[5] Watkiss was one of the co-founders of the vastly influential Jazz Warriors big band, and his vocals can be heard on their debut album, Out of Many People (1987), which won a video award in Japan.

Watkiss was then entered for the Wire/Guardian Jazz Awards and was voted best vocalist for three consecutive years, and was the opening act of choice for Cassandra Wilson and Abbey Lincoln.

Watkiss has performed with a diverse range of artists from around the world, including: Courtney Pine, Stevie Wonder, Shakatak, James Taylor Quartet, Working Week, The Who, Coldcut, Lisa Stansfield, Maxi Priest, Jason Rebello, Goldie, Björk, Talvin Singh, Om Unit, Bob Dylan, Jackie Mittoo, Keith Richards, Art Blakey, Sly & Robbie, Abdullah Ibrahim, DJ Patife, Carlinhos Brown, Wynton Marsalis and the Jazz at Lincoln Center Orchestra, Robbie Williams, Joe Cocker, Bobby McFerrin, Branford Marsalis, George Martin, Bocato Big Band, Janet Kay, Soul II Soul, Kassa Mady, Halogenix, Kenny Wheeler Big Band, Sugar Minott, London Community Gospel Choir, Malik & the O.G's and many more.

Reviewing a solo performance at The Vortex, Ivan Hewett wrote in The Telegraph: "Cleveland Watkiss is such a restlessly curious musician, it's hard to know where to place him.

He has sung with the Who and gospel choirs, he has appeared in straight-ahead jazz contexts and in drum and bass, he has worked with video artists, DJs, Indian percussionists, Japanese musicians.