In the 70s, when he was all druggy and weird, David Bowie made one of the strangest—and coolest—duets of all time: a cover of “Little Drummer Boy” (?) with Bing Crosby (!). In the 80s, when he was all safe and pop, he recorded one of the most atrocious duets of all time: a cover of “Dancing in the Streets” with Mick Jagger. Three guesses which version of Bowie gets the most entries on this list.

David Bowie AllMusic page