A character gets into a contest of some sort with The Grim Reaper, Satan, or some other supernatural entity, usually with some dire consequence if the human loses. This is Older Than Feudalism, with examples dating back to Greek myths of the 5th century BCE - Apollo had at least one musical duel, the Muses had another musical contest, and Athena had a weaving contest with Arachne (the details vary between different versions, but the end result is that Arachne ended up being turned into a spider). Compare Did You Just Scam Cthulhu?. Examples with Chess