I remember watching MD when at uni and thinking WTF, only really got back into it recently, and with the help of Goggle and numerous theories, have tried to piece bits together
I wanted to post my thoughts on the Cowboy, this character has been 'bothering' me and I have read a number of theories as to his role, im gonna offer an alternative (that at least I havent read before)
The cowboy for me offers the last chance.
When he is menacing Adam at the Coral he is basically saying this is your last chance to do right, reopen and cast the girl
When he speaks of seeing me once if you do good and twice if you do bad, he is not talking to Adam, it is Diane's get our card, he is talking to Diane
I mean lets analyse this, if he was talking to Adam, what would he do on the first meet if Adam did well, shake his hand and say well done - hardly seems the type.
And if Adam does bad then what would he do on the first meet ? well I dont think there would be a second meet if Adam does bad.
No he is talking to Diane and saying im offering you a way out now.
Let me continue
I believe that Camilla was killed by the hitman in real life whilst Diane was still dreaming (Makes sense as she kind of dreams she hopes it doesn't happen)- whatever time frame that was, but up until the cowboy is introduced in the dream, in reality Camilla is still alive.
So I feel if Diana wakes up there and then she still has time to call of the hit, and she will see the cowboy just one more time as she exits the dream world - does good.
But no she carries on with the dream , so when exactly in the dream does Camilla die, well this bit bothered me as there is no real reference to time, but I feel it is in CLub Silencio, either when She has convulsions or when the Spanish 'Roy Orbison' drops down dead.
Then it is the time for the dream to end.
The fact the blue key is there when she wakes up and she is surprised to see it says that it is a distinct possibility it wasn't there when she went to sleep.
Ok so thats one cowboy sighting what about the second.
Well the second is because when she sees that key and realizes she has 'done bad' she thinks back to where it all went wrong - the masturbation scene on the sofa and the sudden switch to answering the phone and going to the party
So if she did bad the second cowboy Sighting was inevitable as she would always reference that party as to where it all went wrong for her and she ended up 'doing bad'
Final question - well why choose a cowboy?
Well as I said I think he represents last chance
Last chance Saloon
who drinks in Saloon bars...??

That's a really interesting point of view and I never read about such a theory before.
The "meet me once or twice" thing would make much more sense this way.
I also never thought about the possibility that Camilla could still be alive during Diane's dream.
Next time I watch the movie I will keep this theory in mind and think about it.
Thanks for sharing!