In 2016, he pulled off something not many expected 20 years after he first broke: a viral hit. Speaking in 2019, he calls his third true album a “provocation,” but it may represent the purest manifestation of his artistic approach: “The whole concept behind The Outsider was zig-zagging from extreme to extreme, but what I hoped people would think was, ‘Damn, there’s not a lot of people that could pull this off,’” he says.
Shadow responded to critics and a seeming insistence to box him in as a hip-hop purist with 2006’s The Outsider, a genre-hopping record that drew on the rap sounds dominating the Bay Area at the time while also incorporating folk and other unexpected genre forays.
That album, which today stands as one of his more satisfying works, received mixed reviews at the time. With Cut Chemist, he made two of crate-digging’s defining documents-the mixtapes Brainfreeze and Product Placement-before releasing Endtroducing’s true follow-up, 2002’s The Private Press. From there, things got interesting for Shadow.
