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The man who would later be known as Sole, one of the founders of the avant-garde indie rap label/collective Anticon, was born in 1977 in Portland, Maine, as Tim Holland. By 1992 he had made his first demo, attracting interest from EMI, whose deal Sole declined when he was told he could have Jermaine Dupri as his producer, and not DJ Premier. In 1996, with his group Live Poets, Sole released What's It All About, which brought him into contact with like-minded rappers (and future Anticon members) Doseone and Jel. In 1998 Sole formed Anticon with longtime friend Pedestrian in response to what they saw as a closed-minded and stagnant mainstream rap scene, and Sole and Pedestrian moved out to the Bay Area to officially start their label.
Soon after, Deep Puddle Dynamics (made up of Dose, Jel, Slug, Sole, and Alias) recorded their first album, The Taste of Rain...Why Kneel, and introduced Anticon to the world. In 2000 Sole released his debut, Bottle of Humans, and followed it up in 2003 with Selling Live Water. In 2004, frustrated with life in America, he relocated to Barcelona, Spain with his wife, and Live from Rome, his third studio album, came out the next year. Under the pseudonym Mansbestfriend, Sole has also recorded and self-released three albums (the Mansbestfriend, Pt. 1  and Pt. 2: No Thanks  CD-Rs and 2005's My Own Worst Enemy), one with the German label Morr Music, 2004's The New Human Is Illegal, and one, 2007's Poly.Sci.187, with his very own Anticon.
Along with that release, 2007 brought two more Sole offerings: the Exhile EP and the collaborative full-length Sole and the Skyrider Band. A remix album featuring Odd Nosdam and Dosh, among others, arrived in 2009. Two years later he would leave Anticon and release Hello Cruel World on the Fake Four label. The album featured his Skyrider Band once again, along with more accessible pop productions. In sharp contrast, his 2012 effort A Ruthless Criticism of Everything Existing was aptly titled and inspired by his involvement in Denver's Occupy political movement.