Launch date: 1997

Fatal flaw(s): Intrusive, privacy risk

Before Facebook's big privacy scare, Comet Systems' Comet Cursor made front-page news with its sneaky-ass ways. Essentially software than can customize your computer's mouse cursor, Comet Systems partnered with a number of big web sites like Warner Bros., AT&T, and Energizer, designing custom cursors that would activate when customers browsed over to their sites. It was crazy annoying and drained your system's processing power, but that wasn't the bad part. That came when people discovered that the software was assigning every user an ID number and sending information on the sites they were visiting and the other software they had installed on their computers back to its headquarters. After an investigation, the Comet Cursor, which was downloaded over 200 million times thanks to loopholes in Internet Explorer, was ruled to be spyware.