Let’s be honest: the early web had a charm that the modern, bloated internet has completely lost. Back in the nineties, when dial-up modems whistled their handshake protocol and netiquette was still a novel concept, we shared humour differently. We didn’t have algorithmically optimized feeds or infinite scrolls. We had email forwarding. If a joke was funny, it got copied, pasted, and forwarded through POP mail clients to everyone on your contact list.

Back in the 90’s I ran Joke A Whenever, a joke site I couldn’t quite commit to publish on a set interval, in part jest and mimic of all the Joke a Day/Week/Month mailing lists that were all the rage. In addition to the website was a daily mailing list hand sent to ~4500 emails at its peak on a typically daily basis. The advertising slots in that mailing paid for my first laptop.

I recently dug up that archived giant, dusty Eudora mailbox file containing thousands of these plaintext relics that had sat undisturbed since the nineties. It was a time capsule of internet culture, but it was also a disorganized, unformatted mess in a now obsolete file structure. I decided it was time to build a pipeline to clean them up, bring the nineties web back to life, and host them statically. It was also a great time to leverage the latest tech to solve an old problem.

The biggest challenge wasn’t storage or bandwidth; it was the plumbing. Raw email archives from thirty years ago are messy. They are littered with nested quote characters, broken mime-types, encoding anomalies, and duplication. Beyond the formatting nightmares, humour dates itself. Some of these jokes were gems, some were terrible puns, and others contained references that simply do not translate to today’s audience. Hand-sorting and formatting six thousand jokes would take months of tedious labor. To make this project viable, I needed a translation layer that could automate the heavy lifting while preserving the core spirit of the jokes.

To tackle the ingestion, I built a custom parser in Python to slice through the old Eudora mailbox structure and extract the raw plaintext setups and punchlines. Once the raw text was normalized, I wired it into the Google Gemini API. I constructed a strict batching prompt that instructed the AI to act as an editor. The AI was tasked with correcting punctuation, fixing typos, assigning tags, categorizing the content, and flag-marking jokes for family-friendliness. The goal was to polish the jokes without erasing their classic humor, making sure the final output stayed clean and appropriate for all ages.

But as anyone who works with hardware or software knows, you never just push code to production without checking the solder joints. I couldn’t trust the AI blindly to make editorial decisions. To maintain human-in-the-loop control, I spun up a local Flask administration portal. This dashboard gave me a rapid-review interface with custom keyboard navigation. I could click through the polished jokes one by one, instantly tweak AI-assigned categories, rewrite setups on the fly, and delete the ones that didn’t make the cut. The dashboard automatically regenerated the files locally, ensuring I kept full quality control over the final product.

For the presentation, I wanted the speed and simplicity of the early web, but built with modern reliability. Instead of running a heavy dynamic database or wrestling with a vulnerable LAMP stack, I built a static site generator using Jinja2 templates. The generator takes the validated database, compiles all six thousand pages, builds the category pages, and outputs a lightweight, lightning-fast static directory. The final site is deployed directly to Cloudflare Pages at JokeaWhenever.com for all to enjoy.

The result is a blazing-fast, responsive tribute to the classic web. It loads instantly, costs nothing to host, and carries no database security vulnerabilities. It has the simple, clean design of 1999, but it is supported by modern global CDN infrastructure and AI workflows. It is the nineties internet, resurrected and running better than ever. Grab a coffee, mind the solder fumes, and take a look around. Don’t judge the Dad jokes too hard though!