The 1999 Webby Awards were held on March 18, 1999, at the Herbst Theater (War memorial Opera House) 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.
Google founders Larry Page and Sergey Brin arrived wearing rollerblades and metallic capes, and remained in the opera hall lobby to grant interviews while most guests were watching the awards in the theater. The event was noted for the famous incident in which a representative of Jodi.org, which had won in the arts category, called the event participants "Ugly corporate sons-of-bitches" in his acceptance speech and tossed his trophy to the audience. The organizers asked PricewaterhouseCoopers to tabulate and ensure security for the "People's Voice" winners, chosen by online voting.