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What Makes Something Enjoyable?

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Art is subjective” is a statement we are all familiar with, and have probably said ourselves at one time or another. But what exactly do we mean by ‘subjective’? If I were to say “SSLP and MMLP are the only good albums Eminem ever made”, I might quickly be hit with a reactive “That’s subjective!!!” (though they’d be wrong). However, if I were to say “Etta James is a better singer than Helen Keller”, I’ll probably receive a very concerned look followed by the words “Yeah… obviously”.

So why do we agree on the so-called “obvious”? Why is it that everyone enjoys music, but not everyone enjoys sport? Why is it that everyone enjoys Michael Jackson, but not everyone enjoys beatboxing? Why is ‘enjoyment’ – if it is so subjective – often times so ultimately predictable?

I believe there is a two-part answer to this question:

  • Half is on the side of the viewer

  • And half is on the side of the viewed

The Skill of Enjoyment

Enjoyment is not as naturally built-in as the ‘like/dislike’ that we have for, say, flavours and sounds. In fact, you can enjoy something without necessarily ‘liking’ it at all. This could be true for performing awful dares, watching an uncomfortable film or documentary, or pushing those gnarly last few reps at the gym.

A lot of enjoyment comes not through feeling, but through intellectualising or some form of thought process that leads to mental resolution, like solving a puzzle. And to do that requires some level of familiarity. By expanding your knowledge on something, you open yourself up to the dissatisfaction of wanting the perfect version of it, but also the satisfaction of finding a version that is as close to perfection as you can fathom. The more you know about something, the more you can think about it, and the more you can think about it, the more tools you have to unpack, explore, and resolve it.

Artistic Paradox

 

Elizabeth Gilbert, author of ‘Eat, Pray, Love’, said in an interview with Tim Ferris that great art has two chief characteristics: it is both surprising and inevitable. An easy example of this is a good joke; at first you are stunned by the unexpected punchline, but then come to realise that said punchline is quite a natural consequence – only YOU failed to see it coming. The same goes for a great plot twist, a great musical drop, or even a great goal. But to see why this combination of characteristics equals enjoyable we’ll have to take a look under the hood and dissect what’s really going on here.

 

In order to conceal an otherwise obvious turn of – or escalation of – events, a work of art must exhibit its own ruleset in a way that makes the viewer underestimate its perimeters. The work of art can then act over and over again within the assumed perimeters of the viewer, solidifying their confidence that they know how much room the work of art has to express itself. Only then can an event happen that is outside of those assumed perimeters, but still adhering to the creator’s ruleset, forcing the viewer to remodel their mental understanding of the artwork and make a new estimation of the perimeters of its ruleset.

 

If I were to draw this process as a representation, it would look something like this:

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The more defined and sensical the ruleset, and the more confidence the author can instil in their viewers’ wrong estimation, the more potential there is to create a satisfying and enjoyable event in the art piece. All forms of art can be broken down in this way.

  • A song might introduce an instrument multiple times on a certain key, with similar rhythms, only accompanying a particular other instrument, making your brain assume that it must do this in order to fit with the rest of the composition, then – when the drop comes – do the complete opposite in a beautiful manner and stun you.

  • A painting may have a man riding a dazzling white stallion towards a creepy castle in a dark and dangerous looking forest. The surprise could be to realise that the horse is unscathed, then the inevitability comes when you realise that the horse is a strong stallion, and it remained unscathed through the forest because of its fierce strength.

  • A story or video game might present the rules of a power system, only to then have a veteran use his abilities in creative new ways that fit within the rules of that system.

Conclusion

The skill of enjoyment plus the artistic paradox. In other words, the viewers tools for unpacking combined with their presumptive expectations being broken by a paradox of obvious/sensical surprise, is what allows us to enjoy things. It has very little to do with inherent likes, stylistic tastes, or any other vague and presumably naturally ingrained concept.

image.png

One can even see how this might play out by watching a game of basketball. Imagine you are an avid fan watching the most intense game of your life, where the losing team needs just one dunk to win it. The ball ends up in their most inexperienced players’ hands. With five seconds on the clock, the ball with the opponent’s weakest player, and his position being on his own side of the court, the other team relax for an early celebration, leaving their hoop undefended. He takes a shot of faith and the ball goes straight through the hoop.

 

Now, had your auntie (who knows nothing about basketball) walked in during the last few seconds of the game, she might’ve simply said “Wow, that was a good shot”. But you… you’re jumping across the room cheering! This excitement is enabled by your understanding for the rules and the situation, the reinforced idea that this player is unlikely to score a hoop from a distance due to his lack of experience and past record of missed shots, and the sensical circumstance of why the opponents left the hoop undefended at that moment.

© 2025 Reason Delafét. All rights reserved.

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