What is the most challenging song to cover in the history pop music? Prince's "When Doves Cry" might get my vote.
Besides being totally iconic and associated with a singular voice and attitude like, say, "Billy Jean" or "(You Make Me Feel Like) A Natural Woman" or "Satisfaction" are, the song totally breaks down standard structural tropes and rearranges them in a way that seems to be a reflection of its author's most distinctive personal traits. Every little blip and tick and squealed note of "When Doves Cry" just sounds like the essence of Prince himself. Like he just sweat the song out in the midst the most personal dream he ever had. (Perhaps he ejaculated it, in that case?) [Ed. Note: DAVE! JESUS!]
So it's always seemed crazy to me that any other artist would attempt it. And extra impressive when folks have pretty well pulled it off. The Twilight Singers and Patti Smith have done commendable jobs. (It's Patti Smith week, here at the Awl!) Timbaland and Ginuwine hew a little too close to the original. And Ani Defranco, just, no. Kudos to Robyn for going for it—and sounding pretty good!