I remember booting up Debian into an X11 session on a laptop with only 8 MB of RAM. (This would have been circa 2000, and I think I had to try a few different distros before finding one that worked. Also I don't think I did anything with it beyond Xterm and Xeyes.)
Me too, but I was able to do it around 1995-1996 :) Also remember Windows95 can boot with 4MB of RAM, and was decent with 12MB.
With either 4 MB or only a 386 CPU, it was definitely crippled, making an upgrade not worthwhile.