The truth is, Matisyahu isn't really a novelty—his is the oldest act in the show-business book. Minstrelsy dates back to the very beginnings of American popular music, and Jews have been particularly zealous and successful practitioners of the art. From Irving Berlin's blackface ragtime numbers to Al Jolson's mammy songs—from jazz clarinetist Mezz Mezzrow, who passed as black, to Bob Dylan, who channeled the cadences of black bluesmen, to the Beastie Boys—successive generations of Jewish musicians have used the blackface mask to negotiate Jewish identity and have made some great art in the process.
Indeed, they have. And all art, to some extent, involves the fashioning and wearing of masks, so in this respect Matisyahu is, as Rosen suggests, comfortably within the American pop music continuum. This is aside from the fact that his tunes sound they were pilfered from vintage Casiotone demos and his lyrics strongly indicate that he has not in fact given up smoking dope. Like, a lot.
For me, when I want some brilliant, innovative Jewish music I go for Zorn. Electric Masada and Bar Kokhba are particularly excellent, and about as different from each other as Zorn's work is from the reast of modern jazz. His band's set at the 2002 Earshot Jazz Festival was also one of the most flat-out astounding musical performances I've ever experienced.
Reminds me of some funny: A few years ago Stu and I went to see the Seattle Chamber Players perform with Zorn at Seattle's Benaroya Hall. Almost as great as hearing the music itself was watching the stunned reactions of the staid season ticket holders as Zorn assaulted them with a ten-minute circular breathing free improvisation on alto saxophone. Good times, good times.