Clippy
The animated paperclip assistant from Microsoft Office, mentioned humorously as a desirable return and a symbol of past software features.
Common Themes
Videos Mentioning Clippy

Design for Startups by Garry Tan (Part 1)
Y Combinator
An anthropomorphic AI assistant from Microsoft Office, mentioned as an example of interface elements that can make interactions feel more human.

Jaron Lanier: Virtual Reality, Social Media & the Future of Humans and AI | Lex Fridman Podcast #218
Lex Fridman
Microsoft's animated paperclip assistant, which Lanier suggests bringing back, but the host notes it 'pronounced the myth of AI'.

Kate Darling: Social Robotics | Lex Fridman Podcast #98
Lex Fridman
Microsoft's former writing assistant, described by the host as a brave attempt at a personality.

Kevin Scott: Microsoft CTO | Lex Fridman Podcast #30
Lex Fridman
An AI assistant from older versions of Microsoft Office, humorously mentioned in the context of potential future AI assistants in Office products.

Rosalind Picard: Affective Computing, Emotion, Privacy, and Health | Lex Fridman Podcast #24
Lex Fridman
An animated office assistant from Microsoft Word (Word 95/98) that provided help. It is used as an example of emotionally unintelligent AI.

Lee Cronin: Controversial Nature Paper on Evolution of Life and Universe | Lex Fridman Podcast #404
Lex Fridman
The animated paperclip assistant from Microsoft Office, mentioned humorously as a desirable return and a symbol of past software features.

Kate Darling: Social Robots, Ethics, Privacy and the Future of MIT | Lex Fridman Podcast #329
Lex Fridman
A virtual assistant from Microsoft Office, described as an annoying social agent that people loved to hate, demonstrating how people treat virtual characters as social beings.