OpenBSD on the Amiga in 95-96 or so.
Linux
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My first distro was Manjaro. It was really cool, but also I remember having some trouble getting things to work on it without super extensive troubleshooting.
Mandrake Linux 6.5. At the time I was drawn to it because they had a version that worked with the sims game.
It was around 2001 and I started by dual booting Windows with Red Hat, don't remember which version. Eventually I dropped Windows and dropped the dual boot and switched from Red Hat to Ubuntu.
RedHat here in the late 90s, back when you could still find yourself writing a "modeline."
Then Debian in the early 00s when apt was still a major discriminator. Finally, Ubuntu around 2008 just so I was running the same thing I was recommending to family members for ease of use. (At the time, Ubuntu sported the same ease of installation and hardware detection I'd found with Knoppix.)
Now on Xubuntu, but seriously eyeing a return to Debian.
RedHat in the mid-late 90s here too. It wasn't a great time for the linux desktop haha. I think I used afterstep or windowmaker back then. RPM hell was bad and hosed my system enough that Debian was like a savior with apt-get. Never really looked back from debian based systems since.
Ubuntu and Kali almost at the same time