Mr Monkey Merch
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Description: If you’re old enough to remember BonziBuddy, you may recall that he was one of the web's early virtual assistants (think Clippy, but for browsing the web). BonziBuddy's virtual desktop assistant featured an on-screen avatar of a talking purple gorilla that could interact with its users and run simple utility services like text-to-speech and finding online shopping deals. Released in 1999, the application was actually pretty impressive for the time, and garnered notoriety for its early forays into what we now know as targeted advertising. This early personalizing of ad content was more akin to spyware, adware, and scareware than anything, so it's not surprising that the developer faced several lawsuits and fines from the FTC.
