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Unraveling the web's story

The Web and the Webbys Grew Together

The modern day webby awards logo

The Webby’s are an award show, (in)famously billed as “The Oscars of the Internet.” They’ve been running since 1996 which, as regular readers will know, was pretty much right when the web got up and running. The thing about the Webbys is if you trace it back, you’ll find your hand running along the contours of the web’s early history. Its transition from a modest gathering of outsiders to a lavish, celebrity-packed spectacle more or less mirrors the web’s transition from something virtually unknown beloved by only the geeks to a fully universal technology.

It has also, over the years, been a matter of some controversy. A common criticism, articulated most publicly by Nick Denton in Gawker, and then a year later in Slate, is that the award show is a pay to play scam (entering to win a Webby requires you to pay a fee) that props up marketing firms and large corporations at the exclusion of truly interesting indie nominations. Writing in 2012 in Wired magazine, Andy Baio offers a more nuanced contention. His main point is that the Webby’s are an event that was created by the advertising industry for the advertising industry so it’s really no surprise at all that it tends to take on a commercial bend and charge an entry fee.

And yet, the first few Webby’s were kind of fun. For everyone. They featured an eclectic mix of the larger sites that bear the brunt of criticism alongside indie, experimental challengers and singular efforts. They had a fairly unique gimmick when they limited winners to a five word acceptance speech to move things along. And the crowd always got into it, and the winners accepted their words with a bit of nerd flare.

The founders of Google at one of the earliest Webby awards

It was only years later, when the then-dead Webby’s were resurrected from the ashes of the dot-com boom that it turned into more commercial territory. There, at least, the common criticism is somewhat valid. But a bit of selling out is to be expected for something that runs for a while, stops, and then tries to recapture its former glory.

The story unofficially begins with Cool Site of the Day, which launched in 1994. As the title suggests, each day it would feature a cool new site on its homepage. Getting your website on that homepage could mean tens of thousands of eyeballs. Not a lot by today’s standards maybe, but in ’94, that was pretty much everyone on the web. To boost the site’s popularity, Kay Dangaard was tapped to produce the first official ceremony for a brand new award, the Cool Site of the Year award, or just Webbie for short. She chose to host it at the Hollywood Roosevelt Hotel, the location of the very first Oscars ceremony 65 years earlier. The Spot, a kind of soap opera on the web, was the first site to win a Webbie.

Rather than a direct ancestor, the Webbie was more a spiritual successor to the modern day Webby’s. Those got started when Web Magazine decided to take a crack at their own version of the idea (incidentally, the award show would last. The magazine would not.). They asked filmmaker and marketer Tiffany Shlain to run it. She created a list of categories, gathered nominations from the staff at Web, and selected a panel of judges to pick a winner for each one. The first official Webby’s were held in March of 1997 at the Bimbo’s Night Club in San Francisco. It was a fairly small affair, though it was not without a bit of fanfare. Mayor Willie Brown opened the ceremony, and it was broadcast on the locally syndicated show Net Cafe.

Tiffany Shlain hosting the ’97 awards

Net artists Auriea Harvey and Michaël Samyn, the brand new online-only magazine Salon, and an early version of IMDB were among the winners that year. It was hosted by Shlain herself, her own brand of offbeat tech humor echoed by an excited, techno-savvy audience. It had a handful of unique and interesting categories, like Weird and Sex. The Webby’s didn’t take themselves too seriously, and at the time, the web didn’t either. The idea of the web as a serious thing hadn’t even really occurred to anyone yet and the Webbys reflected that quite well.

The following year, in an attempt to legitimize the ceremony somewhat, the International Academy of Digital Arts and Sciences was created by Shalin and a few others specifically to select nominations and winners for the the Webby awards. The IADS counts a number of celebrities and tech pioneers among its members.

The 1998 Webby’s had a bit of a different edge to it. It was, for instance, the first to be livestreamed from the website. The number of categories was bumped up, and the Sex category was removed altogether. The whole thing picked up and moved to a larger venue to host an expanding list of potential guests, many from outside the tech world. In some ways, it was the same Webby’s, just a bit buttoned up.

There were still plenty of nominations from a number of stranger, more personal sites built by small teams or even individuals. But these were mixed in with websites fronting massive, established media companies, like CNN, PBS, and Disney. In most cases, these sites were being built by small teams inside of these companies, who, as individuals, were very much dedicated to the web, like the team at PBS who managed to ditch a multi-million dollar proprietary Internet software gambit in favor of the open source web browser. They won a people’s choice award in 1997, and then were official winners in 1998. These were internal web advocates who deeply believed in the potential of the web, that used the Webby’s as a way of legitimizing their work internally. Still, to some extent on the outside, it looked as if the suits had crashed the party.

The next year, in 1999, the Webby’s became a full-on spectacle. It once again moved to a larger venue, and transitioned to a black tie, red carpet event. The broadcast featured celebrity interviews, and a behind the scenes look at the ceremony itself. It had a celebrity host (comedian Marc Maron) and accompanying MC (Marina Berlin). It was also the first year to add what’s now became a feature of the Webby’s: the five word acceptance speech. With an all-time high of 22 categories to get through in an hour, the five word speech was an interesting gimmick that served the entirely utilitarian purpose of keeping things moving.

Marc Maron at the ’99 awards

In the most poignant moment of the evening, the artist collective, receiving their award for the Net.Art category, aggressively pushed past a cameraman to get to the stage to deliver their own acceptance speech:

Ugly commercial sons of bitches

The moment was, at least in part, a staged outburst, the artists clearly miming their aggression with their stunt and the whole thing was performative and overblown. And yet, it put a fine point on the evening. Its subtext, or I guess in this case actual text, was more than sincere. In the eyes of some, the occasion was just one more symptom of a web’s commoditization as pieces of the web were being chunked up and sold for profit.

By year 4, at the turn of the century, the event had gone fully commercial. It was held on May 30, 2000 at the Masonic Center in San Francisco, with 3,000 guests in attendance. There was a $30,000 cash award. The number of categories was bumped to 27. The New York Times covered the event. Alan Cummings was the night’s MC and there were a number of celebrity presenters. There were dance performers and fake paparazzi. Sergey Brin, one of the founders of Google, rollerbladed on to the stage to receive his award in Technical Achievement. The whole thing was just a bit much. It was the year of peak Webby’s.

The original Webby Awards logo

What’s important to understand, though, is that the tech industry had reason to be excited. There were plenty of wonderful, strange, and exciting things happening on the web. Some were in the commercial world, and others were just interesting experiments. But the rapid pace of development the web allowed for was changing entire industries. The commercial potential of the web had begun to be realized, and more than a few companies had started cashing in. Every day it seemed like a new startup opened its doors with its sights set on changing the world and raking in massive profits. In the year 2000, many hyped techno-futurists thought they were standing on the precipice of a massive transformation, not to mention a proverbial gold mine.

Indeed they were, just not the one they thought. That year marked the beginning of the dot-com crash, a catastrophic shift that would see an investment bubble in web-based companies that had been building for years finally burst. It forced many companies to close their doors. One fifth of the winners of the 2000 Webby’s were among those that had to shut down that year. Many of the nominees were among that group as well.

Like it always did, the Webby’s followed the web. In 2002, the ceremony was scaled way back. In 2003 and 2004, without the means for a physical venue, it was hosted entirely online. It wasn’t until 2005 that the award show was fully revived in New York City. This time, it was riding the crest of the Web 2.0 wave, as proprietors and businesses awoke from the dot-com stupor and began to reinvest in the future of the web.

And since then, the Webby’s have grown, though they look a bit different these days. There are dozens of categories now, with special buckets for Social and Marketing sites. Celebrities are almost always in attendance and many get on stage to receive awards of their own. It is, as it has always been, a reflection of a new kind of web, one that is used by everyone.


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