Billy Blue was an enterprising former convict of African-American origin (possibly born in Jamaica), who arrived in Sydney in 1801. He was appointed harbour watchman and constable by Governor Macquarie in 1811. He started a successful ferry service from Lavender Bay (later named Blues Point) to Dawes Point.

Unlike many portraits, this would not have been commissioned by Blue himself. East has depicted Blue as a celebrity or character, and presumably was hoping to capitalise on news of his death in 1834. Several print portraits of Blue were published after his death, all of which show him with a top hat and stick. The background to this portrait is Mrs Macquarie’s Chair.