The youngest son of Patrick Sillar, a tenant farmer of Tarbolton, David Sillar was raised in conditions notably similar and proximate to those in which his contemporary and friend Robert Burns flourished. The French Revolution briefly prompted Sillar to some political engagement in the early 1790s, but his initial enthusiasm soon foundered, and he resumed his career as a master in a small village school. His Poems were published at Kilmarnock in 1789 by John Wilson, a recurrent champion of the labouring-class poets of Scotland; Sillar presumably came to Wilson's notice through Burns, a mutual friend. In 1840, James Paterson counted Sillar as a lesser talent among the many Scottish contemporaries of Burns: 'His Pegasus is none of the thoroughbred Medusian blood, and is sometimes so "be-devill'd wi' the spevie" that it is with difficulty she can be kept on the road'.