Recently I have been getting into the habit of diving deep into favorite songs — not just the song, but a particular performance. I listen to the performance repeatedly, trying first to recognize each decision the singer made, and then to figure out the reason for that decision.
A masterful singer will make hundreds of little choices over the course of performing a three minute song, from phrasing to pitch bend to rhythmic variation to vocal quality to pronunciation. Each of those choices has an effect on the overall emotional impact of the performance. The more I look at such performances, the more detail I find.
After listening to a performance I particularly like — say, Janice Ian performing “At Seventeen”, or Leonard Cohen singing “The Stranger Song”, or Tom Waits singing “Time” — I try singing the song myself while making exactly the same vocal choices. I don’t pretend that what comes out of my mouth would be pleasing to anyone else. The important thing is to notice what choices the singer made, and to become completely familiar with them, so I can start to figure out the purpose of each of those little decisions.
It’s an odd little hobby, but it’s great fun.