Microsoft Bob
1995 - 1996
Microsoft's Bob was a cartoon interface designed to be easy to use for new computer users. But everyone hated poor Bob. Not only was the interface slower and more confusing than regular Windows, but the cutesy cartoons were annoying. Bob is one of Microsoft’s more embarrassing failures.
Although Bob didn’t survive, he left a legacy of irritation: the annoying and judgmental paperclip assistant, Clippy. We can also thank Bob for the most hated font of all time: Comic Sans.
Additional info:
Technologizer - A look back at a legendary software flop
Artsy.net - Bob and Clippy and more..