Comment by jeroenhd

I had to run a Linux binary compiled for Ubuntu 10.something a few years ago. I couldn't get the drivers to work properly in libvirt and getting the binary to run on modern Linux was practically impossible, even with 32 bit support installed.

The downside of dynamically linked binaries: every tool of medium complexity needs a close-enough version of a common library, and once those get upgraded, the tool dies.

Most statically compiled version should work with a compatible enough libc, but I haven't seen many old programs like that.

Wine, on the other hand, runs tools from the 90s just fine, as long as they're 32 bit.