He was a Jamaican bass guitarist and record producer, best known as half of the reggae rhythm section and production duo Sly and Robbie, with drummer Sly Dunbar. Regarded as one of the most influential reggae bassists, Shakespeare was also known for his creative use of electronics and production effects units. He was sometimes nicknamed "Basspeare".

As a part of Sly and Robbie, Shakespeare worked with various reggae artists such as U-Roy, Peter Tosh, Bunny Wailer, Dennis Brown, Gregory Isaacs, Sugar Minott, Augustus Pablo, Yellowman, and Black Uhuru. His production work also extended beyond the reggae genre, covering various pop and rock artists such as Mick Jagger, Bob Dylan, Jackson Browne, Cyndi Lauper, Joe Cocker, Yoko Ono, Serge Gainsbourg, and Grace Jones. Prior to his involvement in Sly and Robbie, he was a member of the session groups the Revolutionaries and the Aggrovators.[