Drummond's first publication appeared in 1613, an elegy on the death of Henry, Prince of Wales, called "Teares on the Death of Meliades" ("Moeliades", 3rd edit. 1614). The poem shows the influence of Spenser's and Sidney's pastoralism. In the same year he published an anthology of the elegies of Chapman, Wither and others, entitled "Mausoleum", or "The Choisest Flowres of the Epitaphs". In 1616, the year of Shakespeare's death, appeared "Poems: Amorous, Funerall, Divine, Pastorall: in Sonnets, Songs, Sextains, Madrigals", being substantially the story of his love for Mary Cunningham of Barns, who was about to become his wife when she died in 1615.