Leonard Cohen and Tori Amos. There is one song out where he reads and then she sings, but not together. I think their voices would make a wonderful juxtaposition.
Mark Eitzel (of American Music Club) and Mark Kozelek (of Red House Painters)
I also think it'd be mildly interesting to hear Ian Curtis (if not deceased) with the singer of Interpol, who I'm guessing would sulk off the stage or out of the studio in shame.
I also think it'd be cool to hear The Cure and New Order or The Cure and Depeche Mode do something together. I don't really like Depeche Mode, but since they're like-minded fans of each other...
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