The Academy’s 2th Annual Interactive Achievement Awards were presented at a ceremony held in Las Vegas at the Hard Rock Hotel and Casino on May 13, 1999.

The presenters were Bruce Shelly (Senior Designer, Ensemble Studios), Peter Molyneux (Founder, Lionhead Studios), George Ailstair Sanger (“The Fat Man”), Bruno Campos (Jesse), Zachery Ty Bryan (Home Improvement), Gilman G. Louie (CCO, Hasbro Interactive), Ben Stein (Win Ben Stein’s Money), Tia and Tamera Mowry (Sister Sister), Chris Roberts (CEO/Producer, Digital Anvil), David Perry (President, Shiny Entertainment), Danica McKellar (The Wonder Years), David Gallagher (7th Heaven), Coolio, professional boxer Sugar Ray Leonard, Jez San (Argonaut Software), Thomas Galvin (Intel), and Nicolle Tom (The Nanny).

Zelda: Ocarina of Time, developed by Nintendo Co., Ltd. and published by Nintendo of America, won six awards, including overall Game of the Year and Console Game of the Year.  Half-Life, developed by Valve and published by Sierra Studios, won two awards, including PC Game of the Year.

Nintendo garnered six awards including the overall Interactive Title of the Year. Also earning multiple awards were The Academy presented Interactive Achievement Awards in 30 craft, console, computer and online categories. The Academy also inducted Sid Meier, founder of Firaxis, into the Academy's Hall of Fame. In keeping with Academy tradition, Shigeru Miyamoto, last year's Hall of Fame, returned to make the presentation.