Stop Making Sense, Nathan For You: Finding Frances, Paris is Burning, Minding the Gap, Kingdom of Dreams and Madness, You Cannot Kill David Arquette, Horror Noire, Close-up (kind of a documentary, kind of not. It is my favorite of all the movies I listed though). A good variety of favorites.
I like this idea a lot. I feel like RALRO has done a lot within the world building of TBC alone. Especially with his stuff with Jebediah. Gedo being a product of that gives good reason for her to be a constant presence in Hell with Billy too. It also would make sense that Jazzy and Suave also added that extra layer of "punishment" as well, to help him be more mature. Considering it's implied he was swayed by Jebediah to try and kill his brothers. Gedo being a reminder for Billy on what he has done to his brother in every timeline is something that probably weighs a lot on him too
now this is a great scenario. I could see all 5 of them being crunched in the same hotel room because Yaemon claims he cannot pay them to stay in separate rooms. He'd the probably tote them around as "The Greatest 5 Workers Ever Assembled" to each and every investor. For sure, the 5 will escape and just hang out in some backroom somewhere chatting it up and taking hits of nicotine.