Underground rap suffered a bad patch for awhile there in the mid-'00s. It was hard to have fun listening to music that didn’t even sound like it was remotely fun to make, and so much of it felt like attending a lecture that you immediately knew you didn’t want to be at. Besides, it’s an insular world, built on obsessive minutiae and indecipherable jokes, and is usually defined by a focus on lyrics over song structure. If you have ever cared about underground rap, you have not only thrown the word "lyricism" around with abandon, you’ve also debated what it really means for 27 years of your life, even if you are only 16. It’s a commitment so heavy that it transcends space and time.
In recent years, though, that’s changed. Thank Earl Sweatshirt. Or thank Kendrick Lamar. Or the new generation of ears trained on MF DOOM's every move. Let’s thank Madlib, too, while we’re at it. The perma-stoned Oxnard producer has been tirelessly working with obscure samples for years, pushing them away from their source material so they take on strange new lives. He’s been a guiding light for a whole new wave of rappers and producers, directly and indirectly helping them shake off the arbitrary rules of a genre that thrives on breaking them.
Enter Chester Watson, a Florida teenager who sits so comfortably and skillfully amongst his influences that he already feels like their peer. His latest release, Past Cloaks, from a new label called POW Records—a project of Pitchfork contributor Jeff Weiss—is an actual cassette, which means that the more you play it, the more it’ll degrade, before eventually breaking down entirely.
But you’ll probably stream this somewhere—I’m streaming it right now—and the beauty is that you don’t lose much of the crust and murk when you listen to it digitally. That’s largely thanks to the production: a hodgepodge of repurposed beats, some done by Watson himself, and some done by a crew of in-house producers like Psymun, Art Vandelay, DRWN, and a bunch more. They’re all working within similar parameters: cracked psychedelia, off-kilter weirdness, and a dedication to a lifestyle with time built in for Saturday morning cartoons, cereal, and pontificating about the world through blunt smoke.
Past Cloaks is, in a way, a very necessary compilation tape. True to underground rap fashion, Watson’s discography is already daunting, but by pulling together material he’s recorded over the past few years—unreleased or otherwise—he’s dialed in on the mythology that he’s been building, focusing it in an unexpectedly breezy 19-track sequence that pulls warbly samples from damaged-beyond-repair records and snatches of TV dialogue, flipping them into compositions that fit together like melted puzzle pieces.
Watson is a formidable rapper, and wastes no time making sure we know that. On opening track "Phantom," his blunted voice bounces like a half-deflated basketball over keys that sound like they’re being played through an inch of dust. He’s a stream of consciousness rapper, letting vivid moments emerge and then quickly disappear. The entire tape feels like a casual studio session, with guests occasionally flitting in and out, and Watson holding court next to a stack of paperbacks, rapping about the virtues of getting stoned and seeing the world in sepia. It’s the kind of unbridled creativity that feels somehow untampered with.
Watson’s still in the early stages of what will hopefully be a long career. Which means that sometimes, like on "Purple Leaves," he sounds so much like Earl Sweatshirt that it’s a little distracting. But he’ll continue to develop, and there’s so much promise and endlessly re-playable material here that even the overly referential stuff is a pleasure to listen to. Besides, Watson could do a lot worse than look to Earl for inspiration—especially when he casually drops lyrical gems like "sippin' syrup in my room and all my clothes are out." This is the kind of mundane-yet-telling detail that feels bound to cultivate a loyal fanbase.
Speaking of loyal fanbases: There’s another thing you can do with tapes besides listen to them degrade. You can pass them around. Pocket them. Lend them to people. Make dubs of dubs until the original takes on a near-mystical quality. Past Cloaks isn’t perfect enough to be canonized, but it’s strong enough to form a small cult around.
