Raeburn initially submitted a self-portrait (National Gallery of Scotland) as his diploma work but the Council, which did not permit self-portraits as Diploma Works, refused it. He presented Boy and Rabbit as a replacement in 1816.

The sitter is Henry Raeburn Inglis, son of Raeburn's stepdaughter, Ann Leslie. He is shown placing a protective arm around his pet rabbit as he feeds it dandelion leaves. The setting is informal and relaxed. The boy's proximity to the picture plane and Raeburn's broad handling of the landscape suggests a familiarity and ease which would have been more restrained in a commissioned portrait. It also allows Raeburn to demonstrate his virtuoso handling of paint, particularly evident in the treatment of the boy's shirt.

Henry Raeburn lived and worked in Edinburgh, selling his work to mainly Scottish patrons. He made efforts to break into the London art scene but always felt alienated from it. In 1819 Raeburn wrote to fellow Scotsman and Academician David Wilkie saying that the pictures he sent to the annual exhibition at the Royal Academy were

'merely.. an advertisement that I am still in the land of the living, but in other respects it does me no good, for I get no notice from anyone, nor have I the least conception how they look beside others.'