Hypnospace Outlaw, the next game from Dropsy developer Jay Tholen, is a bit of a creative accident. The odd, retro-digital aesthetic of the game wasn’t meant to be the whole point of it. As I learned emailing him, Hypnospace’s virtual computer started out as little more than window dressing.

The original idea was much simpler: Players would chase and apprehend internet criminals on a virtual information superhighway. What is now Hypnospace’s elevator pitch is how users interact with its strange, funny, Windows 3.1-era operating system from the early ‘90s, including a period-authentic representation of the web.

“The operating system served as more of a level select screen for players to pick which outlaw they’d pursue next,” Tholen says. “I had so much fun populating it with a fake-internet and interactive doodads that it became the main draw of the game.”

Of course, using the internet, and even a computer, was a vastly different experience 20 years ago, with dial-up modems that could take two minutes to even connect online — not to mention the primitive state of webpages. To anyone that remembers those days, they’re impossible to forget: full of rudimentary low-res animation, flashing clip art, and plain text content. The line between the actual page and junk ads was pretty blurry.

“My early experiences on the internet are hugely inspiring,” Tholen says. “The point at which it became just accessible enough for some grandma somewhere to create a virtual shrine to her deceased dog fascinates me. It was a bit of a Wild West situation, and it’s neat perusing old Geocities archives just for the creativity folks employed before social media came around and homogenized everything.”

Recalling (in a sense) Papers, Please, the outlaws you track make hideouts from this kind of thing, with players gaining jurisdiction over an increasingly wide legal swath. Of course, there’s more to the game than simply monitoring the internet — using programs on the computer’s OS itself plays a vital role, including virtual pets, hallmark electronic playthings of the time. Again, Tholen’s personal experience is driving what he wants to share with players.

“I had Tamagotchi, but I killed it relatively quickly and never picked the poor thing up again,” Tholen says of the quintessentially ‘90s tech. “Shifty freeware that may or may not infect your computer with a virus, useless toolbars, and adware were integral to my Web 1.0 experience, and I wouldn’t deny my players the pleasure.”

Contextualizing the literal first-person interface of Hypnospace with the point-and-click design of Dropsy, Tholen’s debut game about a misunderstood clown, you might guess he played a lot of the genre growing up, and you wouldn’t be wrong.

“Most of the adventures I’d played were shareware versions I’d nab from the various thrift stores my mom would drag me to. I’m not sure I remember ever having the full version of anything other than Hugo’s House of Horrors until I was old enough to buy stuff myself,” he says. “We were pretty rural and didn’t have a local store that stocked PC games for a while. When you’re stuck with demo versions, you’re left with a lot of room to imagine what might be possible in the later portions.”

Still, Tholen says he’s not actually that interested in strict point-and-click design as a creator.

“While I love that adventure games can tell stories without having to explain why players are just repeating one core mechanic — shooting people, collecting gems, etc. — endlessly, creating one isn’t much fun after the planning and iteration stages are over,” he says.

He gives the example of item interaction between characters, where every outcome has been programmed and narratively accounted for.

“If anything unexpected happens, it’s a bug,” Tholen says.

Given these restrictions, it’s clear why Hypnospace appears to take on a more dynamic style of design.

“While developing Dropsy, I pined for something with tactile, playful elements, or dynamic systems players could mess around with,” he says. “I love playing traditional adventures still, but they’re definitely taxing to create and balance.”

Photos via Jay Tholen

Steve Haske is a Seattle-based writer and sometimes a creator of stupid art. His work can be found on VICE and Playboy. Iain Glen is his Virgil.