Back when I first played Dark Messiah of Might and Magic, I spent way too much time atop some stairs and jump-kicking an orc down, who'd ragdoll down, get up then come back up, only to get another jump kick to the face. I spent several minutes laughing
When I was ~7 years old, I had a Nascar 94 demo for PC, my main mode of play was running the wrong way and crashing as hard as I could on another car, watching all the pieces flying was fun
I also wonder whether there's a "wrong" way to play dorf fortress, since I've tried a lot of stupid shit (it's only stupid if it doesn't work, so...)
Lastly, there's Skyrim with, uh, specific mods