For me it's not necessarily about the musicality, it's more about the delivery.
Some people who have experienced life's highs and lows seem to express that in their voices. Both Townes Van Zandt and Chet Baker have voices which wouldn't be considered as musically great, but they can make both make a sad song sound even sadder and put a blue edge on a happy song. They could sing the phone book and make me cry.
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sj