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I actually had more success getting old windows games to run in modern linux with wine than in modern windows.
“Just run it in compatibility mode bro, it’s fine bro!!!”
My computer screen suddenly turns 640x480, flickers 5 times, then crashes because -checks notes- my graphics drivers are too new.
Yes this has actually happened to me. No I can’t remember with what game (I wanna say Deadly Premonition).