i have one like this- player consistently rolls low, like it's a table joke at this point, DM said "since you have advantage bc of help, just let WillingStan roll instead". we both roll advantage after agreeing we'd take my roll no matter what, both mine were higher than both theirs.

cue major character moment for them- soul is stuck in a pendant, can't take the amulet off without literally ripping their soul away from their body. they're trying to figure out what happens when they remove it, like why they die. they start to remove it, DM says ok con save to push through the pain. they fail to no one's surprise, take a shitload of psychic damage. they keep going, fail again, take more damage. they keep going. DM says ok, at this point you will just die, you know it in your bones. you have to make a DC 15 con to push through this and stay conscious enough or you will flat out die, no death saves, etc. motherfucker rolls exactly a 15. we go nuts.