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The Webby Awards
In 1996, Tiffany Shlain founded the Webby Awards, the leading international honors for websites. As the creative director and business leader for nearly a decade, Tiffany, along with a core team, built the Webby Awards into a global institution and industry bellwether, known as "the Oscars of the Internet." Today it approaches its 29th year of shining a spotlight on the best of the web.
My Journey Founding the Webby Awards
My first vision of the web was in the '80s, when I was at Redwood High School. I had the first Apple computer, the MacIntosh, and I could connect via modem to the library (and just the library). The thrill of that connection was intoxicating and soon I was thinking about the potential future of personal computers directly connecting all of the world. I co-wrote a proposal with a fellow student titled "Uniting People in Telecommunications and Software" (UNITAS.) The idea was that if students from enemy countries (America, Russia, and Iran) could communicate and show our shared interests we would see how much we have in common and hopefully help pave a pathway to a more peaceful co-existence. I sent this proposal to Congresswoman Barbara Boxer in 1987 which led me being invited to be a Student Ambassador to the Soviet Union in 1988 through a program called The People to People Student Ambassador Program. This trip was also a way for me to return from the land my grandfather George Shlain escaped from when he was 16; the rest of his family was killed for being Jews. I had always wanted to travel back to Odessa, Ukraine to see if there was anyone left and understand more of my family roots. When I arrived in the Soviet Union, not only did no one have personal computers, there were lines for food and I was unable to find any remaining family members. It was a profound experience as a teen to experience a country in such duress, not find discover my roots, and see how this idea of personal computers being linked together in a network was very far away.
This was the summer before I started UC Berkeley. For the next four years as an interdisciplinary studies major, I studied the interconnections between science, the humanities, and discovered a passion for filmmaking. Right after graduating, I started work on my first feature film, Zoli's Brain, a surrealist film about an artist going through a creative block where all the metaphors of the mind were taken literally. We shot in Alcatraz, where ideas were imprisoned in "brain cells." There was a Peace of Mind Patrol that served to keep the order and fantastical characters like the Mother of Invention. There were 40 locations and over 200 actors and a mostly all-volunteer crew. I kept going into production and then running out of money, and needing to take various jobs (waitress, professor’s assistant, and eventually producing CD-ROMs) to make more money to go back into production.
Since technology had always been a passion of mine, I started working on CD-ROMs, including one on Bob Marley and another on Sting (this was still before the web, and these CD-ROMs allowed you to emulate a world inside your computer, but you were not linked anywhere outside of it). I was when I was working on the Sting CD-ROM when someone pulled me over to their computer. “Tiffany, you have to see this thing called the Web! There is something called a website, where people all over the world are connecting on how much they love Sting.” There it was! The moment I had been waiting for since writing up the UNITAS proposal back in the late eighties was finally here. It was 1995.
Soon after, I moved back to San Francisco and I would share news of this medium of the web to anyone who would listen. Most people didn’t know what it was yet. There was a vibrant, edgy, early community involved in the web, centering around South Park in San Francisco, including WIRED Magazine, the nascent Web Magazine and others . At the time, I was working as a contractor on an astronomy CD-ROM for a brilliant woman and soon best friend Maya Draisin. I was then hired by Web Magazine, an IDG publication, to build their website. I called it “Web Central Station,” and loved creating it. The concept was well received by the publisher, Greg Mason, who then told me, “We own the trademark Webby Awards, we have no budget, and what could you do with it?” I was like, “I’m an independent filmmaker, I know how to do things with no budget, and I love the web! I can definitely create The Webby Awards!” This was a perfect channel to bring together my passion for the web, my filmmaking, alternative perspective, and producing abilities to celebrate this new medium. The spirit of the first Webbys was to both honor this new medium and play with the concept of award shows with a tongue-in-cheek attitude about the spectacle of it all.
The first Webby Awards happened at Bimbo’s nightclub in San Francisco in Feb 1997, and was incredibly exciting. Sold-out crowd, international news. Mayor Willie Brown introduced the show. I made experimental short films to introduce the early categories, and I hired Cintra Wilson to MC. She introduced the five-word acceptance speech rule, and it was such a key part of the night, I kept it as a main part of the show ever since. The winners were the first to take on and create with this new medium. We were all at the epicenter of something that was soon going to change the world as we knew it.
In 1998, Web Magazine was sadly closed by IDG Publications. While the Webby Awards had been very successful in that first year, the magazine was both ahead of its time and not given enough time to grow. I proposed to the IDG Board of Directors that we establish she Webby Awards as our own entity. Since the editorial staff of the Web Magazine had been our judging body, I then co-founded the new judging body with Maya and Spencer Ante, calling it the International Academy of Digital Arts & Sciences. The Academy now has over 1,000 members and still serves as the Webby Awards' judging body.
The 2nd Annual Webbys happened in 1998 at the Exploratorium (when it was part of the Palace of Fine Arts), then in 1999 at the Herbst Theater, with the after-party at City Hall. By the year 2000, Vanity Fair called it the "It Award Show," The New York Times called it the "Oscars of the Web," and there was a peak event at the top of Nob Hill in San Francisco with Alan Cumming MC'ing the event. It was both the high and the beginning of the first dot-com crash. In 2001, the event was held at the San Francisco Opera House, and in 2002 at the Legion of Honor. That year, Maya Draisin and I experimented with a new format—both in response to the downturn and to empower others to host their own Webby Awards. We sent out kits with all the components needed to host a celebration.
Around that time, while I was making many short films about tech and society to introduce each year's Webby Awards, I created my first film outside of the Webbys in 2002, for Planned Parenthood, titled Life, Liberty & The Pursuit of Happiness. I made it while still running the Webby Awards. It was accepted into the Sundance Film Festival in 2003, and that was when I had a big aha moment—of returning to filmmaking and bringing together all that I had learned from the power of the web. I then brought in Recognition Media to acquire and run the Webby Awards. I stayed on for two more years. After nearly a decade devoting my time to building the Webby Awards, I wanted to return to filmmaking—this time combining everything I had learned from the web to make films about social issues, paired with digital tools to help people take action.
Today, I focus my time exclusively on my artwork, filmmaking, writing, and lecturing, and serve as director of my nonprofit film studio, Let It Ripple. My work merges the worlds of art, the Internet, and social change. My recent art exhibition was part of the Getty's PST ART: Art & Science Collide initiative in LA and traveling to San Francisco to the di Rosa Center for Contemporary Art opening Jan 20th, 2026. I am also still making films, the most recent ones, The Teen Brain about the neuroscience of adolescence and We Are Here about my moveable monument, Dendrofemonology: A Feminist History Tree Ring sculpture. I also authored a book called 24/6: Giving Up Screens One Day a Week to Get Back More Time, Creativity & Connection. After spending the first decade of my career being a big advocate for all things technology, when the iphone was invented and our data was being mined to keep us glued to the screens, I felt like it was taking over my brain. For 15 years now, I have practiced what my family calls "Tech Shabbats," where I turn off all screens for a day each week. The irony is not lost on me that while I still experiment all the time with new technology including having a strong AI component in my recent exhibition, that I am now a strong advocate for turning off all screens one day a week to get some perspective and hear what you thinking. Also my artwork today is both very much analog, rethinking the technology of tree ring dating, with dendrochronology, the original time machines.
The Webby Awards is presented by The International Academy of Digital Arts and Sciences in New York City every year. The 29th Annual Webby Awards will happen this spring in New York City. Check out the Webby Awards here.
Highlights
CNET asked Tiffany for a first-person account on her experience founding the Webbys with thoughts on how the world has changed for the web and filmmaking 20 years out. Read more.
Tiffany used to appear on ABC regularly as their "Internet Expert."