I think his primary appeal is that, in a world that tends mostly towards people like yourself, who view programming as science (or engineering), he unapologetic

I think his primary appeal is that, in a world that tends mostly towards people like yourself, who view programming as science (or engineering), he unapologetically took the opposing view. Your perspective is commonly shared; his perspective was undeniably more singular. One can admire that perspective, learn from it, and be inspired by his passion, without necessarily taking the same approach in your own code. I don't write code much like the way _why wrote code, but I admire what he did and what he stood for nonetheless. _why was drawn to Ruby because of its own artfulness, and playfulness; you would be hard-pressed to come at programming from the same perspective in Python, not because Python isn't a nice language (it is) but because the diktat "there is only one way to do it" necessarily discourages experimental styles of coding, though not of API or visual design. If your medium is code, then it helps to work with a malleable programming language, and Ruby is nothing if not that. Scheme is malleable, but I'd not call it playful. Perl comes closer, but most languages, which are are written by Serious People with Important Goals, do not. Anything that inspires people to stretch their skills and try new ideas out helps grow teams and developers, though preferably not when working with production code.