ProbieTim or it became a turning point in the saga after the fact. Note: Tolkien confessed that he didn't plan his story ahead of time, he let it unfold as he wrote it (because that's pretty much how he wrote The Hobbit - as an ongoing bedtime story for his children). I can imagine Tolkien's DnD group:
Bilbo's player wants to retire his old character and tries to sneakily pass on the most useful magic item in the game to his new character, Frodo - that's when DM Tolkien decides to make it cursed.
Aragorn's player complains that it's not fair that the Frodo Player get to keep his previous characters magic ring when his previous character, Thorin, had a cool sword. DM Tolkien sighs and says "fine, you can have a cool magic sword ... but you're too low a level for it at the moment so it's currently broken and you can only get it mended when you reach a high enough level"
Gandalf's player gets pretty pissed about the Balrog encounter because he hasn't been able to advance in level since DM Tolkien made his characters mentor, Saruman, evil. DM Tolkien realises that was a pretty dick move: "tell you what I'll let you call on a divine intervention, the chances are slim but you never know". Player rolls a 01 - "right so as you plummet into the abyss your God hears your plea, he'll bring you back BUT you gotta be really faithful to that God now and basically you do that God's work on MiddleEarth".
Gandalf's player: "cool, but what about training up a few levels, I've all this XP and no mentor". DM Tolkien: "I told you about Galdriel in Lothorien as a new mentor?". Gandalf Player "No, you didn't, you said the rumours were that bad shit happens in Lothorien and to stay away", Tolkien "no, no that's the rumour I passed you a note saying it wasn't true". Aragorn's Player "ummm I think you passed it to me by accident, I did wonder why the fuck you were telling me that". Tolkien "okie, cool so Gandalf will be out of action for few weeks while he trains up - so I'll have him catch up with the rest of you later".
Boromir's Player decides to seize The Ring, Tolkien has also just checked for wandering monsters - a passing Orc War Band . . . isn't that how all great RPG adventures are made?