How Coolness Defined the World Wide Web of the 1990s

Before the NSA revelations and Buzzfeed listicles, there was the early web. And it was an incredible blend of personal, mundane, and extraordinary.

A row of iMac computers at the 1999 Macworld Expo convention (Reuters)

Summer is the ideal season to contemplate that perennial, overused, and ever-elusive concept of cool. This summer is particularly ripe, for August marks the 20th anniversary of an early web phenomenon known as “Cool Site of the Day”—or CSotD for those in the know.

If you weren’t online in the mid-1990s, you might have missed the tremendous effort devoted to curating, sharing, and circulating the coolness of the World Wide Web. The early web was simply teeming with declarations of cool: Cool Sites of the Day, the Night, the Week, the Year; Cool Surf Spots; Cool Picks; Way Cool Websites; Project Cool Sightings. Coolness awards once besieged the web’s virtual landscape like an overgrown trophy collection.

These recognitions were regarded as welcomed honors, visually stamped on the distinguished site with a graphical status icon that bestowed a mark of “quality.” Accumulate enough of these accolades and new awards.html pages would be erected to showcase the entire collection.

Examples of “cool” award icons, 1994-1996

Maybe today’s users find the early web’s preoccupation with cool to seem little more than the juvenile boasting of Internet novices. But a closer look at sites like Cool Site of the Day, and the countless other cool directories like Netscape’s "What's Cool?" and Yahoo!'s Cool Sites listing, might actually tell us something about how and why networked technology and digital culture forged such an enduring link to the concept of cool.

The value and ambiguity of “cool” offered a strong but imprecise language that helped users grapple with the feeling of navigating networked media at a moment before the web experience had yet to be fully habituated.

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Launched on August 4, 1994, by a projects manager named Glenn Davis at the Virginia-based Internet Service Provider (ISP) InfiniNet, Cool Site of the Day was a simple concept that soon inspired a host of imitators. Davis announced his venture on a number of UseNet newsgroups with the following post:

Need a daily fix of something new? Try The Cool Site of the Day. Every night at midnite the Cool Site of the Day gets set to point at a new Cool Site. You’ll never know what’s there until you take the link so expect to be surprised. 

Cool Site of the Day, August 31, 1995

With this, “cool” was serialized as a daily ritual, a hand-picked hyperlink to somewhere new and unexpected. As the wry commentators of the off-beat 1990s website remarked, CSotD was “built on three blindingly obvious propositions: it was daily, it was cool, and there was nothing there except the goddamn link.” The site made Davis one of the first Internet celebrities and CSotD became known as the web’s “arbiter of taste.”

At the heart of CSotD was the “surprise” element of a cool link, concealed behind the stylized cyber-slang that was so pervasive at the time (e.g. “SlursDay, AweGust 31”). Browsing the archive of Cool Sites selected in 1994, one might surmise that the element of surprise is partly related to the vast range of content that is featured—a hodgepodge so arbitrary that it appears hard to draw out any defining characteristics of cool.

In that first month of operation, the cool links feature sites as diverse as the Froggy Page (“filled with froggy fun!” including frog pictures, sounds, stories, and scientific information), a repository of downloadable music, a website for Chevrolet, a virtual pub, the Web Louvre museum (later renamed because it was not actually created by the Louvre), the San Francisco Examiner, a home page for the city of Austin, Texas, and fan pages devoted to Monty Python and Tori Amos, respectively.

Day after day, the quirky followed the serious, small sites mixed with vast resource databases, work produced by amateurs was featured alongside that of IT professionals, and the most trivial content sat side-by-side with useful productivity tools. Faced with such incongruities, one might wonder if there can even be a cohesive logic of cool.

Perhaps it’s this very ambiguity and flexibility that makes the slippery subject of “cool” a matter of ongoing cultural reflection. Slate devoted a month-long series to the history and future of cool last year. This year, the Smithsonian’s National Portrait Gallery is featuring a new exhibition on “American Cool,” a collection of iconic photographs of 100 Americans deemed to exemplify cool’s allure: “to be cool means to exude the aura of something new and uncontainable,” the curators explain. In Cool Rules: Anatomy of an Attitude, Dick Pountain and David Robins detail cool’s historical legacy as a stance of individual defiance, a pose by social outsiders who conceal rebellion behind a mask of ironic detachment that guards against emotional excess.

As a bundle of contradictions combining disaffection, accommodation and resistance, cool moves deftly from the margins to the mainstream, making it notoriously hard to pin down.

This hasn’t stopped the steady output of critical musings on cool’s mysterious complexity: scholars have traced its roots in African culture that were ported to America with the slave trade, its connection to Black culture, music and masculinity, its embrace by Beat poets, intellectuals and other disaffected rebels, its incorporation into advertising and consumer culture, its partnership role in the perpetual resilience of capitalism, its ethos within post-industrial information labor, and its broader historical development as a specifically 20th-century emotional style.

How did we get from this legacy of cool to contemporary uses of the term? “Cool” has become an all-purpose descriptor for anything loosely agreeable, or an accolade typically reserved for high tech gadgets, software start-ups, and smartphone apps (a regrettable dilution of cool bemoaned by some commentators). Today's cool seems severed from 20th-century cool. Yet, in returning to the zeitgeist of digital cool that sites like Cool Site of the Day helped to popularize, we find some semblance of a connection that links tech culture and everyday life.


Twenty years ago, the web was still very much a hobbyist pursuit. The dot-com boom, typically dated to the Netscape IPO of August of 1995, was still a year away. In fact, the Netscape browser had not yet been publicly released. Getting online was no easy task in those days. To find one’s way to the World Wide Web required setting up a SLIP or PPP connection, acquiring a modem and configuring ports, firing up the terminal window, typing arcane commands, using the file transfer protocol to download, install, and configure a web browser like Mosaic (a precursor to Netscape Navigator). And then, when finally on the web at long last, there was no easy way to discover what it was that others were even raving about.

In the days before search engines, web surfers were at the mercy of links to guide their travels through the network. Testimonies from the web users of 1994 describe the experience of jumping around the network as one of intense dislocation, both thrilling and excruciating. The endless, aimless, wandering through a maze of hypertext links was a solitary pursuit, but it was also very much a social experience. Describing the “vertigo of Net travel” in a 1994 article for Wired magazine, Gary Wolfe writes:

It was a type of voyeurism, yes, but it was less like peeking into a person's window and more like dropping in on a small seminar with a cloak of invisibility. One thing it was not like: it was not like being in a library. The whole experience gave an intense illusion, not of information, but of personality. I had been treating the ether as a kind of data repository, and I suddenly found myself in the confines of a scientist's study, complete with family pictures.

Finding the web was a strange encounter: it involved dwelling in the intimacy of virtual strangers and parsing the distinctive and amusing jargon of cyberspace. Press accounts intended to introduce a more general public to the web often played with the language of cyber-slang as way to inject humor and orient readers to the peculiar cultural forms and communities that could be found online. “Hey!” begins one article from The Independent, “Last night I net surfed through cyberspace, flamed a few people, swapped some hot chat, hung out in the usual places. You know… Being on the Internet is cool, ok?”

To call the web of ’94 “cool” is to offer a semantic bridge that linked the elusive familiarity of something “new and uncontainable” to the peculiar temporal and spatial experiences of web surfing with all its secluded sociality and sudden juxtapositions between the valuable and useless “free fun stuff!” that could be found in abundance online.

Returning to Cool Site of the Day and other early cool-site collections, we find links to movie trivia and webcams trained on fish tanks, mortgage calculators and email syntax guides, clip art collections, and NASA images of outer space. You could play a hand of blackjack, peruse Bartlett’s database of quotations, pose a question to the Magic 8 ball, and answer an online personal ad. There were satellite weather maps and feminist music communities, sci-fi enthusiasts and BDSM aficionados, geek subcultures and mainstream marketers—a cacophony of weird things, helpful tools, unexpected resources, and diverse voices made to seem suddenly close, personal, and rendered in rich detail.

Taking the attributes of each “cool site” on its own, we might be hard-pressed to make sense of what exactly it is that makes any selected site truly worthy of cool. But viewed as a collection, cool sites were those broadly in tune with the ethos of the web. It was precisely through the arbitrary juxtaposition of the various links presented each day that the contours of cool found footing in cyberspace. This ecosystem of cool sites gestured towards the sheer range of things the web could be: its temporal and spatial dislocations, its distinction from and extension of mainstream media, its promise as a vehicle for self-publishing, and the incredible blend of personal, mundane, and extraordinary that was encountered in the course of surfing the web.

The idea of “cool sites” may seem dated today, in an age when cool seems ever more fickle and fleeting. Today we have ubiquitous listicles of “12 cool must-have apps” or “top coolest gadgets of 2014.” But I can’t help feeling that there is something enduring about the early web’s legacy of techno-cool that lives on when I find myself marveling at so many “utterly useless apps you don’t want to miss!” How our smart phones can help us do something so dumb! And how, at the same time, when our location in space and time is merged with other sources of data, these devices and apps can surprise us with glimpses of things curious and unexpected.

Yes, in an era of incessant upgrade culture, when we are constantly made to feel as if the next new thing is quickly passing us by, the cold hand of cool is tightly clasped in capitalism’s embrace. But cool’s evasive contradictions, its pleasures in operating both inside and outside of the market, its desire for cheap thrills, fun stuff, and new experiences does, I think, find something recognizable even within the confounds of Google Play and the Apple App Store. There we can find simulated staplers that “satisfy the urge to press without wasting staples,” virtual lighters that allow you “to play safe with fire,” retro dialers that convert your smart phone into an old-fashioned rotary dial.

You can install a GPS-enabled tombstone finder! Instantly identify birdcalls, constellations, traffic patterns, song titles! Chat, connect, and hook up with potential romantic partners! Receive alerts five minutes before it will start raining in your exact location!

Wow! It’s all so… cool?