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.