At the "get out of Dodge" part of an Avernus campaign, the party had to split up to solve a puzzle to get to the top of a chained floating island. Everyone had their own last stand encounter (they knew it was coming and got to prepare). The Monk in the party just noped out and ran up a kilometer long chain watching all the mobs chasing him slowly fall away and die behind him as they chased him. Even without a nat 20 his dex was higher than a blazed giraffe.

The second lamest person in that party rode a nightmare to the top, after driving his hell machine off a cliff to get more air, he dipped, summoned his nightmare, and watched the miniboss plummet into hell lava with his death tractor. I made him roll for that shit after he announced what he wanted to do and he hit a nat 20. I didn't argue rules with the dice, it was too cool. He had crippled the things wings so it couldn't fly off. Absolute dick move on his part. All of it hilarious.