It is easy to see _why as "the crazy ruby guy who wrote some scripts and created all this drama around his persona". Even though _why did indeed write some (very useful) programs, I think this view of him misses the point and probably explains why so many people seem to be puzzled by his newest endeavour.
Yes, he wrote some Ruby code, but the code was his least important contribution.
_why was the first person to actually create art around and about software. Others before him have used software as a tool in their artistic process, but to my knowledge no one has ever taken coding as the subject of a performance art so intricate and beautiful as the character whytheluckystiff. All his scripts, all his writings, even all his quirky animations and songs show a love and passion for coding as a recreational activity that defies our conventional beliefs about software as a craft & industry.
We often hear people in this community talk about elegant code, beautiful code, even code as art. But all these sentiments usually mean art in the form of craftsmanship: We want a shorter way to write the same web app, a more expressive way to create our tests, a more concise DSL for data manipulation. While all of these are worthy goals, they are only a tiny, tiny fraction of what coding really is or at least could be. If something doesn't help us build our MVP faster, it's useless to us. Isn't there more to software than that? Sure, there are people focusing on more esoteric stuff in their free time, writing their own Lisps, exploring different data structures, etc. But all of these activities still follow the same tenets: More efficient is better, smaller is better, better is beautiful. We are in love with perfection and purity, because that is what we (necessarily) strive for in our daily work.
_why was different.
Similar to how the decadent and symbolist movements of the late 19th century popularized "Art for Art's sake", _why devoted his whole opus to "Code for Code's sake". His work as a "freelancer professor" showed how much he cared about children learning programming as an enjoyable activity, not as a way to increase the supply of professional programmers. He also satirized our obsession with exactly this professionalism that tends to creep into our thinking and permeates our culture. In short, he used his character to show us aspects of software that were largely underrepresented or ignored in most mainstream discussions.
Personally, reading the poignant guide was the first time I read a piece of code not to understand the code, but to understand a wonderful story. I still don't know how to program in Ruby, but that doesn't matter. In my opinion the poignant guide never really was about Ruby. It was a wonderfully quirky book that happened to be using Ruby as its language. _why's style is absolutely unique and reflects his approach to coding: It doesn't have to be (what we normally consider) beautiful or clean, but it nevertheless forms a great and intricate experience for the reader.
Similarly, today was the first time that I regretted not owning a printer. To see new pages suddenly arrive in the tray to form a crazy and beautiful story must have been magical. Even using only a virtual printer it was wonderful to read the new parts of the book as they arrived and this experience alone made it worthwhile for me. The content itself deserves more than just this quick HN comment though.
So, if you want to know why so many people seem to enjoy the works of _why, set aside some time and start to dig through his estate of old stuff. Don't try to find something useful, just let the whole strange collection sink in. As is often the case with art, the subjective experience is hard to put into words as it depends so much on your personal context and the context of the artwork. I have definitely done a shoddy job trying to describe what makes _why special for me, I am not even sure it can be adequately put into words. But if you like things that are absurd, sometimes useless, yet strangely beautiful, then take a closer look at this works.
Thank you for everything, _why.
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A friend asked me to post this for him.