Wordperfect was *the* standard word processor in the late 80's/early 90's. When Microsoft's Word 2.0 came out, with a beautiful GUI and no more finger-contorting F-key combos which required a chart to use, it **blew away** Wordperfect. Excel's inline graphs, expression helper, and crazy-easy cell formatting **blew away** Quattro Pro. Access' drag and drop table linking, virtually automatic query generation, and included example dbs and help system **blew away** Paradox/Dbase. It was a revolution that Microsoft ushered in. For most laypeople, it wasn't just cool, it was near magic. First they made "cool" killer apps when others were stagnant and relying upon their entrenched position to keep up sales. And then they put in place anti-competitive agreements with OEMs to make sure they kept their position.
In the late 90's, Microsoft was no longer cool for end users, but for developers and their associated sales force, they sure were. Devs were EXCITED to use MS's development tools and languages (VB/C++/Interdev/etc.). It was cheap to get started, plus there were a ton of resources for cheap training. SQL Server had easy hooks into all of the MS stuff, and watching a five minute demo on linking a SQL Server db to your web app was powerful. A new generation of IT admins preferred Windows NT's GUI to command line Solaris/Irix/AIX/etc. This was all backed by the ease of becoming a Microsoft partner, which would mean a steady flow of sales leads to your shop. For better or worse, their technologies revolutionized a whole generation of developers who thought MS was cool. First they had cool tools when others were stagnant and relying upon their entrenched position to keep up sales. Then they used shady, anti-competitive tactics to keep that position.
All I'm saying is that they were perceived as cool at one point. I'm also saying that I'm glad that era looks to be over.