Works
It is likely that his earliest surviving poems are The Navigation and the related Cartel of the Thre Ventrous Knichts, which may well have been written for performance at court at Epiphany 1580. He came to prominence as "laureled" leader of the Catalian Band, a circle of court poets headed by the King after being declared victor over a rival poet, Patrick Hume of Polwarth, in a comically scurrilous flyting, or poetic duel. The King, who was himself a practising member of the group, referred to Montgomerie as its ‘maister poete’.
A number of Montgomerie’s poems can be assigned to the first half of the 1580s, including sonnets, court songs, and the first, unfinished version of his longest work, the allegorical Cherrie and the Slae. Like some other pieces, it may have been written (at least in part) by autumn 1584, for the 19 year-old king included a passage from it in his literary manifesto Some Reulis and Cautelis to be observit and eschewit in Scottis poesie, published around September of that year.
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