He used to play in club Tit for Tat.
He is a huge fan of Motown, Philly Sound and Country & Western, in addition to Jamaican legendary labels Studio One and Treasure Isle, and Reggae production in particular.
Sly was a drummer for the Skin Flesh and Bones band before forming Sly and Robbie.
Nicknamed Sly after Sly Stone, one of his favorite musicians.
He together with Robbie also played on Bob Dylan's albums Infidels and Empire Burlesque (using recordings from Infidels sessions).
As a member of Word, Sound & Power, he backed Peter Tosh on the album Mystic Man.
He has played for The Aggrovators for Bunny Lee; The Upsetters for Lee Perry, The Revolutionaries for Joseph Hoo Kim... Recorded for Barry O'Hare in the 1990s.
Together with Robbie Shakespeare, he formed Taxi label in 1980. It has seen releases from many international successful artists, including Black Uhuru, Chaka Demus & Pliers, Ini Kamoze, Beenie Man and Red Dragon.
He is humorously sometimes referred to as Sly Drumbar, while 'Robert 'Robbie' Shakespeare' as Robbie Bassspeare.
With Robbie Shakespeare, he is one-half of Sly and Robbie, reggae music's most prolific and long lasting production team. They are considered originators of the "Rockers" rhythm. They started working together in the mid 1970s, after having established themselves separately on the Jamaican music scene.
With Robbie Shakespeare as Sly and Robbie, he is one of the personalities mentioned in the song Genius of Love by Tom Tom Club. The others mentioned were Bob Marley, Smokey Robinson, 'Hamilton Bohannon', George Clinton, Bootsy Collins, and Kurtis Blow.