N.B.: AFAIK, running 16-/32-bit Windows software under open-source Wine on Mac OS, as seen here, is no longer possible on 10.15+ due to Apple dropping support for 32-bit software; commercial CrossOver[2] supports 32-bit software on newer Mac OS versions (and I assume 16-bit, though I haven't tested it).
[1] https://jasomill.at/Fallout2.mp4
N.B.: AFAIK, running 16-/32-bit Windows software under open-source Wine on Mac OS, as seen here, is no longer possible on 10.15+ due to Apple dropping support for 32-bit software; commercial CrossOver[2] supports 32-bit software on newer Mac OS versions (and I assume 16-bit, though I haven't tested it).
[2] https://www.codeweavers.com/crossover