Let me modify the OP's comment, Jacques: _why was one of the first people to create art around and about our modern software community.
There are a variety of cultures surrounding coding which, while somewhat diverse, still feel like somewhat of an echo chamber. You have the coding-for-startups culture, for one, and then you have people who are very invested in coding efficiency for the sake of coding efficiency. Both of these are healthy things to have exist, but they lead to a few very specific personality types dominating the landscape, and the result is that programming can seem very forbidding to people who don't match those sorts of identity. Heck, it can be forbidding to people who do match them. And you have little clusters of hobbyists here and there, but those clusters are easily overlooked by people who aren't searching for them.
The message I felt _why delivered with his work more than anything was that programming is fundamentally about more than code, or even about building. He tried to capture the emotions behind programming, the joy of learning to speak logic-driven languages, the humanity behind the hobby. And that humanity wasn't just bubbling whimsy and childlike wonder, though certainly _why dabbled in his fair share of that. There was a whole lot of insecurity, fear, worry that he might be throwing his life away on something impermanent and... not frivolous, because frivolity suggests a joy... neurotic, perhaps. Something that ultimately was consuming his time for no good purpose other than that he was locked into a pattern and couldn't see beyond it.
As somebody who's not a programmer, not even really a designer, that message struck me hard and deep, and _why sure seemed like the only person getting it out there in any big way – at least sometimes. In every other creative community I'm tangentially a part of, that dark pit of uncertainty tends to play a big role, not only in shaping the culture, but in shaping the creative direction of the medium. Musicians ask themselves whether the music they're playing is pointless, or whether the way they're making music is somehow harmful or runs contrary to the feelings they're trying to evoke. The result is that music changes. Directors ask all sorts of questions about how film should be made, how much a shot should be composed or "designed". Actors have a bevy of debates about artifice or insincerity in their roles. And writers... well, writers are about as fucked-up a category of people as they come, to the extent that the nicest and friendliest writers will cheerfully talk about how their entire life's work is probably futile and pointless.
_why wasn't a very good programmer, from what I hear, but his messiness was anathema to the kinds of cultures I usually associate with programming. He played games, and worried out loud, and made it seem like the secret to everything he did was that combination of caring/not caring that he was constantly oscillating between. The first thing that struck me about this print spool was how much it felt like a maturation of his message: not quite as whimsical, but silly in more nuanced ways, and more on-target serious about things he felt bothered by without feeling as impulsive as some of the things he wrote earlier. I love his Guide to Ruby, but there's certainly a bit of a mood-swinginess to it that this lacks.
First artist to work with software, or to comment on software? Hell no. But he felt, at times, like he was the only artist within this makeshift community that was really talking about how it felt, how it worked, what was so frustrating or nerve-wracking about it. That's why, I think, so many people treat _why like he was something special. It's probably also why so many other people don't get his appeal at all: for them, the culture that exists is exactly the one they want, and they find it irritating (if nothing else) that this "jester" was prancing about talking about non-relevant things.
