He’s one of our country’s best writers, and he knows a whole lot about music (it shows up all over in Fortress of Solitude, for example).  Rolling Stone has him talkin’ about singin’:

This points to what defines great singing in the rock-and-soul era: that some underlying tension exists in the space between singer and song. A bridge is being built across a void, and it’s a bridge we’re never sure the singer’s going to manage to cross. The gulf may reside between vocal texture and the actual meaning of the words, or between the singer and band, musical genre, style of production or the audience’s expectations. In any case, there’s something beautifully uncomfortable at the root of the vocal style that defines the pop era.