Sherwood was co-founder of Carib Gems and Pressure Sounds, and founder of Hitrun Records as well as Green Tea Records and Soundboy Records. He is also the fourth member of industrial hip-hop outfit Tackhead, credited as "mixologist".
During the early 1980s he brought together many Jamaican artists under the collective name of Singers and 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 Records label. He also worked with Suns of Arqa on many of their early records.
In 1986, he began working with Jamaican dub producer and singer Lee "Scratch" Perry. They produced the album Time Boom X De Devil Dead.
He made contributions to the industrial genre in his remix of Einstürzende Neubauten's song "Yü Gung" on the album Halber Mensch, as well as his production work with Ministry, Skinny Puppy, Cabaret Voltaire, KMFDM, Terminal Power Company and Nine Inch Nails. Sherwood has also delved into the blues, producing Little Axe's Real World Records release Champagne & Grits in 2006.
In 2003, Sherwood supported Blur at Wolverhampton Civic Hall. The same year, Sherwood released his first album as a solo artist, Never Trust a Hippy, which featured collaborations with various artists such as Sly & Robbie, Steven "Lenky" Marsden, Carlton "Bubblers" Ogilvie and Jazzwad.
In 2006 he released his second album Becoming a Cliché, again with numerous artists such as Perry, the late Bim Sherman, Dennis Bovell, Little Roy, LSK, Samia Farah, Raiz and Mark Stewart. A limited 2-disc version was released simultaneously with the second disc titled Dub Cliché.
On beginning a solo career, Sherwood stated: "I wanted to do some of my own writing and make something that was challenging for me... As a producer, it's my job to satisfy the artist foremost. I wanted to make something that was a little more aggressive and modern. I wanted to paint a picture that was contemporary, one that specifically showed where my brain was at. I've got to the point in my life where it's time for me to call all of the shots."
He produced the original score for the 2006 independent film Johnny Was, starring Vinnie Jones, Roger Daltrey and Samantha Mumba. Since 2015, Sherwood has been recording with Bristol dubstep artist Pinch; they have released two albums under the moniker "Sherwood and Pinch".