Did BOB want out?
It's likely it isn't a real gun at all, and tampering with a gun to make it not fire is really easy, especially with the gun Cooper had in the glovebox. Also, remember how Cooper was surprised Ray ended up in jail for such a stupid thing and it was made a big deal of?
Ray and the Prison Warden could have been working together. If Ray is already friends with officials at the prison, Ray could have known Cooper was going to find out about his plan, and the entire facade of getting arrested, being in prison, and escaping, was all predicted by Ray (or perhaps Phillip Jeffries). The fact Cooper managed to escape might have been anticipated and desired. So when Ray said "Tricked you", he isn't talking specifically about the gun, I don't think, he could be talking about everything from the diner in Eps 1/2 up to Episode 8. Because Ray has managed to complete, as far as he is aware, the task of killing Coop.
I'm still wondering about Ray's ability to trick Mr. C from the beginning. I like your point about knowing that Cooper was going to figure it out and track him down and planning for that. I'm still not sure why he needed to download the layout of the prison (it was THAT prison wasn't it?) or how that helped him. Maybe before he got picked up for crashing and puking poison all over himself he was planning to hunt him down in his cell? Did Cooper know he was going to be taken to where Ray was? I thought they were insinuating in certain scenes that he could read minds and tell the future. Maybe that isn't right and the woodsmen are just his informants? This part isn't quite adding up for me yet.
A lot of things seem to go his way, but he did look pretty surprised about getting shot. I'll bet he's going to be pretty surprised to find out his evil roomie is gone too.
And I kind of think Bob wanted to escape too. He's feeling like the One Ring from LOTR to me. He uses his hosts, tricks them, and goes where he can do the most damage and get what he's after.
Not so sure BOB left Mr. C, since Ray said 'I saw something in him that might be the answer to all of this' as he was driving away and talking to Phillip Jeffries on a phone. Also, it didnt show BOB leave or even disconnected from Mr. C's body, just the 'BOB orb' appearing on the surface of Mr C's stomach.
Mr. C was getting power to come back to life from the 'spirit' of the crowd at the rock concert, which believed in his pain which allows him to continue on his rampage(the blood rubbing all over him to bring him back, heal him). So, Mr. C comes back to life right after the rock concert finishes. I think Ray was right when he said that the woodsmen were helping him, and these woodsmen could be the woodsmen connected to the crowd at the rock concert. The logic of something like: as long as people continue to believe in this sort of idea(pain as energy, sadomasochism, etc.), Mr. C and BOB will always be alive, no matter who or how many people are shot.
Never thought about how Ray set him up like that, but I will try to add to what you have said above. When Mr. C talked with his high tech surveillance equipment to someone he thought was Phillip Jeffries(maybe not, Mr. C thought, as if he is contact with red room, or changed this way), and during this conversation they were both talking about coordinates where reality would rupture and a 'spiritual' breakthrough in reality would occur, which is also the information Ray got from Hasting's secretary. And the guy Mr. C was talking to said that 'your going back to the black lodge tomorrow, etc.', showing that he has some knowledge of the coordinates and times of these manifestations., which means that he could have predicted when Mr. C would temporarily 'phase out' of reality and where it would happen(on the road, on the way to drug delivery, thus would be found by cops and put in south dakota prison), then plant Ray in that prison, lying in wait for Mr. C; remember how Mr. C said it doesnt make sense that Ray would be in prison for carrying guns, maybe he was in there to wait for Mr. C? Also, Ray was already in league with someone to kill Mr. C, was looking to backstab him the entire time, and wanted the money. Jeffries could have planted Ray in the prison, predicting Mr. C would have a way out to blackmail the warden(either to get himself out or get Ray released if he wasnt arrested), and that he would want Ray because Ray has the coordinates, sort of like laying the place for a trap for Mr. C. Jeffries could have then instructed Ray in ways to either blackmail the warden when he talks to Ray to release him, or have Ray tell the warden that he will kill Mr. C for him if he places a malfunctioning gun in the glove compartment and gives Ray a working gun......the 'trick' may have worked like this
And the guy Mr. C was talking to after he killed Darya with that equipment told him how he knew that Mr. C had met with Garland Briggs(then Mr. C says: 'how did you know that'); shows that this guy was following his movements and activity, had a 'tracking device'(cut in reality, 'spiritual gaze', etc.) on him and everything he was doing......so could predict his moves, etc., knew exactly his plans..., could thus set up the prison 'trick'....
Some amazing points in this thread, lots to think about! Total agreement about the NIN performance being a (barely disguised!) resurrection ritual. If Im reading Ray correctly, I think he was never in it for the money, he's a Blue Rose chaser in his own way. Mr C requesting him and Darya from the shack (which itself seemed at least Lodge-adjacent) already gave him a certain "spiritual status" from the outset, in my eyes... i was confused at their seeming-straightforwardness before!
Some amazing points in this thread, lots to think about! Total agreement about the NIN performance being a (barely disguised!) resurrection ritual.
I have to change the argument I made before about the performance being a resurrection ritual and what I said about the role of the woodsmen in relation to the NIN performance; and I just got an idea(which connects my old ideas to this) from reading that interview with MacLaughlin. I think it is a resurrection ritual, but one that is meant to be the death of BOB, a death he and the woodsmen try to hide from which allows him to go on living, and this song is reminding him he is dead; and the song could be seen as an atomic blast(shes gone) which creates pain-fire from which BOB and woodsmen emerge....
Its not that the song directly resurrects BOB, the song is just stating 'shes dead'/lauras dead which was the atomic blast that overturned the illusions about twin peaks, brutally exposing its rotting underside, an atomic blast which upsets all consistent reality. Out of this 'fire' of the blast emerges BOB and the woodsmen, and they are burnt, dark grease/oil, burns on the skin, etc. BOB wants garmanbozia/pain, they turn the pain/fire from the blast which should kill them into a way to hang on after they are dead(as if they are saying, you are trying to kill me, I feel pain, I refuse to recognize I am dead and enjoy the pain, to just keep going on after death and resist the registration of their own death into reality). BOB and the burnt woodsmen, they all enjoy the pain, which is why the rubbing of blood by the help of the woodsmen heals Mr. C and brings him back to life, pain becomes the source of life. As if someone was searching for Laura as an object of desire, found out she was a brutal sadomasochist inflicting pain and manipulating those who cared about her, but instead of treating Laura as a tragic dead beauty killed by the community, they still desire her as the ultimate object, refuse to accept she is gone, that shes dead(NIN song), and are forced to enjoy in pain.
This is the relation of BOB to the sleeping giant and the Laura atom: giant, old law of consistent reality is gone and dead(example: Twin peaks as the ideal community that people like old agent cooper all believed in torn apart by the revelation of Laura's tragedy), now BOB and woodsmen arise because they are hiding from Laura being dead, they still need her and pretend beautiful. BOB always needs and is chasing Laura in a brutal painful way, the pain and death doesnt matter, must keep Laura alive. The other way to react to the atomic blast/laura's body is like James, the other side of BOB, the sleeping giant that refused to even look at the blast, always pretended Laura never had problems and that she was alright, the ideal homecoming queen etc., no matter what she tried to tell him, etc. White and black work together here, support each other, white on surface black inside, white hides the black from being revealed, where it would truly be dead and problems would have to be dealt with and solved; and this is why the song is actually trying to kill Mr. C/BOB, who survives never the less, like surviving in the wake of an atomic blast, giving birth to 'Laura'/mother at the sleeping giant's(and woodsmen's) expense. And this is why Laura is the brutal mother in control, free to manipulate and lead people on, ruin people like she was ruined out of revenge; seduced old agent cooper during his first dream, when 'the arm' played matchmaker for the two and he woke up gitty, snapping his fingers, allowing him to later be trapped by Laura for 25 years after she kisses him and whispers etc.....
Also this logic of BOB/Mr. C/Woodsmen explains the 'lost highway' reference, when after getting rid of the tracking devices, Mr. C tells Ray to 'get off of this highway' and they go down the dark road; and the shootout scene is reminiscent of the movie as well when Pullman shoots the big mafia guy. Lost highway is in one way this enjoying in pain, trying to get rid of the atomic blast/lauras death(coming back to life after death, becoming a potent young kid instead of a psychotic cuckold dead in jail, being BOB, enjoying pain) Atomic blast kills reality and causing pain, the main highway is lost, and forced onto another highway in pain, your death, the end of the line, which BOB/Mr. C hide from, thus Mr. C is resurrected; Lost Highway, lost your life...last little road before death, holding onto power after your time in history is over. In the movie lost highway, the guy tries to hide from the fact that his wife is cheating on him and humiliating him, then tries to get rid of all the obstacles which prevent full union with the woman(mafia guy, etc.), to avoid the fact that the obstacle cannot be done away with, that he can never 'fully have the woman', that it is just an 'atomic blast' at the middle and the only thing there is is how the man and woman tried to work around this failing and create something(which in this case is brutal abuse, nothing there). This is the logic of BOB, when he fully wants to be Laura, wants to fully be inside her, etc.....
'tracking devices' cut right through the person, see a weakness(like ray could be the tracking device symbol on the bottom, like the red and white colored criminals throughout the series) these devices see their inner failure(like the guy threatening Mr. C to return to black lodge), expose it that they are dead(like that evil guy in lost highway who tells pullman at the party that he is in his house right now, etc.), so this is why when Mr. C gets rid of them, then end up on the lost highway, the normal highway is lost, old reality/twin peaks died when lauras corpse was discovered, now stuck on brutal side path that only ends in dead: Mr. C/BOB is just trying to avoid the atomic blast/ that 'shes gone'....