When Jim Crawford released a browser game named Frog Fractions in 2012, half the people who played it called him a genius; the rest thought he was deranged. What most of them seemed to agree on however, was that they loved it. When influential site Rock Paper Shotgun covered the game, it did so under the header: “Frog Fractions might be the greatest game of all time”.

Unpredictable and absurd, Frog Fractions starts out under the guise of a piece of edutainment software in which you control a frog sat on a pond scooping up bugs and defending fruit. Then after buying a few upgrades, you’re suddenly riding a dragon through an underground tunnel that takes you into Crawford’s own bizarre version of video game wonderland. Many read it as a comment on the absurd conventions of video games. Many others read it as weird frog game.

Whatever the case, most players thought Frog Fractions would be a one-off, a weird, singular piece of outsider art. However, in December 2016, Crawford announced his intention to release Frog Fractions 2. He’d spent two and a half years working it out, going back through the past 20 years of his life, surfacing everything he could to bundle everything up into a single video game. By the time it was released, Frog Fractions 2 was practically an interactive autobiographical portrait of the author.

Who would do something like this?

Frog Fractions Photograph: Jim Crawford

Currently living with his fiancee in Castro Valley, California, the 37-year-old Crawford isn’t quite the colourful clown you might expect him to be. Humble and ponytailed, he speaks over his glasses as he cranks out a stream of one-liners about really, really liking soup (one of his elaborate running gags). He pursues his lifelong interest in making games from home, or at least whenever he can manage to focus on doing so. “I’ve been a hardcore dilettante all my life,” he shrugs. He’s a man with an erratic attention span, who has a history of getting bored by a project and moving to the next one without finishing it, a man who spends his time hopping between hobbies. He doesn’t know why he can’t sit still.

If there’s one constant in his life it’s his love of programming. He can trace his interest back to sixth grade, when he randomly picked up a book that listed code for games made in BASIC. “I remember skimming through it and getting excited that it all seemed pretty intuitive to me, and that I wanted to do this sort of thing,” he says. “My divorced parents conspired together to get me a Commodore 128, and programming was instantly my primary hobby from then on.

“Programming clicked for me in a way that felt very primal, like acquiring an additional sense, becoming one of the fundamental ways I interact with the world.”

What helped to keep programming at the forefront of Crawford’s interests is its application in other creative fields. His understanding of programming widened in 1992 when he encountered the demoscene – artists and programmers who create impressive audiovisual sequences under tight computer memory restrictions. Crawford’s uncle showed him the demo Unreal, made by Finnish demogroup Future Crew, and that was it, he was hooked. “I was exactly the right age and temperament to be blown away by this sort of thing,” says Crawford. “Watching talented people strain against the limitations of an underpowered CPU is goddamned inspiring.

“At the time I saw Unreal, I lived in Princeton, New Jersey and, presumably by some security oversight, the university just let people wander into their computer rooms and use the hardware. I spent a lot of time there. After I figured out that I had to set the FTP client to binary mode, I downloaded all the demos and all the source I could find, and dove into real-time graphics programming. I got good enough to impress my friends, but never felt like I was good enough to really be a part of the scene.”

The next programming deviation came in 1995, when Crawford discovered Scream Tracker 3, and used it to make electronic music that he shared with friends. He got so into it that he joined the #trax IRC channel and attended a few demo parties, but he grew frustrated with his inability to make proper friends in that community, and eventually drifted away.

Since then, Crawford has dabbled in learning various musical instruments, but only ever got anywhere with drums. He also spent a while building his own electronics, some of which he began making music before he moved on to his next pursuit. Over the years he’s continued to jump between hobbies like this, picking up new skills and interests, which explains why Frog Fractions is structured like it is. Once its mad descent begins, it starts to cycle through game genres before you can get a grip on any one of them: it’s a shoot ’em-up, no it’s a courtroom drama, oh wait now it’s a text adventure. This smorgasbord of game mechanics and scenarios is a direct imprint of Crawford’s wavering attention span.

Without that chaos, it’s likely that Frog Fractions wouldn’t even exist. It came at a crucial time in Crawford’s life, not long after the life-changing promise he made to himself in 2010: “I decided it was a priority for me to actually ship games and actually have people play them,” he says. This was unprecedented. As a child, Crawford spent years reiterating the same platformer engine, never actually making a game with it, “because when it came time to actually take the engine and make a finished game out of it, it was a bunch of art and level design work I was scared of.”

Despite struggling to finish making games, Crawford dreamed of being paid to do it full-time, and he pursued this ambition until 2005, the year he landed a position at a game middleware startup. “It had the combined stresses of a startup and an R&D department doing cutting-edge work,” he says. “I just didn’t have it in me to dedicate the time and energy it demanded. I was let go after six months, and I relegated game dev to hobby status.”

What changed in 2010 to encourage Crawford to make that promise of finishing games to himself was that the web design company he worked for in San Diego, California was slowly cutting his hours as it went out of business. He realised he had to do something to break his habits and railroaded his goal by working in Flash, “the lowest barrier to entry platform for players at the time”. He concentrated on projects small enough to hold his attention span, and by forcing himself to stop dwelling on code quality. “The first thing I shipped, Futility Pong, took about a day of work. The next, Futilitris, was probably a week’s worth of man-hours, spread over a month,” Crawford says. “I also did a bunch of game jams at the time, which helped reinforce the ethos of getting lots of small things done fast.”

At some point, Crawford began to weave his small games together under a single identity. “I stumbled into Frog Fractions as a larger scale project that could keep my attention, by sheer dint of its variety,” says Crawford. “If I felt like building a text adventure, I damn well could, and it’d fit the project.” Everything seemed to come together. He was even able to use some of the music he had made between 2001 and 2012 as the game’s soundtrack.

When it came to making Frog Fractions 2 in 2014, however, some of the energy that pulled together the multiple parts of the first game had been lost. One issue was that Crawford had decided to hide the game inside another one, a fairy-themed city builder called Glittermitten Grove. Unfortunately, this made it difficult for him to introduce a protagonist capable of carrying the rest of the game forward. This was only the start of the difficulties.

Frog Fractions 2 Photograph: Jim Crawford

The development process of Frog Fractions 2 was somehow more intentional and yet more chaotic. The original had made Jim Crawford the Frank Zappa of video games, and expectations were high, but Crawford was confident he could deliver due to the improvements his life had seen. “Frog Fractions was itself a huge inflection point in my life, because the reputation it gave me as a designer gave me the means to make games on my own terms – with creative control, and with working hours appropriate for a human being,” he says.

In April 2014, Crawford used that reputation to raise $72,107 (£58,254) on Kickstarter towards the development of Frog Fractions 2. That meant he had people actively invested in the game being finished and it being entertaining, which added to the pressure. Crawford was not really set up for that. “I haven’t had a consistent work schedule since I was laid off from my day job in mid-2012,” he says.

He does have a few “constraints” in his daily life: a co-working event at The MADE every Tuesday, a podcast with the Kingdom of Loathing developers on Wednesday evenings, a fiancee to spend time with outside of her day job. But the rest is what Crawford describes as a “free for all”. He had to battle the distractions of his mind while managing to properly dedicate time to work on Frog Fractions 2, as well as oversee the two alternate reality games (ARG) that accompanied it. These involved 23 other indie games on Steam, with developers hiding puzzle pieces about Crawford’s sequel in their own projects. In one incredibly staged moment, the ARG broke out into real life, with a letter from a “time traveler” turning up in a library book in Berkeley, California. The time traveller then kidnapped Crawford in front of spectators who managed to piece together the clues to the surreal piece of marketing theatre.

In the end, those two ARGs were taken over by designers Justin Bortnick and Erica Newman. Crawford had moved on. “I suspect I’d be more productive if I had a fixed schedule, but I also suspect I’m happier like this,” Crawford says. “There was a pattern I’d observed in my late 20s, when I was comfortably in day-job mode, that time seemed to be accelerating, and that I might be on my deathbed and it would all feel like an eye-blink.

“I haven’t felt that way since Frog Fractions, and I suspect it’s the tumultuousness and unpredictability of my life,” Crawford continues. “Some of that comes from the drama that falls out of the Kickstarter, of course, but also a lot of it is just that I don’t really plan my life: it just happens to me, and I don’t really know what to expect.”

Frog Fractions 2 was born out of contained mayhem. Crawford initially spent a year working on a number of small prototype games that were unrelated and varied in their quality. “My usual mode of operations is to create chaos and try to tie it together into something coherent only when absolutely necessary,” he says. Seeing that his work was getting out of hand, he eventually sat down in early 2015 to organise it into a single package, ensuring Frog Fractions 2 would have a build for PAX 2015.

At this time, the sequel was playable but not necessarily something that anyone other than Crawford could comprehend. That sounds like it was a failure but, in part, it was meant to be that way. “It’s probably meaningful that Frog Fractions was ‘outsider art’, and after Frog Fractions, I suddenly became very much an insider, and I mentally compensated for this by making my allusions more wide-ranging and esoteric,” says Crawford. “That’s why the hub world [in Frog Fractions 2] is a mashup of ZZT, Insanity, and DROD, three PC games that I loved, but very few people have played.”

Frog Fractions 2 Photograph: Jim Crawford

Moving out from that hub world, Frog Fractions 2 only becomes more obscure as genres are picked up and dropped suddenly, and story arcs are cut off without warning. Some reviewers found it too stretched and confounding, others loved the maelstrom of ideas. One moment you were playing a Flappy Bird pastiche, the next it was asking you to install your Mass Effect 2 save. Nobody really makes games like this. William Pugh and Davey Wreden have questioned game tropes and broken the fourth wall in titles like Stanley Parable and Beginner’s Guide, while titles such as Jazz Punk and Thirty Flights of Loving play with conventions. But Crawford brings in the surrealist anarchy of psychedelic rock.

At some point, while playing through Frog Fractions 2, the references and digressions will probably lose you; it steers itself into complete chaos and drags you in with it. This is where Crawford wants you, it’s where he’s most comfortable, as it’s from there that he can engineer moments of true surprise. If there’s one thing you can rely on when playing one of Crawford’s games, it’s that, if you’re lost, then you’re exactly where you’re supposed to be.