I do love this thread, but I have to admit that actually turning this story/film into a musical sounds almost untenable: the problem would be that an essential aspect of so many of the characters is their inability to articulate, understand, or accept their feelings. These characters are people largely without access to expressive language, and as a consequence without access to many of the ideas that expressive language can convey. And a musical about inarticulate people is a contradiction in terms. Jack is more of a dreamer, and I could maybe see creating songs for his character -- but Ennis?! His entire tragedy derives the fact that he bottles up his feelings and refuses, or is unable, to put them into words; Heath Ledger's delivery of his dialogue captures this repression/oppression perfectly. To have Ennis able to sing about his feelings would undermine the most essential aspects of his character and the story itself.
On the lighter side, I'm thinking Elaine Stritch should have first dibs on the Randy Quaid character!
"Sweet summer evenings, hot wine and bread /
Sharing your supper, sharing your bed /
Simple joys have a simple voice:
It says why not go ahead?"