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. The
Navigatioun involves the torchlit entrance at
Holyrood Palace of a narrator and his companions, a "Turk, the More, and the Egyptien". The court musicians were bought "mask claithis" comprising red and yellow taffeta with swords and daggers. Montgomerie's prologue alludes to the
Magi and
Epiphany to flatter James VI as the
Northern Star. James was also characterised as
Solomon. The masque was followed by dancing. Montgomerie came to prominence as "laureled" leader of the Castalian 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. ==Courtier==