This is part 2 of The Rails Generation Gap series.
When people talk about the early Rails community, they often focus on the code. But for me, what stands out are the characters, the voices, and the quirky ways we learned.
Before coding bootcamps, learning Rails wasn’t as structured as it is today. There weren’t week-by-week curricula, Slack mentors on call, or neat tutorials for every error message. Instead, we relied on a patchwork of pioneers who shared their wisdom in creative, sometimes eccentric ways.
It was messy. It was magical. And it shaped a generation of Rails developers.
RailsCasts: Mentorship at Scale
If you were learning Rails in the late 2000s or early 2010s, chances are you watched Ryan Bates’ RailsCasts. My daughter knew the opening music from RailsCasts and would ask “Are you watching that guy again?”
Every week, Ryan released a short screencast walking through a gem, a pattern, or a tricky concept. They weren’t flashy. They were practical, approachable, and packed with insight. For many of us, RailsCasts was the bootcamp before bootcamps existed.
I still remember pausing a RailsCasts episode every 30 seconds to copy code into my editor, rewinding when I inevitably missed a step. Ryan had this gift for making complex things feel doable. He wasn’t just teaching features—he was teaching how to think in Rails.
To this day, RailsCasts remains a cultural landmark. The catalog stopped updating in 2013, but developers still revisit those episodes like treasured textbooks.
_why the Lucky Stiff: The Poet of Ruby
The Rails community also had its artists. None more famous—or infamous—than _why the lucky stiff.
_why wasn’t about documentation or best practices. He was about joy. His works—like Why’s (Poignant) Guide to Ruby—were whimsical, surreal, and filled with cartoon foxes. It was less a tutorial and more a love letter to programming.
For many newcomers, _why’s writing made Ruby feel human. He reminded us that code wasn’t just logic; it was creativity. His sudden disappearance in 2009 left a hole, but his spirit still lingers in how Rubyists value expressiveness and fun.
I wont go into the details here but chek out these articles to learn more about _why:
Rails for Zombies: Learning Could Be Playful
Not long after, platforms like Code School (before it became Pluralsight) gave us Rails for Zombies, an interactive, gamified way to learn Rails right in the browser.
Instead of dry documentation, you solved challenges to help animated zombies complete tasks. It was playful, experimental, and hinted at what was coming: a world where Rails education could be accessible to anyone, not just those willing to dig through mailing lists and source code.
Check out the Rails Conf 2013 Rails for Zombies talk to see what I mean.
What This Era Felt Like
Taken together, RailsCasts, _why, and Rails for Zombies illustrate the unique vibe of the pre-bootcamp era:
DIY Learning → You pieced things together from blogs, screencasts, and mailing lists.
Personal Mentorship → Help often came from a single person’s voice, not a company’s curriculum.
Culture & Quirk → Learning Rails wasn’t sterile; it was filled with personality, creativity, and play.
It felt like joining a small club where everyone knew each other’s names. But it also meant access was uneven. If you didn’t stumble onto RailsCasts, or if _why’s whimsical style didn’t click with you, your learning curve could be brutal.
What We Carry Forward
Looking back, I think this era left us with two big lessons:
Learning is cultural, not just technical. The Rails community thrived because it had voices like Ryan Bates and _why who made knowledge stick.
Accessibility matters. Rails for Zombies hinted at something powerful—that playful, approachable learning could open doors to more people. Bootcamps would later take this idea to scale.
Closing Thought
The Rails of yesterday was small, quirky, and often hard to penetrate. But it was also a place where creativity, mentorship, and community shone through individual voices.
If you learned Rails through RailsCasts, _why, or Rails for Zombies—what do you remember most? And what do you think today’s newcomers are missing without those touchstones?
