Just a couple of thoughts regarding what many will call the symbolic end of the twentieth century, the passing of Frank Sinatra:
For those who don't know his oeuvre, come to Sinatra through the trumpet. I did. I heard Sweets on "Songs For Swingin' Lovers" and was hooked. Other trumpeters associated with FS are Bobby Hackett, Conte Candoli, Conrad Gozzo, Al Porcino, Charlie Turner, Buddy Brisbois (listen to "Luck be a Lady" *sitting down*), Buddy Childers, and our own Walt Johnson and Rich Szabo. Get the bold and brassy swinging sets from the Capitol period and be amazed at the great writing for brass by experts like Billy May (himself a trumpeter) and Nelson Riddle.
His voice was *always* in the service of the music. He never fell in love with the sound of his own voice, like many singers, because that would have interfered with the musical and lyrical message. And he made the two parts of his craft (music and lyrics) equals in his interpretations: the notes *meant* the words. Listen to a song sung by, say, Ella Fitzgerald and then the same tune by Sinatra. Great as she was, she never came close to his projection of the *meaning* of a song.
Finally, Sinatra projected something even more subtle. It's taken me years of listening to get it, but it now permeates everything I hear. When you hear Sinatra, you hear the conviction that we, each of us, must find our own way. Alone. I get the exact same feeling from listening to Miles Davis play a ballad, and this is no coincidence. They both plumb the depths of the music to make sense out of it all, and the reason that they are both icons--sailing far beyond silly categories like "jazz" or "easy listening" (I shudder at the term), is that they are successful. Their music *means* something to the least initiated, least experienced, least critical listener.
To go beyond the superficial is the goal of music. To communicate beyond the power of language is the goal of music. To impart meaning beyond our own ability to articulate it and yet to *still understand* is the goal of music.
Frank Sinatra reached that goal.