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BonziBuddy,

BonziBuddy was a desktop virtual assistant created by Joe and Jay Bonzi. Upon a user's choice, it would share jokes and facts, manage downloads, sing songs, and talk, among other functions.
BonziBuddy was described as spyware and adware, and discontinued in 2004 after the company behind it faced lawsuits regarding the software and was ordered to pay fines. Bonzi's website remained open after the discontinuation of BonziBuddy, but was shut down at the end of 2008. On February 18, 2004, the Federal Trade Commission released a statement indicating that Bonzi Software, Inc. was ordered to pay $75,000 in fees, among other aspects, for violating the Children's Online Privacy Protection Act by collecting personal information from children under the age of 13 with BonziBuddy.