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why the lucky stiff

Abstract

For about eight years, the most beloved figure in the Ruby community was a pseudonym. why the lucky stiff (written _why) taught programming through cartoon foxes, wrote a microframework smaller than this article, played art-punk keyboard at programming conferences, and built tools to give children the joy of coding. Then, on August 19, 2009, he deleted everything: Twitter, GitHub, every website, every repository. No explanation. The community’s scramble to restore his work from mirrors and caches became an early, formative lesson in what open source loses when it depends on a single person, and what it can save when it acts together.

Code as Art

_why appeared in the Ruby community in the early 2000s as a writer, cartoonist, musician, and programmer who treated all four as the same activity. Alongside Ruby’s creator Yukihiro Matsumoto and Rails’ creator David Heinemeier Hansson, he became one of the faces of Ruby’s rise, except his face was never public. He gave talks, interviews, and performances (with his band, the Thirsty Cups, at RailsConf 2006) strictly under the pseudonym.

His signature work was _why’s (poignant) Guide to Ruby, published free online from 2004: a programming textbook in the form of a surreal comic novel, narrated between chapters by cartoon foxes demanding “chunky bacon.” The word poignant was the stated ambition; he wanted readers moved to tears by code. It is likely the only language tutorial with a soundtrack.

The software was equally idiosyncratic and equally serious:

  • Try Ruby, an in-browser interactive Ruby prompt with a guided tutorial; the template for virtually every “try X in your browser” language site since.
  • Camping, a complete web microframework in under 4 kilobytes of Ruby, written as a comment on Rails’ growing weight.
  • Shoes, a GUI toolkit for building desktop apps in a few lines of friendly Ruby.
  • Hackety Hack, his final project: a programming environment for children built on Shoes, deliberately reviving the spirit of BASIC: a computer you can program the moment you switch it on.
  • RedCloth, the standard Ruby implementation of the Textile markup language, workhorse infrastructure used by thousands of applications.

The Philosophy

_why argued that programming was losing its amateurs: that “when you don’t create things, you become defined by your tastes rather than ability.” His projects were aimed at the beginner, the child, the artist: people the professionalizing software industry was leaving behind. He called himself a “freelance professor.”

The Infocalypse

Shortly before the end, an anonymous blog post outed _why’s legal identity as Jonathan Gillette, publishing personal details including his address and his wife’s name. Whether this triggered what followed is unconfirmed; he never said.

On August 19, 2009, _why’s Twitter and GitHub accounts and all of his websites went offline within hours. The Poignant Guide, Shoes, Hackety Hack, Try Ruby, years of essays and art, gone. There was no announcement, no farewell, no explanation. The Ruby community initially feared for his life.

Then it organized. Within days, developers reassembled his projects from local clones, mirrors, and caches. Steve Klabnik took over maintenance of Hackety Hack; Shoes was continued by the community (eventually as Shoes 4); the Poignant Guide was restored from archives and remains online. A 2012 Slate investigation confirmed through an intermediary that Gillette was alive and well: “Jonathan is _why, he is fine, and he just wants to be left alone.”

In early 2013 the silence broke once, strangely: his old domain briefly served a final work called CLOSURE, delivered as raw printer spool files, without instructions. Readers had to figure out how to render them. Klabnik compiled the pages into a PDF. The book is a meditation on quitting, privacy, and what creators owe their audiences. Then the domain went dark again.

The Legacy of a Deletion

The disappearance became a case study quoted in every debate about open-source sustainability: critical infrastructure (RedCloth alone was embedded everywhere) had depended on one anonymous volunteer, and it vanished with him overnight. The episode helped normalize practices the ecosystem now takes for granted, forking as preservation, redundant mirrors, and community ownership of important projects rather than single-maintainer control. The same fragility surfaced elsewhere in the ecosystem; see The Rise of Developer Communities and The Open Source Revolution.

His stylistic legacy is just as real: Try Ruby’s descendants are everywhere programming is taught in a browser, and Ruby’s culture of valuing programmer happiness and whimsy (visible throughout Ruby and Rails) bears his permanent imprint.

Dead End: Hackety Hack

Hackety Hack was _why’s bet that the missing rung on the programming ladder was a friendly first environment: BASIC for the 2000s. After 2009 the project survived on community effort for a few years, then stalled.

Why It Faded

Hackety Hack depended on Shoes, a GUI toolkit maintained by volunteers across three operating systems, a brutal maintenance burden for a niche project. Meanwhile the “programming for kids” niche was filled by better-funded efforts: MIT’s Scratch, Code.org, and the Raspberry Pi Foundation. The dream didn’t die; it was realized by institutions instead of an anonymous artist. What was lost was the aesthetic: Hackety Hack treated the child as an artist to be delighted, not a future employee to be trained.

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