I refute Lester Bangs's "cool" speech
Or at least part of it. It's true that a great many songs, most of the very good ones, are written about heartache and rejection, but most of those songs were written by guys who continually got laid and were essentially cool guys harping about not being cool. Then said music was/is packaged and marketed to the actual uncool guys who take it as their own creed.
Bo Diddley, Chet Baker, Elvis, Dylan, Syd Barrett, the Beatles, Hendrix, Zepplin, Iggy Pop, the Ramones, Kurt Cobain...it would be harder to name a rock star who truly did embody the "loserdom" that he shilled, as opposed to these other guys.
Only Morrisey comes to mind, off hand. And I guess Janis Joplin was pretty unlucky in love, from what I've read.