Portal of Evil was more or less a spin-off of Old Man Murray, an early gaming site affiliated with seanbaby. Old Man Murray was created by
Chet Faliszek and
Erik Wolpaw, who would go on to write Portal and others. Chet distanced himself from the running of PoE pretty early, leaving it in the hands of various users. (Pretty sure a lot of the tech side was handled by someone called
Codehappy.) Despite the seeming disinterest of its creator, the site had thriving forums that were basically Kiwifarms of the dial-up era, with similar "no cowtipping" rules (referred to then as "don't break the Prime Directive") and some of the most wonderfully obscene and tasteless humor on the web. The site
Fat Chicks In Party Hats (which I believe was a seanbaby project) was considered the peak of comedy by the typical PoE user. And much like here, lolcows (called "exhibits" on PoE) would show up and argue on the forums from time to time. Jenny was INCREDIBLY active there, posting immediate answers to petty spats over hundreds of posts. A lot of incredible early cows, like
David Gonterman the proto Chris-chan, Ben Shuman the fire alarm fetishist,
WinterRose the retarded Disney princess wannabe, Wintermist the retarded husky breeder, etc were all documented contemporaneously on PoE. Ulililia was also occasionally active there, and though he disliked PoE posters use of foul language, he was warmly received and shared many fascinating Uli insights. Now it's all tears in the rain.
Eventually Portal of Evil was spun off to the now also defunct PoE-News (originally poenews.com but somehow the domain was lost and so the site gained a hyphen) which had similar forums but centered around news articles instead of internet freaks. There was also PoETV for YouTube videos and its strange attempt at a music video aggregator, 73Q. (PoEtv is where I first encounted Invisible Crane.) I'm honestly not sure who was behind those. Poetv.com was still up as a barely functioning shell until very recently, but appears to be gone now too.
I should really attempt more thorough write-ups of both JDR and PoE sometime, but I'm a lazy sped working off of memories that are a quarter century old.
Edit to add some more off the cuff memories:
Despite the "Evil" in the name, the prevailing culture of PoE was much more "hipsters who adored John Waters and Ed Wood" sharing links to the genuinely bizarre on the early web than anything meant to condemn the exhibits. I got the impression that the site name had been chosen off the cuff in a campy MST3k kind of spirit, but many webmasters of the era took themselves extremely seriously and would get affronted at being listed in a directory of "evil" websites. However, furries correctly recognized that PoE posters were documenting their degeneracy and despised the site for that reason.
As one might expect for a hipster dominated site, there was a politically leftward trend and as the years went on the humor became less mean, it was no longer cool to call each other fags, etc. It never reached SomethingAwful cat lady levels, but by the era of PoEtv people were getting butthurt over things they used to laugh at.
One of the members of the band The Dead Milkmen was a fan of PoE. One year a furry convention was being held in Philadelphia and he posted a handful of signs reading something like "Portal of Evil extends a warm welcome to attendees of FurryCon" near the convention center. This infuriated both PoE posters and furries.
Lolcows such as 2 the Ranting Griffon, the cartoonist behind Faithmouse, Usagi Kou, AlyssaKiss, and Imari Stephenson all had feuds with Portal of Evil. The Faithmouse guy eventually became a regular poster. I will probably think of several more immediately after hitting post.
Edit edit: Pretty sure the
Bob's Game guy was the last major "lolcow vs Poe" incident.
I vaguely recall the Wintermist husky lady,
Kimberleigh Ann Keister, leading to some kind of moral panic on the site, but my memory is shit. A lot of PoEsters got waaay too excited about a retarded furry, I think because she was making grandiose claims of being a dog breeder and there was a PoE poster who was part of the dog show world who debunked her bullshit. But people got obsessed, not unlike how people got obsessed with Chris in the early days, and I think it started to spiral into trolling attempts against the spirit of the site, or at the very least people felt there was some kind of line being crossed as far as deliberating posting shit intended to send a genuinely retarded woman into a rage spiral for lols. There was a cartoonist who had been a forum regular for years who had drawn some pretty funny art of Kim Keister and then had a total breakdown over it and was never heard from again, iirc. Shortly after the forums were taken offline for maintenance and were put back up kind of broken and posting started to move to PoE-News.
PoE people really really loved
Achewood. Bad webcomics were a favorite target, but Achewood was
beloved. This may or may not be a meaningful insight into the culture.
Final edit: One PoE catchphrase that will live on in my brain forever is "Why in the ass? Why more than ten times?" This was referenced and parodied quite a bit. The inspiration was a Geocities page featuring unfortunately terrible poems from a woman who'd gotten out of an abusive relationship. The poems were formatted in garish colors with midis of songs like Dragula looping in the background. The dissonance between the subject matter, the clumsiness of the poems (one of which asked repeatedly "Why in the ass? Why in the ass instead of the vagina? Why in the ass? Why more than ten times?"), the very web 1.0 presentation, and the shitty heavy metal midis was something to behold. Nobody really knew how to use the internet yet.
Archive of post from Chet announcing the closure of the original forums, aka PoE-Red. I wish I had any insight into the legal issues he references, but I don't. The "Thor" mentioned is cartoonist
K. Thor Jensen, who did a lot of the running of the site.
Article from Thor about the site.