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 such as Microsoft’s annoying and judgmental paper clip assistant, Clippy (Are you old enough to remember Clippy? If not - good for you!). We can also thank Bob for the most hated font of all time: Comic Sans. THIS IS ALL YOUR FAULT, BOB.
Additional info:
Technologizer - A look back at a legendary software flop
Artsy.net - Bob and Clippy and more..