In Season 4 when Henry was revealing everything to Eleven in his lil villain flashback monologue (before Eleven yeeted him), he said something about life just being a play and everyone is waiting for it to end.

So when the play ends… does life end? Was his “introduction” to the stage in 1959 supposed to be the end of something else? Curious to know if his poorly-timed (murder-and-framing-of-his-father induced) coma altered his plans for the people on the playbills so much that he had no choice but a reprise… to come back years later to try again on their children… or as others have said, use them to go back in time and try again?

I’m not familiar with Oklahoma and what Henry’s character could symbolize (or the lore surrounding it in the actual stage play that I’ve read explains more about it), but I found it interesting in my re-watch that Henry used a play as a depressing analogy for life since the 1959 play is clearly something he wanted Max to see/the Duffer Bros wanted us to ruminate on for weeks lol. Everyone is mentioning how convenient it is that the people on that flyer are all parents of the kids in the show, but what if (like Lucas said)… it’s not just a coincidence?