Categories include websites, advertising and media, online film and video, mobile sites and apps, and social.

[8] The winners of the First Annual Webby Awards in 1995 were presented by John Brancato and Michael Ferris, writers for Columbia Pictures.

The first Webby Awards were produced by Kay Dangaard at the Hollywood Roosevelt Hotel as a nod to the first site of the Academy of Motion Picture Arts and Sciences (Oscars).

The modern Webby Awards were co-founded by Tiffany Shlain, a filmmaker,[11] when she was hired by The Web Magazine to re-establish them,[12] and were first held in San Francisco in 1997.

[15][16] The International Academy of Digital Arts and Sciences, which selects the winners of The Webby Awards, was established in 1998 by co-founders Tiffany Shlain, Spencer Ante and Maya Draisin.

[17] Members of the Academy include Kevin Spacey, Grimes, Questlove, Internet inventor Vint Cerf, Instagram’s Head of Fashion Partnerships Eva Chen, comedian Jimmy Kimmel, Twitter founder Biz Stone, Vice Media co-founder and CEO Shane Smith, Tumblr’s David Karp, Director of Harvard's Berkman Klein Center for Internet & Society Susan P. Crawford, Refinery29’s Executive Creative Director Piera Gelardi, and CEO and co-founder of Gimlet Media Alex Blumberg.

[26] Executive Academy Members with category-specific expertise evaluate the shortlisted entries based on the appropriate Website, Advertising & Media, Online Film & Video, Mobile Sites & Apps, and Social category criteria, and cast ballots to determine Webby Honorees, Nominees and Webby Winners.

In 2005 when accepting his Lifetime Achievement Award, former Vice President Al Gore's speech was "Please don't recount this vote."

"[34] In 2013, the creator of the Graphics Interchange Format (GIF), Steve Wilhite, accepted his Webby and delivered his now famous five-word speech, "It's pronounced 'Jif' not 'Gif'.

"[39] In response, Webby Awards executive director David-Michel Davies told the Wall Street Journal that entry fees “provide the best and most sustainable model for ensuring that our judging process remains consistent and rigorous and is not dependent on things like sponsorships that can fluctuate from year to year.”[38] In 2021, the Webby organization started a new line of awards, the Anthem Awards, to honor the purpose and mission-driven work of people, companies and organizations worldwide.