A long time ago I made a video on Clippy, the nearly universally hated paperclip from Microsoft Office. I figured now was a good time for an update.

Play the flash game here!
www.gamesbob.com/xtractpaperclip

And check out ClippyJS:
https://www.smore.com/clippy-js

Clips used in order of appearance:
The Kid's Guide to the Internet (0:54) -    • The Kids' Guide to the Internet  
12 old mac ads (1:13) -    • 12 Old mac ads  
Computer Chronicles UNIX (1:32) -    • Computer Chronicles - UNIX, 1985  
Peedy the Parrot: Interactive Music Assistant (1:35) - kurlander.net/DJ/Videos/PeedyVideo.shtml
Bill Gates' CES '95 Keynote Featuring Peedy the Parrot (2:56) - kurlander.net/DJ/Videos/PeedyCES95Video.shtml
X-Tract Paperclip game (6:29) -    • X-Tract Paperclip game  
Microsoft Office XP Ad 1/3 — Clippy Gets Clipped (6:33) -    • Microsoft Office XP Ad 1/3 — Clippy G...  
Delta Heavy - Ghost (7:42) -    • Delta Heavy - Ghost (Official Video)  
Microsoft Office Assistant - SNL (7:45) -    • Microsoft Office Assistant - SNL  
Agent Animated Characters Showcase-Bonzi
(9:16) -    • Agent Animated Characters Showcase-Bonzi  
Ribbon Hero 2-Clippy's Second Chance.wmv (9:41) -    • How To Play And Learn With Ribbon Her...  
Siri vs Cortana Groundhog Day (Commercial) (9:47) -    • Video  
Microsoft Goes Back to the Future (10:05) -    • Microsoft Goes Back to the Future