I’ll go first, I took my mom’s college textbooks which came with discs for a couple distros and failed to install RHEL before managing to get Fedora Core 4 working. The first desktop environment I used was KDE and despite trying out a few others over the years I always come back to plasma. Due to being like 12, I wanted to run my games on it, and man wine was not nearly as easy to use (or as good) as it is nowadays. So I switched back to windows until around 2015 or so when I spent the next few years trying to replace windows as much as I could. Once valve released proton, I switched fully and have t looked back, unless my still there windows partition tries to take over my computer when I restart it at least.
Maybe around 2006, I booted a live CD of Ubuntu and ran the 6 disc install of Unreal Tournament 2004 so that I could play UT with a friend who was staying over - the laptop was my mum’s, so I wasn’t allowed to install anything directly on it. UT2004 had a native Linux version on disc.
The install took until 4am and we played until the sun came up, absolute bliss getting it working.