The 1999 Webby Awards were held on March 18, 1999, at the Herbst Theater in San Francisco, California. IDG, which still owned the awards organization, continued to retain Tiffany Shlain to produce the awards even though the magazine division she had been working for had been shut down. Mayor Rudy Giuliani had lobbied to move the ceremony to New York City, but San Francisco Mayor Willie Brown interceded with Schlain by promising the city's support, including hosting a post-award party at the newly remodeled City Hall.
The 1997 Webby Awards were the first of the annual Webby Awards, and also the first-ever nationally televised awards ceremony devoted to the Internet. 700 people attended the event on March 6, 1997, at Bimbo's Night Club in San Francisco, California.
Held in San Francisco's Masonic Center for a crowd of 3,000 invited guests, the 2000 Webby Awards were widely considered the peak of the Webby Awards and a watershed of dot-com party culture. The event took place May 11, 2000, shortly before many of the event's perennial nominees and participants suffered business failures in the dot com crash.
The 2001 Webby Awards were held in San Francisco at the War Memorial Opera House on July 18, 2001, hosted by Alan Cumming. The Lifetime Achievement Award, which debuted this year, went to Ray Tomlinson and Douglas Engelbart. It was the first awards held after the dot-com crash; as a result, they were smaller and quieter than in years past. The organization hired agency Diesel Design to create three ancillary sites to their main one for the 2001 ceremony, one site dedicated to award nominees, an RSVP site for guests, and a site for the winners. The agency also created print and online ads for the awards show, as well as interior signage, posters, and invitations.
The ninth annual 2005 Webby Awards ceremony was held in New York City on June 8, 2005. It was hosted by comedian Rob Corddry, and judging took place covering 4,300 sites from more than 40 countries by the International Academy of Digital Arts and Sciences. Al Gore was awarded a lifetime achievement award and for his five-word acceptance speech he delivered the frequently-cited line, "Please don't recount this vote" – a reference to the 2000 Florida election recount.
The 12th annual 2008 Webby Awards were held on June 10, 2008 and emceed by SNL head writer Seth Meyers and help at Cipriani, a massive banquet hall in Manhattan's financial district. The Webby Film and Video Awards were held on June 9 at Skirball Center for the Performing Arts and were hosted by Judah Friedlander. The awards were judged by the International Academy of Digital Arts and Sciences, and winners were selected from over 10,000 entries. Lorne Michaels was honored with a lifetime achievement award.
The 11th annual 2007 Webby Awards were held in New York City on June 3, 2007. They were hosted by comedian Rob Corddry and were judged by the International Academy of Digital Arts and Sciences. The ceremony saw 8,000 entries from over 60 countries and all 50 United States. Lifetime achievement awards were given to David Bowie and YouTube founders Chad Hurley and Steve Chen. This award ceremony for the first time introduced category awards beyond Websites in the three new super-categories: Interactive Advertising, Mobile & Apps, and Online Film & Video.
The 10th annual 2006 Webby Awards were held on June 12, 2006, at the Cipriani Hotel in New York City and were hosted by the comedian Jon Stewart. Judging was provided by the 500-person International Academy of Digital Arts and Sciences, and winners were selected from among 5,500 entries from around 40 countries worldwide. This award ceremony saw the creation of a new award category, "Best Viral Video".
The 7th Annual Webby Awards were held in San Francisco, California on June 5, 2003. Due to budget cutbacks made in response to the 2002 Internet bubble, the decision was made to hold this year's ceremony partially online. This would be the last year that the Webbys would be presented in California prior to their relocation in New York City. For this award ceremony, the business category was expanded with the addition of a new award for "Best Online Businesses." This award would be presented for "sites that excel at achieving fundamental business goals such as increasing sales lead generation or enhancing customer loyalty and retention, marketplace impact and innovation."
The 8th Annual Webby Awards was held on May 12, 2004. Due to cutbacks in the Webby event budget resulting from the 2002 Internet bubble, the decision was made to hold this year's ceremony entirely online. Judging was provided by the 480-person International Academy of Digital Arts and Sciences.
The 6th Annual Webby Awards was held on June 21, 2002, at San Francisco's Legion of Honor auditorium. It was presented by the International Academy of Digital Arts and Sciences and was hosted by Tiffany Shlain, the Webby Awards' founder, and Maya Draisin. Coming on the heels of the dot-com bubble, a 2002 Internet bubble forced cutbacks in the event budget for this ceremony as well.
The 15th annual 2011 Webby Awards were held on June 13, 2011 in New York City. The show was hosted by Lisa Kudrow and was streamed live via Facebook, The Huffington Post and Funny or Die. The Webby for lifetime achievement was awarded to former Motorola executive, Martin Cooper.
The 13th annual 2009 Webby Awards were held in New York City on June 8, 2009. They were hosted by SNL head writer Seth Meyers, and the lifetime achievement award was given to Jimmy Fallon. The awards were judged by the 650-person International Academy of Digital Arts and Sciences, and winners were selected from among nearly 10,000 entries from 60 countries and all 50 United States. Voting by the public was available prior to April 30, and over 500,000 votes were cast. The awards ceremony was made available for viewers via the official Webby YouTube channel.
The 14th annual 2010 Webby Awards were held in New York City on June 14, 2010. They were hosted by comedian B. J. Novak, and the lifetime achievement award was given to Vinton Cerf. The awards were judged by the International Academy of Digital Arts and Sciences.
The 16th annual Webby Awards for 2012 were held at the Hammerstein Ballroom in New York City on May 21, 2012, and hosted by comedian Patton Oswalt. Winners were selected from among roughly 10,000 entries and voting by the public for the People's Choice Award was available prior to April 26. The awards ceremony was streamed live in HD on its website.
The 17th annual Webby Awards for 2013 was held at the Hammerstein Ballroom in New York City on May 22, 2013, hosted by comedian Patton Oswalt. It was streamed live at www.webbyawards.com.
The 19th annual Webby Awards for 2015 was held at Cipriani Wall Street in New York City on May 19, 2015, which was hosted by comedian and actor Hannibal Buress. The awards ceremony was streamed live at the Webby Awards webpage. Judges from the International Academy of Digital Arts and Sciences picked the over one hundred winners, which may or may not match the people's choice.
The 20th annual Webby Awards for 2016 was held at Cipriani Wall Street in New York City on May 16, 2016, which was hosted by comedian and actor Nick Offerman. The awards ceremony was streamed live on the Webby Awards website. Judges from the International Academy of Digital Arts and Sciences picked the over one hundred winners, which may or may not match the people's choice. The Webby for Lifetime Achievement was awarded to The Onion, having earned over 39 Webbys for its humor over the past 20 years.
The 23rd annual Webby Awards were held at Cipriani Wall Street in New York City on May 14, 2018, which was hosted by comedian and writer Amber Ruffin. The Webby Awards have been dubbed the "internet's highest honor" and, in 2018, received over 13,000 entries from 70 countries, with 10% receiving nominations.
