Kail | True Hollywood Squares

Most Likely To: leave listeners scratching their heads.

On his debut full-length, True Hollywood Squares, Kail is about as antagonistic as entertainers come. He’s the sort of personality who places such a high premium on being different that he’d rather give birth to a record that is utterly disorienting than produce something that conforms in some measure to expectations. While his approach does lead to the occasional moment of inspired performance (as with the old-timey background loop on “Hawaiian Silky”), more often than not it means bursts of sophomoric humor, unlistenable skits, and ruining otherwise decent tracks.

This misplaced ambition is present from the outset: True Hollywood Squares is a concept album. As a matter of fact, it’s a concept album with two concepts. The first conceit is that of the “True Hollywood Squares” gameshow that is being “played” throughout the record, complete with a cast of poorly voiced stereotypes that pass as panelists. (Despite what the record label one-sheet suggests, it shouldn’t be a point of pride that Kail handled all of the thin accents himself.) The second conceit is that the tracks that fall between the skits serve as neighborhood tours of the greater Hollywood area.

Where the first is concerned, the show is simply–for lack of a more appropriate term–retarded; there is no desire to listen to the first thirty seconds of the show, let alone its reprisal every track. As regards the second, there is considerably more potential here, especially when Kail relates moments from his personal history and tethers them to specific streets and hoods. However, it always seems to fall apart when he slips into a juvenile coma. “The Realest Muthafuckin’ Tour Guide Ever” actually concludes with a the remarkably dated sounds of a cheap foley drive-by. That may have worked for N.W.A. once upon a time, but now you’d be hard pressed to think about something more hackneyed in a west coast rap song.

Being an antagonist, Kail can’t simply deliver a contrived disappointment of a record. He has to throw in a few tracks that are truly sensational, just to frustrate, just to confound, just to show that he (maybe?) could put out something consistent from start to finish. “Wendy” still has some cringe-worthy moments, but its eight-track beats are sensational and his flows about his “mad MySpace friend requests”–delivered in his best Kanye West impression–are riveting. When you trim the half of “Motorola Twins” that isn’t inane filler, you’re left with a killer track with lyrics like “The Sidekick got Yahoo Maps, so when I find a spot to follow through at / Then I promise I’ll call you back / My Moto’s on slow charge / In this structure I get no bars / So I just left it in Sho-Sho’s car.” It’s irreverent and tight, but ultimately it’s just a tease.

So what’s the deal? Kail is clearly talented, obviously has an ear for sounds that are different and intriguing, so why put out a product that doesn’t match those rare moments of brilliance? My guess is that he’s more interested in being confrontational and developing an aura around his personality than he is putting out an album that will sell a shitload of copies. There’s nothing wrong with that, either, but for his fans and followers of his Customer Service crew it all feels a little bit like a cheap date.