For me, my high bar that I have yet to beat, was the time I pivoted the running OS (ubuntu) into RAM over SSH so I could unmount and image the boot drive without rebooting and loading a live USB (Which would have required a ticket with my provider to enable IPMI)
That this worked when I did it in 2006:
wine ~/.wine/drive_c/Program\ Files/Warcraft\ III/Frozen\ Throne.exe -openglWine still feels like magic in 2025
Yes! It used to be so hit or miss with Wine, but I played WoW in it around the same time and it was crazy that it worked (at least most of the time).