Wow this is an ancient thread but someone mentioned TMNT and that was by far the worst offender. Not because of the amount of diskettes but because it had the habit of reading (I'm guessing) 1 byte off of one disk then asking you to swap just to read 1 byte off the second disk and ask you to swap back.
I think there was 20+ disk changes every time you did something that required the game to load in the levels.
Which was pretty much anything. Loading the actual level was way more painful if I recall correctly, which I might not because it's been more than two decades and I only played it once. ;)
You'd just loaded a level and then accidentally walked over a sewer lid and the disk swapping started.
Then you had to climb out of the sewers and now you're up to like 40+ disk changes (not counting loading the level).
Then once you got out of the sewers you accidentally tapped the joystick in the wrong direction and rage quitting was a fact.
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If you had an extra disk drive this wasn't a problem but the game was still terribad.
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As for Monkey Island 2 that wasn't so bad even though it had 11 diskettes. Although 2 drives is recommended. If I recall it constantly needed disk 7(? It's been a long time) and one or two other disks depending on where you were.
It was fairly painless but of course it's a lot smoother with 3 disk drives (or 4) or a HDD.
I used to borrow my friends extra drives when playing games like that Until I got my first HDD and that sweet fast mem expansion.
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