Kail "True Hollywood Squares" (Alpha Pup)
There may be oodles of verisimilitude on True Hollywood Squares, but don't go looking for any obvious insight into Kail himself. The Tinseltown rapper skillfully skewers the half-baked egos in his run-down corner of the 'hood, and he's capable of showing sly sympathy at times, too. But the disc -- a Prince Paul-ish concept album based around nine fictitious Squares characters -- essentially amounts to 50 minutes of context: Flashes of Kail might be found in the cocky "John Booboo," the boorish "Sweet Dick Willy" and the blunt "Realest Muthafuckin' Tour Guide Ever," but those dudes are merely sharp caricatures. (The two "contestants" -- a foulmouthed guido and a cranky Brit DJ -- are just plain stoopid, and the show's host is perfectly archetypal.)
The real truth is that Kail has the confidence of a comic and the verbal aptitude of a language-arts aficionado, so almost every song is packed with vivid, off-kilter couplets like this one about "Peter Pennyworth," a failed casting agent who panhandles now: "The story of my life went from Windsor on ice/To hittin' up dumpsters for rice," Kail raps, assuming the tone of a guy who has retained only a few tatters of his old charm. The women, by contrast, are often addressed in the second or third person: The hooker "Wendy" inspires a mix of bemusement and self-protection; the scrappy love-target "Cola" gets a few rounds of contentious dialogue and some almost-sarcastic crooning. If anything, those songs are incisive-but-oblique admissions of immaturity; of course those girls are either shady or crazy, but what is he really afraid of?
The MC sure can emphatically pick out a beat, though: "Hawaiian Silky" is a remarkable amalgamation of tick-tock rhythms and decadent flapper jazz; "John Booboo" offers a prime example of how contemporary pop-rap aesthetics can be done on the cheap; and the blippy backing track of "Wendy" is some virtuoso 8-bit shit. But it's the "Commercial Break" that perhaps gets closest to Kail's most intimate self: "If you're like the millions of women who suffer from social discomforts every weekend, you know that sexual anxiety can easily take the life out of your night. ... Taken nightly in wine or mixed cocktails, Roofie XL begins working in just minutes," says a female voice over a Kanye-fied soul-sample loop. No, Kail isn't a pervert or a criminal; he's an older Wayans brother trapped in a younger rapper's body.
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