With Otis Taylor, it's best to expect the unexpected. While his music, an amalgamation of roots styles in their rawest form, discusses heavyweight issues like murder, homelessness, tyranny, and injustice, his personal style is lighthearted. "I'm good at dark, but I'm not a particularly unhappy person," he says. "I'd just like to make enough money to buy a Porsche."

Part of Taylor's appeal is his contrasting character traits. But it is precisely this element of surprise that makes him one of ...