[4] 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.

Later, the bass player Aston "Family Man" Barrett came into his yard, as it was near a popular location for selling marijuana.

[9] He collaborated with the drummer Sly Dunbar for the first time when they played in the Channel One Studio house band, which was called the Revolutionaries.

[13] With Joan Armatrading With Gary Barlow With Dennis Brown With Jackson Browne With Jimmy Cliff With Joe Cocker With Bootsy Collins With Carlene Davis With Ian Dury With Bob Dylan With Gwen Guthrie With Mick Jagger With Garland Jeffreys With Grace Jones With Ziggy Marley and the Melody Makers With Jenny Morris With Yoko Ono With Sinéad O'Connor With Augustus Pablo With Carly Simon With Simply Red With Barry Reynolds With Sting With Peter Tosh Shakespeare appeared in the 2011 documentary Reggae Got Soul: The Story of Toots and the Maytals which was featured on BBC and described as "The untold story of one of the most influential artists ever to come out of Jamaica" (see Toots and the Maytals).