I think the litmus test is "is this person or song associated with any sort of subculture?" If the answer's yes, then Carlos Santana probably would not work with that person/cover that song, as he's only into things that are or were once popular. Of course, exceptions do spring to mind--e.g., Dave Grohl and most popular (or formerly popular) rappers--but only because they've had so much mainstream exposure and success that it serves to essentially scrub out their former associations with any sort of subculture. If you ask yourself that question and you're still not sure, ask yourself "Is this music that my cousins in Indiana would be aware of?"
That said:
Santana ft. Mark Everett - "Maggie May"
Santana ft. __________ - "Behind Blue Eyes"