"I always wanted to be the voice of the streets/But my father was a rabbi and my mother made beats... I mean, books/And the kids from the streets gave me dirty looks," whispers why? on "Cold Lunch," a typically eccentric ditty on his debut solo disc, oaklandazulasylum. These lines prove that hiphop just doesn't have enough messianic rabbis' sons in the game. Yeah, the genre's spawned some skilled Jews (e.g., Beastie Boys, 3rd Bass, Paul Barman), but Cincinnati-born Yoni Wolf is the first kid from rabbinical stock to put a stamp on the Bronx's finest export.

But seeing as oaklandazulasylum comes from anticon records, hiphop signifiers are only obliquely alluded to. This album's more about shmoes than hoes, and why? sounds more like Tuli Kupferberg (of lo-fi hippie pervs the Fugs) than Eminem or Everlast. Further quirking up things, why?'s bedroom production is sparse and his tracks' trajectories and instrumentation unpredictable: Acoustic guitar, dulcimer, cello, hurdy-gurdy, and analog synths swirl around spindly beats that won't be booming from any Jeeps this summer.

As part of cLOUDDEAD, whose self-titled 2001 album is an underground hiphop classic, why? provides the distinctive whine to that group's soupy psychedelic sound collages. His voice takes some getting used to, but once you do, you'll really hate it. But seriously, why?'s Midwestern nasality is the perfect vehicle for his odd thoughts, which come off like Woody Allen after reading the Beasties' Grand Royal fanzine. In short, oaklandazulasylum is hiphop with all the ghetto and head-nodding removed--and it's fantastic.

I wonder if why? thinks his outsider status is an advantage? "I'm an insider in my own world," he says. "I'm an outsider in many circles, including the carnival crowd, Islam, Catholicism, the Crips, the cops, and, yes, hiphop. [But] I don't think this really has any bearing on anything."

Does why?'s Jewish background affect his art? Have any Jewish rappers influenced him? "I think, when writing music, I sometimes revert to cantor melodies I heard when I was a child. [But] I don't think I have particularly been influenced by Jewish rappers."

Both why? and the anticon label moved to the Bay Area recently. Of the region's pleasant weather, why? says, "[It] helps keep me from deep depression. I can't work when I'm in a deep depression, so in that sense I guess it's more inspiring--or less prohibiting [than Cincinnati]. I think each city yields its own artistic conclusions. Maybe if I stay here too long, I will start sounding like the Beach Boys or some other happy-ass shit."

Why? also appears in the DVD Mush Tour Spring 2002 with his Reaching Quiet and cLOUDDEAD ensembles. The 85-minute DVD includes performances from Boom Bip & Doseone, Labtekwon, and Radioinactive, taped at shows held at L.A.'s El Rey and San Francisco's Great American Music Hall. With its casual, handheld camerawork heavy on quick cuts and goofy juxtapositions, Mush captures the mundane surreality common to nationwide tours.

What makes the DVD noteworthy is that Mush Records--along with anticon, its mysteriously affiliated sister label--has forged one of hiphop's few new approaches over the last five years. Artists from both camps have pushed intellectual, obliquely humorous agendas using nerdy, whiny deliveries more redolent of nutty poetry profs than of rap icons like Rakim and Notorious B.I.G. With the exception of Labtekwon's standard flows, nut-grabbin', and sports-paraphernalia-wearing, the musicians here flout or just ignore the genre's live conventions. In fact, Reaching Quiet aren't hiphop at all, but rather a lo-fi prog-rock band with rudimentary technique and wack melodies. They come off as the brainchild of Drag City "comedian" Neil Hamburger. By contrast, cLOUDDEAD (why?, Doseone, and Odd Nosdam) invest hiphop with unprecedented psychedelic atmospheres and textures (Dose and why? ruffle through money for percussion on one track) while mutating language into acid-laced dream logic, replacing rap's usual bravado with uncertainty, confusion, and angst. They wear cool masks, too, and Dose (arguably the star of the whole crew) rocks a porkpie hat, dollar-sign silver chain, and white fur coat.

Boom Bip & Doseone blaze similarly out-there trails on Mush Tour Spring 2002, molding psych-rock and avant-jazz's daring instrumentation to their advanced hiphop structures. Director Simon Chan aptly flashes plenty of LSD-influenced visual trails and double exposures during the duo's set, but, overall, his frequent blurs and montage effects of Mush's geeky, mostly white roster (and fans) in action don't make for the most entertaining eye confectionary.

However, Radioinactive's group nearly steal the DVD with their bizarre papier-mché foliage shawls and headdresses while executing Middle Eastern- and jazz-inflected hiphop featuring Radio's speed-freak raps. It may be weirdness for its own sake, but it's fascinating, hilarious weirdness. And those adjectives apply to the DVD and Mush's output in general. This next level's befuddlingly askew. DAVE SEGAL

Why? (featuring a full band), Dosh, Iguales, Wed Sept 3 at Chop Suey, 1325 E Madison St, 324-8000, all ages, 8 pm-2 am, $8 adv. Mush Records info at www.dirtyloop.com.

segal@thestranger.com