BonziBuddy
A purple gorilla who lived on your desktop, told you jokes, and quietly went through your business. BonziBuddy is the friendliest thing ever classified as adware by two antivirus companies. Half the internet remembers installing it on purpose.
BonziBuddy was released in 1999 by Bonzi Software, created by Joe and Jay Bonzi. It ran on Microsoft Agent — the same animated-assistant technology built for the Office Assistant, which is to say Clippy's engine wearing a different costume. The FTC's own description is hard to improve on: free downloadable software that put an interactive, animated purple gorilla on your computer to interact with you while you were online, "providing shopping advice, jokes, and trivia."
The gorilla wasn't there at the start. The original BonziBuddy used Peedy, a green parrot borrowed from Microsoft's stock Agent characters; Bonzi the purple gorilla arrived in a May 2000 update, about a year in. The thing everyone pictures is the second draft.
Then the bills came. In 2002 Consumer Reports Web Watch labelled BonziBuddy spyware, and Trend Micro and Symantec both classified it as adware. A class action accusing Bonzi of running banner ads that deceptively imitated Windows system alerts — the fake close button everyone clicked — settled on 27 May 2003. Separately, in February 2004, Bonzi Software paid a $75,000 civil penalty to settle FTC charges that it had collected personal information from children without parental consent, in violation of COPPA; the FTC noted it was the first COPPA case to go after an online service's data collection through a software product rather than a website. Bonzi discontinued the software in 2004, left it downloadable through 2005, and shut the Bonzi.com portal in late 2008.
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