Crimson Skies. OMG many hours playing this trying to finish it, this was when games didn't hold your hand.
In The 1st Degree, FMVV game with multiple endings, choices used Apple Quicktime, now that was a pain on PC.
Star Trek A Final Unity
In The 1st Degree, FMVV game with multiple endings, choices used Apple Quicktime, now that was a pain on PC.
Star Trek A Final Unity

But yeah, there are so many editions and variations of those modern systems, it's often impossible to find the exact thing that prevents an older game from running. (This is one reason why my brief love affair with PC gaming ended with Win 98 and why I'm a console only player nowadays.)