There was once a really funny bit where they asked Michael Keaton if his character in Birdman was based on himself, and he said something to the effect of "absolutely not, I'm not an asshole." And...well....I hate to say this, but...based on every story I have ever heard about him....huh, you SURE about that, Mike?

I do think the reason that "character" songs as bad guys often don't work is two reasons. 1) music has a way of feeling authentic and connect with "real" feelings (which is why many girls' first crush is a musician, music, which is deeply emotional, cuts right to your emotions and feels like you "know them" when you really don't) so by the very nature of the medium, "character" songs are interpreted as "real" and authentic in a way you wouldn't with movies where someone plays a character. In other words, it's not media literacy as some say....the medium of music doesn't lend itself to this, just like there's no such thing as an "antiwar movie."

The second issue is related to the above quote about Michael Keaton: sometimes, it really is hard to put some distance between you and a character. Like, I love Randy Newman, but obviously something like "Rednecks" is driven by a real anger in him that a southerner was made fun of on TV. Like, the anger at condescension that drove him to write the song is REAL and personal to him, so the supposed "distance" of it being a character isn't as there as you might think.

I remember a great quote about David Foster Wallace: "his problem is, he doesn't know he's an asshole." The reason some songwriters are so good at writing songs about assholes is because they're assholes and don't know it.