When I was in my mid-twenties, I taught adult ESL in Taegu, South Korea for a while. Although I no longer remember the lesson objective, one day I played my students the song "Bad, Bad Leroy Brown" on my guitar. After I finished, one of the students asked me, "Why would you play a song about a person who is bad?" That, I thought, was an interesting question. Why would a person go to the effort to write, learn, or perform a song about a person who is bad? Why would someone use their energy to essentially celebrate negativity? That was an interesting perspective and good food for thought.
In the Western tradition, songs about outlaws and other "bad guys" are legion, though here in Texas I have never heard anyone question why a person would write or play such a song. No, I have never heard a discouraging word against "The Ballad of Jesse James," "The Ballad of Sam Bass," "The Ballad of Billy the Kid," or any other such song. And while I agree that it's probably more constructive to sing songs about good people, it's still kind of fun to croon the ones about desperadoes as well.
For your listening pleasure, here is a song about a real rapscallion that I have always enjoyed.
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