On the cover of WIRED's eighth issue, the Pillsbury Doughboy stands against a wall, flanked by two men wearing neckties. All are blindfolded, stricken with terror. Together they face a firing squad of mismatched TV remotes. The cover line reads: “Is Advertising Finally Dead?”

February 1994

By all appearances, the cover promised yet another gleeful epitaph for the declining institutions of the analog age. In just over a year, WIRED had already predicted the imminent demise of public education and The New York Times. Michael Crichton proclaimed in the fourth issue that “it is likely that what we now understand as the mass media will be gone within 10 years. Vanished, without a trace.” Advertising, it seemed, was the next industry marked for obsolescence.

But the cover story itself—an essay by MIT Media Lab fellow Michael Schrage—was not, in fact, an epitaph at all. Instead, the article imagines how advertisers will adapt to, and eventually come to dominate, digital media. Read with the benefit of hindsight today, the piece has an almost Cassandra-like quality, foretelling a future both unpleasant and unavoidable—a future that feels a bit too much like now. It may be the most eerily prescient story that WIRED published in its early years.

How do I know? This past summer, I pulled up a chair—for a time at the Library of Congress—and read every issue of the magazine’s print edition, chronologically and cover to cover. My aim was to engage in a particular kind of time travel. Back when founding editor Louis Rossetto was recruiting the first members of the WIRED team in the early 1990s, he said he was “trying to make a magazine that feels as if it has been mailed back from the future.” I was looking to use WIRED’s back catalog to construct a history of the future—as it was foretold, month after month, in the magazine’s pages.

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In part, the fun was in recognizing what WIRED saw coming—the flashes of uncanny foresight buried in old print. Back in the mid-’90s, a time when most Americans hadn’t even sent an email, the magazine was already deep into speculation about a world where everyone had a networked computer in their pocket. In 2003, when phones with cameras were just a novelty in the US (but popular in Asia), Xeni Jardin was predicting a “phonecam revolution” that would one day capture images of police brutality on the fly. Just as interesting were the things WIRED saw coming that never did. The November 1999 cover story held up a company called DigiScent, which hoped to launch the next web revolution by sending smells through the internet. (“Reekers, instead of speakers.”)

But more than just scoring hits and misses, I was interested in identifying those visions of the future that remained always on the horizon, the things that WIRED—and, by extension, the broader culture—kept predicting but which remained always just out of reach. Again and again, the magazine held that the digital revolution would sweep away a host of old social institutions, draining them of their power as it rendered them obsolete. In their place, WIRED repeatedly proclaimed, the revolution would bring an era of transformative abundance and prosperity, its foothold in the future secured by the irresistible dynamics of bandwidth, processing power, and the free market.

At the same time, an animating tension has always run through the magazine, one that stretches all the way back to Schrage’s 1994 essay. The cover loudly suggests the death of the analog order; the text anticipates how the old order will adapt, graft itself onto the digital revolution, and alter its trajectory. Cutting against the magazine’s exuberance—but also propelled along by it—is a heretical strain of ­gimlet-eyed, anxious ambivalence about who will pay for the future. It’s this tension that has produced some of WIRED’s moments of greatest foresight.