My first OS was DOS 5.0, I switched to linux with Fedora core 6
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My first OS was Windows 98.
Linux distro was Ubuntu 6.0.
Atari 800 basic.
Gentoo was the first distro I used for any significant amount of time (college).
I had a Debian PC for a while, it was more of a project. IT work still revolved around Windows back then. Later I discovered Puppy Linux and ran that on a live USB. I encrypted the hard drive in my work laptop and never had to worry about anything making from the USB to my work data. Not a bad way to live, only had to carry around one laptop when I traveled for work.
First OS - DOS 5.0 First Linux - Knoppix
For Linux I started with Wubi to install Ubuntu 8.04 Hardy Heron. It installed Linux as a program in Windows and added some kind of hacky boot entry to boot into Ubuntu from your windows partition. Pretty cool, and I'm still pretty nostalgic for the GNOME 2 aesthetic with compiz effects from that time.
First OS: MS-DOS 5
First Linux (many years later): Yellow Dog on one of those dome-shaped iMacs with the PPC chips
Red Hat 7
mint->chromeOs->kali->windows->arch->openbsd->arch->nix