Born in Hackney, East London to Jamaican parents, Cleveland Watkiss is one of nine children, his father being a carpenter, DJ and frequent attendee to Ronnie Scotts. At the age of 16 Cleveland startetd studying engineering, music and drama and became a central cog in the wheel of Lover's Rock during the late 70`s. Soon enough, he was working with the likes of Carroll Thomson and Jamaican legendary vocalist, Sugar Minott.

Cleveland then took a lead role in the European production of the musical "Hair", soon after extending his studies to voice, guitar, piano and composition. In 1995, alongside Courtney Pine, Cleveland was one of the co-founders of the vastly influential Jazz Warriors big band. Cleveland was then entered for the Wire / Guardian Jazz Awards and was voted best vocalist for three consecutive years.

During his time performing with the London Community Gospel Choir he recorded the track "Free" for Stevie Wonder's album, "Characters?. Soon after, Cleveland featured on Pete Townshend's concept album, "The Iron Man" and joined Townshend and the rest of the Who in 1989 for their 25th Anniversary tour of the U.S.A.

Some time after the release of two critically acclaimed albums for Polydor Records, "Green Chimneys" and "Blessing in Disguise", Cleveland formed the drum'n'bass trio "Project 23" with American drummer extraordinaire Marque Gilmore and UK garage pioneer DJ Le Rouge. Their album, "23" was released on the Dorado record label to critical acclaim.

Cleveland then was invited by Goldie of MetalHeadz to record vocals on the ballad "Adrift" from the ground-breaking album "Timeless". Afterwards Cleveland spent two years as the original resident vocalist/MC at the world famous Blue Note Club. Around this time, he began his long time collaboration with his friend Talvin Singh multi-percussionist extraordinaire, and Mercury Prize winner.

In 2002 Cleveland Watkiss released ?Victory?s Happy Songbook?, his first solo album in a decade as well as his first release with INFRACom! presenting eleven songs full of soul, jazz and spirituality. Together with Kabuki, mastermind of Megashira, Cleveland Watkiss also produced the drum'n'bass track ?After the Fire?.