Facebook chose an odd time to launch Rooms, its homage to the classic ’90s chatroom.

AOL’s Instant Messenger, perhaps the icon of the anonymous instant-messaging age, quietly killed off its chat rooms in 2010. Yahoo Messenger axed its public chat rooms in 2012, explaining only that they weren’t a “core Yahoo! product.” And when MSN Messenger shuts down Friday in China, the last place where the service still operated, it will mark the conclusive end of the mainstream chatroom era.

Sure, we have Rooms now — but Rooms, despite its branding and anonymous discussion groups, has little in common with the chatrooms of yore. And like other modern attempts to reincarnate the ‘90s chat room (Airtime, anyone?) it seems to lack that critical quality that made early AIM, Yahoo Messenger and MSN fun: the edge of quirkiness, transgression and inventiveness. The feeling that this was a new and semi-lawless space, that unexpected things could happen.

‘Web’ chat before the World Wide Web

Just look at the earliest, successful forerunner to online chat — a program that academics invented, almost by accident, long before the birth of the World Wide Web.

Talkomatic, the program’s appropriately retro name, was born out of PLATO, a computer-based education program at the University of Illinois, in 1973. It was primitive, by modern standards: Only five people could chat at once, and their messages displayed letter-by-letter as they typed. But at the time, Talkomatic was something of a revelation. PLATO had been designed for classroom use; according to its creators’ original plans, “communication between people would play [only] an incidental role.” But as more people signed on to the community, its participants began to notice something striking: In the freewheeling, pseudonymous realm of PLATO, people began to form highly personal, social connections that had nothing to do with academics. In other words, they just wanted to chat.

“People met and got acquainted in Talkomatic, and carried on romances via “term-talk” and Personal Notes,” one of its creators, David Woolley, wrote in his 1994 history of the program. “Many online personalities developed … Many people traveled to Urbana to see the lab and meet those of us who worked there … Over the years, PLATO has affected many lives in profound ways.”

Of course, PLATO could only reach so many people. But in 1980, CompuServe — one of the earliest commercial Internet services — would release its own take on the chat concept, allowing more than 123,000 to sign on nightly under screennames like “Mike” and “Silver.” (Both names are, incidentally, critical to chat room history: They were, on Valentine’s Day 1983, one of the first couples to marry as a result of online chat.)

Even though CompuServe’s “CB Simulator” was a commercial service, it shared something of the pioneering quirkiness of ye Talkomatic chats of old. The CB stands for citizens band radio — a relative of ham — and originally operated in similar ways, borrowing from radio’s lingo and channel system. In one early “channel,” described by InfoWorld in 1984, users did nothing but speak Old English and roleplay as kings and maidens. In others, a form of radical, soul-baring honesty was fairly common; between the fake names, the small communities, and the hours of online contact, the idea of intimacy became “very seductive,” one user told InfoWorld. (Seductive enough that most mainstream coverage of chat at the time focused on a phenomenon dubbed “CompuSex.”)

“To say this typewritten “human contact” or “people typing in their thoughts” is the equivalent of genuine friendship or intimacy is something else,” wrote Vic Sussman, struggling to understand the very concept of online community for The Washington Post in 1986. “It’s certainly the illusion of intimacy — the instant gratification of human contact without responsibility or consequences or actual involvement … [But] the danger is that going online instead of going into the real world ultimately turns conversation into a spectator sport.”

For users, of course, this kind of outsider bemusement was half the motivation. The Web didn’t achieve anything like mainstream usage until well into the ‘90s; before then, the people sitting through many, many minutes of dial-up bleeps and buzzes, all to talk to pseudonymous strangers, were a very particular breed: hobbyists and early adopters and other technophilic types, each drawn to this peculiar experiment in part because it was peculiar, and its results were far from known.

You never knew quite what, or who, you would find in a Compuserve chat — or, later, a chat on AOL (c. 1992), Prodigy (1992) or Yahoo (1997). AOL’s chief architect and longest-serving employee, Joe Schober, once described the earliest AOL chatrooms as “little frontier towns”: small and unpolished, perhaps, but pioneering — like a spark in the big Internet void.

The golden age of chatrooms

If the Internet was an uncharted wilderness, however, the ‘90s were its Gold Rush. Services like MSN and AOL (which bought Compuserve in 1998) made the chat function available to millions of Americans, packaging it in dial-up subscriptions that users purchased first by the hour, and later by the month. In 1993, shortly after the debut of AOL’s chatroom, the Associated Press reported, hilariously, on the “team of young, high-tech specialists” who were trying to get President Bill Clinton to host a town hall chat. (His screenname was “Clinton Pz.”)

By 1997, the year AOL launched Instant Messenger as a stand-alone chat product, the company boasted an estimated 19,000 chatrooms. Users spent more than a million hours chatting each day. And despite the panicked testimony of then-senator Herb Kohl just two years prior (“Most Americans don’t know what it is out there on the Internet,” he told a Senate committee, “and if they did they would be shocked”), the influx of new users was helping chatrooms shed their previously shady, transgressive image.

“Chat, always burdened with a slightly seedy reputation … is undergoing a major makeover,” enthused one 1997 trend piece in the Irish Times. Chatrooms were showing up in business software packages, such as Lotus and Oracle. The rooms had become a favored hangout not only of teenagers and technophiles, but of stay-at-home moms. (“Beats doing housework, don’t you think?” one frequent chat-er joked in 1996.) And companies that had previously eschewed their own stand-alone chat services, such as Yahoo and MSN, were beginning to offer their own.

What happened to chatrooms, anyway?

In some ways, in fact, chatrooms were experiencing a cultural shift similar to one much-discussed on Facebook today: a space that was once a frontier, was being standardized, monetized — colonized by moms. And the places that remained on the fringes were categorically gross: full of spam and sludge and a/s/l-style solicitation, a far cry from the supportive communities of the late ‘80s.

Combine that with the advent of new Internet technologies like DSL (which made AOL’s subscription model obsolete) and new paradigms for online social networking (think Friendster, Myspace and later, Facebook) and the chatroom’s demise was obvious, if not imminent, by the early aughts.

I remember signing into my AIM account as late as 2007, the better to chat with high school friends who had, like me, gone away for school. But by that point, all of AIM’s best features had become redundant: status messages could go on Twitter, detailed profiles could be made on Facebook, friends could be contacted via text or Gchat, people with similar interests could be found on any of the above. In 2003, MSN axed many of its chatrooms across Europe, Asia and Latin America. Over the course of the next decade, in light of plummeting usage, increased scrutiny over child solicitation and other unpleasantness, and competition from mobile and video chat, AOL and Yahoo would do the same.

“Here at Yahoo!, we aspire to make the world’s daily habits inspiring and entertaining,” chirped Yahoo!’s November 2012 announcement of the closure. “Sometimes, this means we have to make tough decisions — like closing down features that we feel aren’t adding enough value for you.”

In other words, the market had spoken: The time of the chatroom had passed. And yet, decades after the geeks of PLATO first tapped out their messages, the children of the ‘70s, ‘80s and ‘90s still illogically seem to want one.

You need look no further than Apple’s app store for conclusive proof of that: Besides Rooms, there’s the anonymous local chat app Yik Yak, the embattled, Vermont-born Omegle (which still ranks among the world’s top-3,000 sites), and the unheralded start-up Banter, which perhaps captures the spirit of early chatrooms best of the three. (“Who you are in real life is not important,” Banter’s founder told The Verge during this year’s SXSW conference. “What really matters is what you’re interested in.”)

On the modern, mainstream social network, of course, that couldn’t be further from the truth: Who you are in real life is, frequently, the only thing that matters. And in fact, that’s what makes Facebook’s decision to launch an “early Web”-inflected app so excruciatingly ironic. Facebook pioneered a system where our online identities were forever welded to our real-life ones; if the early Web was like a sparsely populated frontier town, Facebook is the planned community, the picket-fenced suburb, that followed once the pioneers had moved on. By constricting our online selves to our offline identities, Facebook basically obliterated the infinite possibilities, and the intimate, interest-based communities, of the social Web.

It’s no wonder that, 10 years in, we’ve begun to wax nostalgic over that lost infinity.

“We’re tired of being told what to do, what to see, and how to interact online by platforms that resemble rat mazes more than sandboxes,” Kyle Chayka wrote in Gizmodo. “… Like artisanal hipster nostalgia for a time when men were men, shoes were handmade, and everyone pickled their own vegetables, the internet’s vanguard is pushing for a return toward a simpler digital era.”

And so a team of unabashed idealists launched a minimalist, ad-free social network called Ello, a promise to return to a pre-Facebook web. The writer and programmer Paul Ford — who has long been a compelling voice on the culture and legacy of tech — made a super-retro Unix network called Tilde.Club on a drunken lark a few weeks ago; he was startled to see hundreds of people clamoring for invites to the thing.

“There is no need to get in on the ground floor,” Ford quipped, “because the ground floor has been there for decades.”

Even the original Talkomatic, circa ‘73, has seen a modern reboot of late: Its creators launched a pared-down Web version in March, more than 40 years after their original. It doesn’t log your chat transcripts, and it doesn’t have ads. In fact, it doesn’t have anything, really, besides a series of elongated text fields you and a friend — or a stranger! — can type into.

It’s glitchy, sure. It’s stupifying simplistic. But on an Internet where so much feels dictated and pre-determined and over-designed, it’s kind of freeing, too.