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Only the oldest millenials did. When the youngest were born, the internet and Windows 95 were readily available and they were in middle school when the iPhone came out.
Yea, I’m a millenial, and I remember mostly only interacting with old Macintosh LCs in elementary school, and then Windows 95 and up after that. My uncle had an old Tandy computer running DOS, that I remember at least learning how to run a game on, but by the time I was interacting with a computer, regularly, Windows 95 and AOL were the most common thing.
We did have some DOS games on CD during the Windows 95/98 era, though. Lemmings always ran better if you dropped down to DOS and ran it from there instead of trying to run it through Windows, for instance.