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Re:Valve Breaks the Shackles of Proton by innocenat on Tuesday January 22, 2019 @12:36PM (#18970242)
Funnily, when I was trying to get a 16-bit game to run, my final (and easiest) solution was to SSH to a linux machine, run it under wine, and do X tunneling back to my Windows system.

Works like charm.

Re:Valve Breaks the Shackles of Proton by AnIdiotOnTheNet on Tuesday January 22, 2019 @12:43PM (#18970315)
DOSBox with Win 3.11 usually works well for these cases.

From what I understand, Microsoft could have totally kept 16bit application compatibility in 64bit Windows, but didn't for some reason. Apparently someone out there even compiled a version of NTVDM that works on Win 10 64-bit using leaked code or something.