Minstrel Boy – Chris Gregory’s Definitive Study of Bob Dylan
Picasso of Song – Volume Two
Author: Chris Gregory
Book: Minstrel Boy The Metamorphoses of Bob Dylan
Release Date: October 2025
Following the success of Determined to Stand: The Reinvention of Bob Dylan, literary and cultural commentator Chris Gregory returns with Minstrel Boy, the second volume in his ambitious Picasso of Song trilogy — a deep-dive analysis of Bob Dylan’s creative journey. Scheduled for release in October 2025, Minstrel Boy examines Dylan’s artistic metamorphoses from 1967 to 1990: a period of retreat, resurgence, and rebirth.
Described by Leonard Cohen as the ‘Picasso of Song’, Bob Dylan remains a towering figure in music and literature. Gregory’s trilogy captures the complexity and brilliance of Dylan’s songwriting and live performances with both scholarly insight and fan devotion. Minstrel Boy brings together critical analysis, biographical context, and cultural references—ranging from William Blake to gospel music—to explore Dylan’s poetic and performative evolution. Chris writes with great sympathy and openness to different interpretations, with much use of ironic humour.
Chris explains that “This book offers the depth of academic study but is written to be accessible and enjoyable to fans and general readers alike.” He also brings to the text a deep knowledge of the various forms of popular music and comments in detail on the influence of folk, blues, country, gospel and rock and roll on Dylan’s work. The book’s textual analyses are broken up by lively descriptions of Dylan’s many and varied live performances.
Minstrel Boy is divided into three parts:
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Retreat (1967–1973): Dylan steps back from the limelight, embracing country sounds and introspection.
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Return (1974–1978): A creative resurgence that includes some of Dylan’s most acclaimed recordings and tours.
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Rebirth (1979–1990): From his spiritual conversion to another artistic pivot, Dylan continues to surprise.
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The trilogy, written in reverse chronological order, aims to become a definitive study of Dylan’s career. Volume Three, currently in progress, will explore Dylan’s early years.
Chris Gregory’s website From the Pen of Chris Gregory is a go-to resource for Dylan fans as it features blogs on hundreds of Dylan songs. It has received over 100,000 visits. Chris is also the host of the popular podcast Bob Dylan: A Headful of Ideas, with over 10,000 downloads and nearly 80 episodes, which has been praised for its deep analysis and human touch. This can be found on You Tube, Spotify, Apple Podcasts, Podbean, Buzzsprout and other platforms and has been identified on sites such as Feedspot, Player FM, and Million Podcasts as one of the top Dylan podcasts on the Internet.
Chris is also a novelist and a performing poet. He is the author of several other books on mass media topics including Be Seeing You: Decoding the Prisoner (1997), Star Trek: Parallel Narratives (2000), Who Could Ask For More: Reclaiming The Beatles (2009).
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Website: https://chrisgregory.org/