October 5, 2026 ·AI Assisted

Whimsy Is Dead

What happened to the internet? Growing up, the internet was a place filled with whimsy and wonder. It was a place where you could find (almost) anything you wanted, and it was all free. You could spend hours on end exploring the depths of the internet, and it was all there for you to discover. Builders of the Internet Past were making things not just for extracting wealth from their fellow netizens, but for the sheer joy of creating something new and interesting.

Let's explore the history.

The Early Days

The internet was born out of a need for resilient communication during the Cold War. In 1969, the US Department of Defense created ARPANET, the first network to use packet-switching technology. This allowed messages to be broken into smaller pieces and sent through multiple routes, making the network more resistant to attacks or failures. The early internet wasn't designed for commerce or social media. It was built by researchers and academics who wanted to share information and collaborate across long distances.

Universities and research institutions were the first nodes on this network, connecting computers that were rooms apart to computers that were states apart. This academic foundation meant the early internet was focused on openness, collaboration, and the free exchange of ideas, values that would shape its culture for the next few decades.

The 1990s

The 1990s were a time of great change for the internet. The rise of the web browser, and the popularity of the internet as a platform for businesses and personal websites, led to a whole new wave of innovation and creativity. The web browser was a key factor in the growth of the internet. It allowed regular people to access the internet from nearly any computer, and businesses to create websites and sell products and services online.

This was also when HTML (HyperText Markup Language) was created by Tim Berners-Lee while working at CERN in 1989-1990. HTML gave people a standardized way to create and link web pages together, forming the World Wide Web as we know it. The first publicly available description of HTML was released by Berners-Lee in 1991, and it included just 18 elements. This simple but powerful language meant that anyone could create their own webpage. You didn't need to be a computer scientist or professional programmer. Armed with just a text editor and some basic HTML knowledge, people could carve out their own little corner of cyberspace.

<h1>My Home Page</h1>
<p>Hello! Welcome to my
little corner of the web.</p>
<ul>
  <li>Things I like</li>
  <li><a href="links.html">
    Cool links</a></li>
</ul>

The early versions of HTML were beautifully simple. You could create headings, paragraphs, lists, and links - the basic building blocks that would shape the entire web. This simplicity was intentional. Berners-Lee wanted the web to be accessible to everyone, not just technical experts. The result was an explosion of personal websites, each reflecting their creator's interests and personality. From fan sites dedicated to favorite TV shows to personal blogs about daily life, the web became a canvas for individual expression.

My Start in Web Development

I was part of that early cohort of enthusiast web developers and I remember the excitement of capturing my own little slice of the internet. One summer, I broke my wrist and was forced to sit inside instead of playing outside. I fell into the world of web development and I was hooked. I spent hours on end learning HTML, CSS, and JavaScript. I was creating my own websites and I was sharing them with my friends. Surprisingly, it's still up and running today. (Sorry in advance for the adverts.)

The Mid-90s

If the early 90s gave us the tools, the mid-90s gave us the neighbourhoods. GeoCities launched in 1994 and organized its free homepages into themed "neighborhoods", like Area51 for sci-fi, Hollywood for film, SiliconValley for tech. Angelfire and Tripod followed shortly after. For the first time, anyone with a dial-up connection could claim an address on the web without paying a cent or knowing what a server was.

What people built with that freedom was gloriously unhinged. Tiled starfield backgrounds. Spinning stars. Flaming horizontal rules. "Under Construction" banners on pages that would never be finished. Hit counters proudly displaying that you were visitor number 000427. MIDI files that started playing the second the page loaded, at full volume, with no way to stop them. Guestbooks where strangers left kind notes. Webrings that stitched together dozens of sites about the same obscure hobby, so you could click "next" and fall down a rabbit hole someone else had dug for you.

None of it was optimized. None of it was trying to convert you. Most of it was objectively bad design, and that was the point. It was personal. Every page was a fingerprint.

The browsers were catching up too. Netscape Navigator shipped in 1994, and in 1995 Brendan Eich wrote the first version of JavaScript in about ten days. Suddenly pages could react. Cursor trails, scrolling status bar text, and alert boxes that greeted you by name. And then there was "View Source", the greatest teacher the web has ever had. If you saw something cool, you could right-click, see exactly how it was made, copy it, and make it your own. The entire web was an open textbook.

The 2000s

Then the money arrived, and briefly, it left. The dot-com crash in 2000 wiped out a ton of companies that had confused having a website with having a business. But the people who were building for fun didn't really notice. They kept going.

The early 2000s were, in a lot of ways, the peak of internet whimsy. Flash turned the web into an arcade - Newgrounds, Miniclip, Homestar Runner, and thousands of weird little games and animations made by teenagers in their bedrooms. Wikipedia launched in 2001 on the radical idea that strangers would write an encyclopedia together for free, and they did. Blogs exploded. Forums for every niche imaginable flourished, each with its own inside jokes, custom emoji, and signature images.

And then there was MySpace. Launched in 2003, MySpace let you paste raw HTML and CSS directly into your profile. The results were often unreadable. Glitter text on a background of your favourite band, with an autoplaying song and a Top 8 that could end friendships. But a whole generation learned how to code by trying to make their MySpace look cooler than their friends'. It was GeoCities energy with a social graph.

"Web 2.0" became the buzzword of the decade, describing a web where users created the content instead of just consuming it. That sounded like a continuation of everything good about the 90s. In hindsight, it was the turning point. If users create the content, then whoever owns the platform owns the content, the audience, and the attention.

Facebook made that trade obvious. Where MySpace let you make a mess, Facebook gave everyone the same clean blue-and-white template. It was easier to use, easier to read, and much easier to sell ads against. Users loved it. The weirdness was quietly sanded off, and we barely noticed because our friends were all there.

In 2009, Yahoo shut down GeoCities. Millions of personal pages, a decade of the internet's folk art, were deleted. If it weren't for volunteer archivists who scrambled to save what they could, most of it would be gone forever.

The 2010s

The iPhone launched in 2007, and by the 2010s the internet had moved into our pockets. That changed everything about how it was built. Screens got smaller, attention got shorter, and the open web started giving way to apps. Apps were walled gardens with a single front door, owned by a single company.

In 2010, Steve Jobs published "Thoughts on Flash", and the beginning of the end for the web's arcade was set in motion. Flash had real problems, but its slow death took a huge chunk of creative culture with it when Adobe finally pulled the plug at the end of 2020.

Meanwhile, the chronological feed died too. Facebook, Instagram, and Twitter all moved to algorithmic timelines, deciding for you what was worth seeing based on what would keep you scrolling. The goal was no longer to help you find things; it was to keep you from leaving. Engagement became the only metric that mattered, and everything on the internet started bending itself towards it.

Websites started to look the same, too. Frameworks like Bootstrap made it trivial to build a decent-looking site, which was genuinely great, but it also meant everyone's site had the same hero banner, the same three-column feature grid, and the same hamburger menu. Growth teams A/B tested every button colour. Landing pages were engineered to convert. Design became a science of persuasion instead of an act of expression.

Nobody set out to kill the whimsy.
It just didn't test well.

Where Did It Go?

In my last essay, I wrote about how "The House Always Wins" has become the operating principle for the gambling industry, and that the same idea applies to the internet economy as a whole. This is that essay, or at least the start of it.

The internet of today is very good at extracting. It extracts our attention through infinite feeds. It extracts our data to sell us things we didn't know we wanted. It extracts our creativity, too. We post into platforms we don't own, under rules we don't set, for algorithms that can bury us overnight. The platforms are the House, and the House always wins.

Search for anything now and you'll wade through SEO-optimized listicles, affiliate links, and pop-ups asking for your email before you've read a sentence. More and more, you'll also wade through content that wasn't written by a person at all, generated at a scale no human could match, purely to capture a click. The weird, hand-made corners of the web are still out there, but they're buried under a mountain of stuff built to be found rather than built to be loved.

That's what I mean when I say whimsy is dead. Not that nobody is making fun, strange things anymore. They are. It's that the internet is no longer built for those things to be discovered. The incentives point the other way.

Long Live Whimsy

Here's the thing though: I don't think this is permanent, and I'm not interested in writing a eulogy.

There's a quiet movement of people rebuilding the old web on purpose. Neocities, launched in 2013, is a spiritual successor to GeoCities, and it's full of handmade sites with blinking GIFs and webrings, made by people who weren't even alive when the originals went offline. Personal blogs and newsletters are making a comeback. RSS never actually died. The "small web" and "indie web" communities are full of people who want to own their corner of the internet again.

And it has never been easier to build. When I was stuck inside with a broken wrist, I had to learn everything one tag at a time. Today, the tools are so good that the barrier between having an idea and putting it on the internet is almost gone. The same technology that's flooding the web with slop can also put the ability to build something delightful into the hands of anyone who wants to. The question isn't whether we can make the internet weird again. It's whether we want to.

I don't think regulation is the answer. I think it's builders. People who make things for the joy of it, who own their own little slice of the web, and who care more about delighting someone than about converting them. That's how the internet started, and I think that's how it gets better.

So go make something. Make a personal website with a ridiculous background. Make a tiny game. Make a guestbook and ask your friends to sign it. Make something that has no business model at all.

My Angelfire site is still out there, ads and all, a little time capsule from a kid with a broken wrist who thought the internet was magic. I'd like to think it still can be.