The songs I came up with off the top of my head were: "Fan Letter to Michael Jackson" by the Rheostatics "Frank Sinatra" and "Meanwhile, Rick James..." by Cake "Talkin' Woody, Bob, Bruce & Dan Blues" by Dan Bern and "Two Hearts" by Danny Michel.
"The mind of the thoroughly well informed [person] is a dreadful thing. It is like a bric-a-brac shop, all monsters and dust, and everything priced above its proper value."