- BeOS was JFK. – They both got gunned down before we could possibly see any downsides to them.
- MS-DOS 1.0 was Herbert Hoover, aloof to the problems of the common man but friend of the engineer in all of us. Also discovered Transformers.
- Mac OS 7-8-9, all Franklin Roosevelt, very competent, lead us through difficult times, but left a legacy of programs which have become quite a mixed bag.
- Windows 3.1, Dwight Eisenhower, amiable enough, competent, but leaving historians (and many contemporaries) very wanting.
- Windows 95 thru ME, Lyndon Johnson, one of the boys, very able at getting things done, but in the end a disaster, rightfully ceding his throne.
- Windows NT, Richard Nixon, the archetypal back-room politician, ruthless, and ultimately brought down by little faults, but many believe he was a great president and did much to modernize the Republican Party.
- Windows XP, Ronald Reagan, everybody who hates him never met him, he could charm anyone, the Great Communicator. Bought Iranian weapons for contras with drug money.
- Mac OS X, Bill Clinton, cheerful and smart, if not the most productive. Known for his speeches.
- Vista, George W. Bush, elected because of his name, even though the prior iteration wasn’t especially respected or well-liked. Introduced instability and performance issues, all in the name of “security”. Many of the corporate interests who promoted him early on are having second thoughts.
Taken from this discussion on Slashdot. Credit to cmowire and iluvcapra.