​Cleveland was born in Hackney, East London to a Jamaican family. At age 16, he won twice in a local singing talent competition, hosted by “FatMan” of FatMan Sound System (North East London Based Roots, Reggae & Dub Sound System). Later he studied music at the London School of Singing and at the Guildhall School of Music and Drama thereafter. He was taught by the most respected coaches in the industry. He has worked closely and performed together with the diverse range of artists across the world, including Stevie Wonder, The Who, Richard Spaven Trio, Louis Moholo, Bobby McFerrin, Goldie, Björk, Talvin Singh, Bob Dylan, Keith Richards, Abdullah Ibrahim, Shabaka And The Ancestors, Nigel Kennedy, George Martin, Black Top, William Parker & Hamid Drake, Branford & Wynton Marsalis +JALC, London Community Gospel Choir, Royal Philharmonic Orchestra, London Chamber Orchestra and many others. He’s an original founder member of the Jazz Warriors, and now Co-Director of Warriors International. Most recently, for his services to music Cleveland has been appointed an MBE. He has also received multiple prestigious awards and nominations, including Jazz Vocalist of the Year at the Parliamentary Jazz Awards 2017 (Winner), Best Jazz Act at the MOBO Awards 2017 (Nominee), Best Vocalist at the London Jazz Awards 2010 (Winner), and Best Vocalist at the Guardian Jazz Awards (Winner) for three consecutive years.