If you’ve been using Microsoft Word for many years, perhaps you remember a time when a cartoon paperclip would sit on your page, offering up advice about how to do things in the program. This was Clippy, and apparently no one ever liked him, including early focus groups. Microsoft didn’t listen to them, however, so he went on to be loathed by a much wider audience.
From The Atlantic:
Clippy is famous for being one of the worst user interfaces ever deployed to the mass public. He stopped users to ask them if they needed help with basic tasks, like writing a letter or making a spreadsheet. As the Microsoft employee Chris Pratley has written, Clippy was “optimized for first use”: amusing the first time you encountered him, and frustrating after that. He was a puppet who only knew one script and kept repeating it, at you, throughout the workday.