Clippy

The Office Assistant was an intelligent user interface for Microsoft Office that assisted users by way of an interactive animated character, which interfaced with the Office help content. It was included in Microsoft Office for Windows (versions 97 to 2003), in Microsoft Publisher (versions 98 to 2003), and Microsoft Office for Mac (versions 98 to 2004).

The default assistant in the English Windows version was named Clippit (though Clippy is a common nickname), after a paperclip. The character was designed by Kevan J. Atteberry. Clippit was the default and by far the most notable Assistant (partly because in many cases the setup CD was required to install the other assistants), which also led to it being called simply the Microsoft Paperclip. The original Clippit in Office 97 was given a new look in Office 2000.

The feature drew a strongly negative response from many users. Microsoft turned off the feature by default in Office XP, acknowledging its unpopularity in an ad campaign spoofing Clippy. The feature was removed altogether in Office 2007 and Office 2008 for Mac, as it continued to draw criticism from even Microsoft employees.

The default assistant Clippit has been heavily mocked in popular culture, being parodied, appearing in memes, and even being made fun of by Microsoft themselves from 2001 onwards.

According to Alan Cooper, the "Father of Visual Basic," the concept of Clippit was based on a "tragic misunderstanding" of research conducted at Stanford University, showing that the same part of the brain in use while using a mouse or keyboard was also responsible for emotional reactions while interacting with other human beings and thus is the reason people yell at their computer monitors.Microsoft concluded that if humans reacted to computers the same way they react to other humans, it would be beneficial to include a human-like face in their software As people already related to computers directly as they do with humans, the added human-like face emerged as an annoying interloper distracting the user from the primary conversation.

...
Wikipedia