My DMs always do this but often without understanding the rules I'm taking advantage of, such as using fire or improvised weaponry. Like, I know how the game is meant to work, and it has rulings for what I'm attempting. I know what I'm trying to do is pretty weird; but I wouldn't attempt it if I didn't think I had a decent chance of rolling high enough to succeed.

Like once in D&D we were attacked by a giant in a forest. It was sprinting at us, so I asked if I had enough time to get a rope tied across two trees to act as a trip wire. The other players and our DM, to this day, still act like this was a silly and stupid thing to try; despite the fact it worked and got the fucker prone allowing us to kill him super easy.

The only thing I've done other than that they constantly joke about is the time we were playing Shadowrun and while attempting to sneak into a facility, I failed a roll and was seen by a janitor. So I shot him and hid the body; no witnesses. I don't care if it was a janitor for the McDonald's across the street. He saw me.