Minstrel Boy is Chris Gregory’s latest study of Bob Dylan, covering the years 1967 to 1990.
Arriving in October 2025, Minstrel Boy marks the latest release from literary and music analyst Chris Gregory. As the second volume in his Picasso of Song trilogy, the book investigates Bob Dylan’s artistic evolution across the 1967–1990 period.
Known for his thoughtful and multifaceted approach, Gregory brings together academic depth and cultural understanding to examine Dylan’s work during a time of significant transition. These years saw the iconic musician engage in creative retreats, return with bold new directions, and redefine his presence both on stage and in the studio.
Leonard Cohen once described Dylan as the ‘Picasso of Song’, a title that fittingly serves as the name of this series. Through extensive lyrical and musical analysis, Gregory reveals how Dylan’s creative process drew from an array of traditions including gospel, country, blues, and rock and roll. 
“This book offers the depth of academic study but is written to be accessible and enjoyable to fans and general readers alike,” Gregory says.
In addition to dissecting Dylan’s songwriting, Minstrel Boy brings to life his live performances, adding vivid texture and performance context. With references to literary figures like William Blake and commentary on genre fusion, Gregory adds dimension to Dylan’s story while maintaining clarity for general readers.
Building on the success of Determined to Stand, this volume offers readers a deeper understanding of Dylan’s restless creativity. Minstrel Boy is more than a biography—it’s a comprehensive exploration of an artist constantly in motion.
