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Nat 20 on trying to convince the king to give you his throne? He’s amused and either hires you as a jester, or let’s you have a literal replica of his chair.
I see Nat 20’s on skillchecks as “something good happens, but if it’s impossible then the good thing might not be what you expected”
one time the dungeon master planned a big dungeon crawl and put a wall with a tiny hole to look through in it so we can see the boss before fighting it
one guy wanted to roll for breaking the wall with his sword. got a nat 20. we fought the boss early haha