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Windows is very epic, but they did break compatibility a few times: the new driver model since Windows 7 (?) for example.

The Web probably has a longer history of not breaking things, but also has a smaller feature set to keep track of than Windows.

All in all, very hard to compare. But both undoubtedly epic.

The new driver model is Vista-era, I think.

For all the (often deserved) hate Windows gets, in particular the user space API’s, I still find the chaos incredibly exciting and an invitation to hack together all sorts of strange things in strange manners. I’m sometimes surprised by the levels of backwards compatibility and the “obsolete” technologies that still work fine.

You might well be right! Would be fun to see them go head-to-head over the title.

The success of Windows to maintain backwards comparability is probably some of the inspiration for the people working on JS. Windows has demonstrated that it's possible to maintain backwards compatibility for decades.

It's not easy, and it certainly leads to annoying platform quirks, but it is possible.