The son of a Flemishcalligrapher and fencing master, David Bailly first apprenticed to a local painter in Leiden and then to a portrait painter in Amsterdam. He worked for a short time as a journeyman in Hamburg before traveling to Venice and Rome at the age of twenty-five. On his return voyage, Bailly probably worked for several German princes. Back in the Netherlands in 1613, he established himself as a painter of vanitas still lifes and portraits. He executed many small-scale drawings of fellow artists and students and professors at the University of Leiden.
In his painted portraits, Bailly depicted attractive and expressive subjects in lively domestic settings. His vanitas paintings included the usual symbols of the transience and impermanence of human life, such as skulls, flowers, and burning or extinguished candles. He also included portraits of himself in these paintings, meaning to illustrate the ephemeral nature of his own artistic accomplishments. Though he sometimes intended his drawings as models for engravings, more often he made them as independently displayed works of art.