: find some way to turn your new work into an event, and heighten the buzz around it by keeping quiet until you're ready—though this only works if you can guarantee that people will remember you enough to talk about you, when it's finally time.

These aren't the only possible approaches. There are plenty of others.

When you do have something worth sharing, is its substance alone enough? Will that be enough to get your audience to entertain it? Do you need to make it more entertaining, somehow? Do you need to find better ways of provoking or persuading people into giving it attention?

The more you resist that urge to constantly entertain, the more you try not to grab people's attention, the more you'll have to do when you genuinely want them to pay attention to you. Conversely, the more you do ask for people's attention, the harder it will get to direct their attention to one specific thing of yours, when that's the thing you want their eyes on.

Personally, while I enjoy both entertaining others and the craft of entertaining, I try not to put too much effort into specifically trying to entertain, up until I think I've done work worth noticing.

I'm far more interested in the challenge of finding entertaining ways to explore the things I find substantial. First and foremost, I want to articulate something of substance; secondarily, I want to turn that articulation entertaining, somehow. I want to see if I can convince people to pay it any mind. I want to see what does persuade people and what doesn't, what successfully entertains and what loses interest.

At the same time, I like to entertain myself, and I like to share the things that entertain me, and I like to see which of those things entertain other people too. The objective isn't to get better at entertaining other people in the short term... but I do pay attention to what happens.

When it comes to producing more serious work—which I haven't really done before now, but years and years of preparation are at last about to bear fruit—I think there's something to be learned from Andy Kaufman. We have no choice but to exist in this culture that demands we call attention to ourselves... but there are ways of grabbing attention that become meaningful, substantial experiences in their own right. Every attempt to create a meaningful event is an act of resistance against the platforms that try to push us towards meaninglessness. We should ask ourselves what it might mean to push back, and when we ought to try, and what we might do that's worth the effort.

Lastly, I think the most important thing we can try and do is provide new platforms, to push back against the shitty old ones. Content isn't enough—platforms are what matter.

Our goal should be to create as big and as meaningful a series of platforms as possible. Publications like Defector or Flaming Hydra. Streaming services like Nebula or Dropout or even Taskmaster. Ideally, new social media platforms: ones that can genuinely replace our dependency on the present toxic landscape without perpetuating their toxicity, though that's clearly a challenging ask. 

But we should also seek new and novel opportunities to create platforms. We should try and imagine brand-new kinds of platform, new kinds of engagement and discovery, new kinds of entertainment. We should imagine ways to slip these platforms, Kaufman-style, into people's lives, in unexpected and wondrous ways. We should try and aggressively seek out new ways to replace what is with what could be.

The titans of our present entertainment landscape—the TikToks and Instagrams and Twitters, the Polymarkets and Kalshis and DraftKings, and, yes, the Animal Crossings and Stardew Valleys and Calls of Duty—succeed by persuading us to empty our lives of everything but them. The emptier we let them make us, the more room we have for them to fill us—and the harder it becomes to imagine replacing them enough to finally escape them.

If we want the next replacement, the next escape, to be something better than just the next flavor of empty, insubstantial bullshit, we need to create a lot of replacements. A lot of escapes. A lot of new kinds of entertainment. 

We can't just seek out new ways to manufacture emptiness, and we can't be content to manufacture the kinds of entertainment that work within those empty spaces. We have to invent new ways to fill lives. Which means we have to discover new ways to entertain.

I believe that this pursuit of newer, better ways to entertain is a genuinely existential challenge. And it is a response to an ongoing existential threat.

We can't deny the importance of entertainment, or fantasize about a world in which everybody simultaneously devotes their attention to important and meaningful things. This bullshit all exists because we like it. It's a virus that has successfully found a host. Instead of rejecting that, we have to make peace with it. This desire to entertain and be entertained is a fundamental part of who we are. Whatever comes next has to take that into account.

But we also can't be complacent. The present moment calls for fiery resistance. We need to push back against entertainment that reinforces the status quo, entertainment that offers us nothing, entertainment that feeds parasitically on the kinds of digital landscape that have foisted social and mental and emotional health crises upon us.

We have to resist our own tendencies to go with the flow, and to conform ourselves and our actions to suit what these platforms want us to become. We have to find ways of prying ourselves free. And we do that by pursuing better ways of entertaining, and better ways of keeping ourselves entertained. We need to create alternatives for people to jump to. We need to give each other motivation to escape.

In his masterpiece Histoire(s) du cinéma, Jean-Luc Godard makes the incendiary claim that Alfred Hitchcock, more than even Adolf Hitler, managed to conquer the twentieth century and the whole world.

To Godard—an artist whose entire brilliant career was about the simultaneous pursuit of substance and entertainment—Hitchcock was the ultimate manufacturer of style. He didn't just create entertainment: he created icons. He created a language, not just of images or dialogue but of emotions. He found a way to translate substance into entertainment. (Or perhaps not to translate, even, but to transubstantiate: to turn personal reality into something genuinely divine.)

Godard was not claiming that Hitchcock was any sort of politician, or that his films had any kind of moral value. His claim was that Hitchcock cracked the code, so to speak, of what it means to intentionally create new culture: to create something that's not merely functional, not merely engaging, but a synthesis of the two. To transform the mere text, and the mere entertainment, into something that genuinely matters. To create something that we engage with, something that we pay attention to, and something that ultimately lingers with us, transforms us, offers us new vocabulary, new ideas, new ways of engaging with the world.

While you could argue that things like emoji or memes give us new ways to communicate, I'm not sure that they fulfill the emotional dimension that Godard finds in Hitchcock, and considers so essential to style. To me, the far more relevant points of comparison would be things like... the original iPhone home button. The social media feed. The notification tray. The dating-app swipe. Doomscrolling. The interfaces and metaphors that define our narrative of technology, and of what it's for, and of what its relationship is to us.

These are our ultimate forms of entertainment: the things that literally define how we choose to engage, and how we're allowed to choose. Our entertainment isn't YouTube videos or songs on Spotify or Reddit posts or TikToks: it's YouTube's recommended videos, Spotify's algorithmic playlists, Reddit's r/popular page, TikTok's continual evolution of what to show you when you swipe.

This is as close as our era comes to what Godard found in Hitchcock. This is the style of our generation. Individual emojis matter less than the fact that devices allow us to choose emoji. Individual memes matter less than the cross-site systems that offer easy access to posting memes. 

Do we like that style? Do we like this world we live in? When we strip away all the content these engines drive us towards and focus on the engines themselves, are we satisfied with this? If not... what are we going to do about it? What are we going to replace all this with? How do we replace the literal symbols and icons of our modern day with newer, better ones? How do we go about creating icons of this nature at all?

This, to me, is the serious work of the modern entertainer. The platform matters as much as the content. The interface is as iconic as the text or imagery or video. 

It matters to me because it's important. But it also matters to me because it's interesting and weird and fun. This is way, way more entertaining, to me, than questions of how to write a popular Substack. Why bother with the tedious generic shit when we could be focusing on this instead?

Defector, which I mentioned earlier, pioneered a radical approach to worker-owned publications, but also advocates a vision of what blogs should be by people who truly believe in blogging as a medium. On the one hand, they reflect that through their editorial choices, which are consistently surprising and entertaining: no web site produces a spread of headlines that's as consistently enjoyable to scroll through as Defector does. On the other hand, the very design of Defector serves as a forceful argument for what makes a good blog good: the way it lays out headlines and categories, the way it highlights certain topics and themes at different times, the way it lets you navigate it as a reader, are all intentional and effective choices that, among other things, offer up a vision of what reading content online could be.

A writer like Jon Bois, meanwhile, what explorations of platform and style can look like for a storyteller. 17776 is creates wholly unique digital realm: every choice it makes, from how dialogue is laid out on-screen to how images intersect with text, affects the experience of reading and watching it. (For pithier examples of narrative interplaying with medium, look to old SomethingAwful series like Monstergeddon or Barkwire, whose stories are wholly interlocked with the "sites" they're told on, or Dustin Couch's social media-based horror stories—but Bois is doing something more profound, by inventing a bespoke new medium for the story he's trying to tell.)

More obvious examples of style can be found in game design—Breath of the Wild's tremendously thoughtful user interface feels as iconic as many staples of social media, but even more relevant is how a game like Minecraft gets transformed into a creative platform in and of itself, whether it's Ish's phenomenal thousand-player civilizations or something as doofy as Parkour Civilization. There's nothing stopping the games we play from serving as social or cultural platforms, just as there's nothing stopping our social platforms from functioning as games; the separation of categories is arbitrary and illusory, maintained by custom and tradition more than anything.

None of these are complete examples in and of themselves. I'm not sure that any of these really deserve the accolades that Godard gave Hitchcock. (If anyone is the Hitchcock of the modern era, it's likely Steve Jobs, for better or for worse.) But these all point to potential new approaches to entertainment—and they all hint at visions of how we might replace the world we're in now with what might come next.