He is also co-founder of Carib Gems and Pressure Sounds, and founder of Hitrun Records as well as Green Tea Records and Soundboy Records. His most well-known label is On-U Sound.
During the early 80’s he brought together many Jamaican artists under the collective name of Singers & Players including Prince Far I, Mikey Dread, Bim Sherman and many others, this helped promote the individual artists at the same time as promoting the On-U Sound label. In 1986 he began working Jamaican dub producer and singer Lee Perry. They produced the classic album ‘Time Boom X De Devil Dead’ and Sherwood’s support helped relaunch Perry’s career.
He made contributions to the Industrial music genre in his remix of Einstürzende Neubauten’s song ‘Yü Gung’, on the album ‘Halber Mensch’, as well as his production work with Ministry, Cabaret Voltaire, KMFDM, Terminal Power Company and Nine Inch Nails.
Sherwood has also contributed to the blues, with his Little Axe project with Skip McDonald, producing his album on Real World Records, ‘Champagne and Grits’ in 2006.
In 2006 he released his second album ‘Becoming A Cliché’ that again featured numerous artists such as Lee “Scratch” Perry, the late Bim Sherman, Dennis Bovell, Little Roy, Leigh ‘LSK’ Kenny, Samia Farah, Raiz and Mark Stewart. A limited 2-disc version was released simultaneously with the second disc titled ‘Dub Cliché’.