Curious, why do you call hip hop a guilty pleasure?
Because I'm a middle-aged, suburban white guy and I'm sure I look plenty silly busting out the Biggie, for example.
The music speaks of a life I know nothing about and often uses extremely inappropriate and offense language that I don't condone or use generally myself. So I feel a bit guilty when I'm jamming it and singing it at the top of my lungs. And I'm sure it ain't pretty.
I'm aware that some seminal artists like the Beastie Boys (whom I love) defy the stereotype, but they are the exception.
And I should clarify that what I'm talking about would be considered "old school" rap/hip-hop. I started with Blowfly on vinyl back in the day, then Sugar Hill gang. Growing up in Stratford near the Bridgeport line, I was among the minority on my Pop Warner and Little League teams as a Caucasian, and our teams would routinely sing every word on the bus, with some memorable choreography, so the seed was planted early for me to like a lot of what would follow, up through about Public Enemy, N.W.A., Run DMC, Biggie, Snoop, Beastie Boys, Dre, Wu Tang and Jurassic 5, which is probably about as recent as I get with the genre. I don't know or listen to any of the more recent hip hop or rap artists. The Backspin channel on Sirius captures most of what I'm talking about (it's a preset for me).
But the question of genre always blurs for me. Some say that Dylan's "Subterranean Homesick Blues" was one of the first rap songs; others trace it back to Gil Scott Heron--and I love them both.
Americana really does seem to capture the "roots" that cross a lot of the music I love, which can probably all be traced to the Blues. As Wynton Marsalis put it when I saw him speak at Yale, the Blues is to good music as olive oil is to good food.
And to come full circle with that, I present perhaps the best cover ever, by a great band from Austin, the Gourds. I've seen them a couple times at Rhythm & Roots, including on the day that Dr. Dre's son died, when they played this song and were remarkably respectful and irreverent at the same time, as they segued into "Amazing Grace" at the end when it mentions him, and then back into the song again:
