Minstrel Boy by Chris Gregory explores Bob Dylan’s changing artistry between 1967 and 1990.
Literary commentator Chris Gregory returns in October 2025 with Minstrel Boy, the second entry in his insightful trilogy Picasso of Song. This volume builds on the foundation of his earlier work Determined to Stand, shifting the spotlight to Bob Dylan’s evolution during the years 1967 to 1990.
Through a careful blend of scholarly analysis and narrative storytelling, Minstrel Boy explores a dynamic phase in Dylan’s life—one marked by creative withdrawal, unexpected revival, and artistic rebirth. Gregory brings an expansive perspective to the subject, tracing cultural influences ranging from folk and gospel to the poetry of William Blake.
Recognized by Leonard Cohen as the ‘Picasso of Song’, Dylan’s multifaceted career is examined with a nuanced and empathetic approach. “This book offers the depth of academic study but is written to be accessible and enjoyable to fans and general readers alike,” Gregory notes. 
With in-depth looks at Dylan’s evolving musical palette and lyrical innovations, the book also features rich commentary on his genre-blending tendencies, including blues, country, and rock and roll. Live performances are described with energy and detail, offering a full picture of Dylan as both a songwriter and a stage presence.
Gregory’s talent lies in balancing rigorous critique with a genuine love for the material. His writing captures both Dylan’s intellectual depth and his cultural resonance, bringing clarity to one of music’s most elusive figures.Minstrel Boy affirms Gregory’s role as a leading voice in Dylan scholarship, offering both new insights and a passionate engagement with the music that continues to inspire generations.
