DJ Shadow’s first full-length record, Endtroducing, was released in 1996 under James Lavelle’s Mo’ Wax label, and its dizzying, baroque assemblage of samples single-handedly extended the boundaries of experimental hip-hop by an order of magnitude. In the years since, Shadow has been restlessly tweaking and redefining his method and technique, only to double back and head off in a new direction with each project. His latest album, The Outsider, is an exercise in formal diversity, each track a surprising departure, melodic soul giving way to breathy, funk-laden ambience, which in turn yields the frenetic, loopy dissonance of an emergent style of rap known as Hyphy.

Jeff Chang is the author of Can’t Stop Won’t Stop, an innovative cultural history of hip-hop that traces the origin of the genre from its antecedents in Jamaica in the late 1960s, through its formal birth in the Bronx in the ’70s, to its transformative rise to mainstream dominance through the next quarter-century. Chang writes about hip-hop not as a style of music but as a force that runs parallel to the history that gave birth to it. He is currently editing an anthology titled Total Chaos: The Art and Aesthetics of Hip-Hop.

Long before Endtroducing was entered into the Guinness World Records for “First Completely Sampled Album,” Chang met Shadow working at KDVS, the college radio station at UC Davis. They formed the influential Solesides label with other nascent hip-hop groundbreakers such as Chief Xcel of Blackalicious and Lyrics Born, and released some of Shadow’s earliest singles in the early ’90s.

The two have kept in touch over the years. Shortly before the release of The Outsider, Chang met Shadow at his house in Mill Valley, where they had the following conversation.

I. BAMBAATAA’S CRATES

JEFF CHANG: I know every time you come out with a new record you’ve got to do the press, and every time there’s that one question that you don’t want to get, but for whatever reason it ends up being the one that everyone wants to know about.

DJ SHADOW: “Does hip-hop still suck in 2006?”

JC: Is that the one that people are asking?

DJS: That’s the one I’ve gotten every time I put a new record out. “Does hip-hop still suck in ’98?”“Does hip-hop still suck in 2002?”

JC: I guess you’ve got to live that down now.

DJS: I thought it was a clever title. I thought it was an evocative title—it didn’t really mean anything, particularly, but I just thought it sounded good. But I think people who don’t listen to rap but who got into my record saw it as, “Oh,...