While other programming language communities have their notable figures, there is never as much outright drama surrounding them as we find in the Ruby community. In fact, these Ruby figures are now better known for the drama surrounding them than they are for any software they might've written.
It's really quite strange.
1) Drama: fair point.
2) Personality cult: Not as sure. I've seen more than one newb told "don't waste your time" on the Poignant guide in Ruby forums. why's weakness as a coder is pretty widely recognized. In my opinion maybe over-estimated, esp. relative to people like DHH.
3) To me - I learned Ruby when Rails was in its infancy and the Agile salesmen had barely just hitched their wagon to it - why represents a more innocent period of the Ruby community.
Ruby was really a wonderful place - not-especially talented programmers could explore relatively sophisticated programming language features in a safe sandbox. Everything you'd been doing with Perl or whatever you could do with blocks and lambdas and even call/cc if you didn't mind a huge performance hit (naturally you didn't.)
Maybe it's nostalgia, but I think there was a time when MINSWAN actually meant something. Now, every doofus with a self-rolled YAML parser thinks he's the Steve Jobs Memorial Arbiter of Proper Design over Earth and All Satellites Thereof.
4) Yes, it is strange. But then, this is a Perl- and Smalltalk-based language from Japan.
E.g. take Camping (a micro-web-framework that fit in 4K of code) - it is fascinating as a demonstration of some of the things you can do in little space. It is beautiful as art. It has provided inspiration for a lot of us that finds Rails unnecessarily bloated.
It is also totally unreadable for ordinary developers, weird and quirky to the point that if someone had checked something like Camping into one of our work repos, it'd be a "ha-ha, now seriously where is your actualy code?" moment.
The Ruby community appreciates code as art, and is probably more than others inclined to blur the boundary between it and what we will accept or even embrace in production systems. But _why's stuff is mostly firmly on the art side.
There are exceptions, e.g. Hpricot was a nice first try that demonstrates some of _why's skill in terms of creating pleasing interfaces, and he deserves credit for that even though HPricot itself has been largely superseded by Nokogiri.
Thirty years ago Ruby-style drama would have played out as drunken rant at a post-conference hotel bar, or a snide comment on Usenet, or on an obscure mailing list. Not quite the same.
The Ruby guys didn't have the benefit of age, experience, or a certain amount of professional obscurity.
Once you ascribe cult-like groupthink and behavior to a diverse and disconnected group of people who happen to write code in the same language, "leaders" of the cult will emerge from the noise. If you think DHH is some worshipped leader of Ruby programmers, you should read the GitHub comment threads on some of his changes to Rails.
2. Become semi-famous in said community by publishing a few puzzles and an intro book about programming. Doesn't have to be particularly insightful, mind blowing or even good by common standards as long as it's "quirky" and light hearted.
3. Become a cult symbol by dropping off the internet.
4. Come back after a few years and receive a Second Coming treatment.
5. ???
6. Profit!!!
(Of course I don't think this is an elaborate scheme by this guy and I see nothing wrong in his actions. I am only perplexed and turned off by the drama-seeking mentality of the (supposedly) rational, left-brained individuals that are expected to populate a programming community).
The community is like a boiling pot. Sure, handle it the wrong way and you might get turned off, but there is a lot of energy there.
Drama happens when you have a bunch of opinionated people who care deeply about their craft expressing their opinions.
If you can ignore the drama, i think you'll find the creativity more than makes up for it.