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 explainIn 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.

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​Megan Sapnar Ankerson

Megan Sapnar Ankerson is an assistant professor of communication studies at the University of Michigan.

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