Monk seemed to have an attitude where he could make a mistake in the very first bar on a record date and just keep going regardless.
Sam Rivers screws up the out head pretty badly on Cyclic Episode. Those 1960s guys had such a relaxed attitude about mistakes. I quite admire that, actually.
I recently recorded an EP and it made me very aware of the little mistakes that end up on a record, and since then I've been hearing tiny flaws in records I'd listened to dozens of times before without noticing anything. Irish stuff in particular, nothing you would be familiar with.
Of course my EP has plenty of little mistakes, from phrases that start just a milisecond too early/late, to actual fluffed notes.