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Chesnutt's music blends elements of rock, funk, soul, hip hop, and blues. After relocating to Los Angeles, Chesnutt found work with Death Row records, writing and producing five songs for the male R&B group Six Feet Deep. Chesnutt and his former band, The Crosswalk, had a brief stint with Hollywood Records in which they were later booted from the label. The band subsequently broke up and Chesnutt released a double LP in 2002 entitled The Headphone Masterpiece, which was recorded on a 4-track cassette recorder in his bedroom recording studio, which he calls "The Sonic Promiseland".