August 24, 1995 – Microsoft rolled out a pretty major change to Windows user experience. It was big enough of a change, and caused enough of an impact in the computing world, that it warrants mentioning here. Windows 95's most noteworthy user interface changes, over its predecessors, were the addition of a taskbar and a menu-based application launcher (aka “The Start Button”). Not ground-breaking, but not poorly done either.
Horribly Painful Video: Jennifer Aniston and Matthew Perry starred in a half-hour long promotional video for Windows 95. Microsoft calls it “the first Cyber-Sitcom.” It might be, quite literally, the worst thing on the Internet. Go watch it. All of it.