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/clippyjs

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
XTract Paperclip game (6:29)    • XTract 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 ShowcaseBonzi
(9:16)    • Agent Animated Characters ShowcaseBonzi  
Ribbon Hero 2Clippy'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