Microsoft Encarta 99
Encarta '99 was one of the most successful productivity/entertainment titles released by Microsoft. Intended as a flagship reference title with the launch of Windows 2000, Encarta brought multimedia to a new level. It was, for its time a complete interactive encyclopedia. Encarta was also the bane of schoolteachers throughout the world; with its ease of use, and wealth of easily searchable information, writing quick school reports became too easy. Encarta was so popular during the 90s that the title became a verb. Students would "Encarta" their homework the same way you would "Google" something today. Maybe too much information is a bad thing after all.
Encarta '99 also includes Mind Maze, a fantastic trivia program. If you are looking at this listing chances are you're familiar with the program and are ready to accept the challenge anew. Of course, you're older and wiser now, so a high score should be easy, right?