A new major study of Bob Dylan’s mid-career years is set for release in October 2025. Minstrel Boy: The Metamorphoses of Bob Dylan, written by literary and cultural commentator Chris Gregory, offers an in-depth look at Dylan’s development as an artist between 1967 and 1990. As the second installment of Gregory’s Picasso of Song trilogy, this book builds upon the foundation laid in his previous critically acclaimed work, Determined to Stand: The Reinvention of Bob Dylan. We caught up with the author to talk about the book.
Your trilogy is structured in reverse chronological order. What did that unlock for you in
writing about Dylan’s 1967–1990 metamorphoses that a straight timeline wouldn’t?
“Beginning with the later period in ‘Determined to Stand’ helped me conceptualise the
elements of Dylan’s later style – especially in terms of ‘cultural borrowing’. But whereas
the Post-1990 work could be said to have a unifying aesthetic, the ‘middle years’
covered by ‘Minstrel Boy’ were characterised by a process of constant change and
evolution. Structuring the trilogy like this helped me to detach myself from the usual
chronological story that surrounds Dylan in order to focus more closely on the
development of his song writing and performing techniques. I also though producing a trilogy in reverse was a suitably ‘perverse’ approach to the work of an artist who rarely does anything in a conventional way!
Collaboration shadows this period—The Band, Jacques Levy, Mark Knopfler, Daniel
Lanois, Sly & Robbie. Which collaboration most changed Dylan’s writing or
performance habits, and what evidence convinced you?
Playing with The Band on The Basement Tapes was a collision between folk music,
literature and country and blues styles, out of which came the amalgam that came to
be called ‘Americana’- a musical revolution. The work with Levy was also highly
original in that they created a series of ‘cinematic’ songs together. Some of the
collaborations in the 80s were less successful, although Lanois’ work on Oh Mercy
was highly innovative.
You describe writing with “ironic humour” and accessibility while retaining academicdepth. What’s a passage or analytical move in Minstrel Boy where you felt that
balance click into place?
Perhaps the opening description in Chapter One about buying the original bootlegs or
my ‘sterling defence’ of ‘Wiggle Wiggle’!!
Your site and podcast are dialogue-driven spaces. Did reader/listener feedback ever
send you back to the archives or a bootleg to rethink a long-held view?
Very rarely. I get the occasional in depth comment though.
If “Picasso of Song” is the guiding metaphor, what’s Dylan’s cubist moment between
1967 and 1990—where form itself gets fractured and reassembled—and how do you
hear that on record or on stage?
‘Blood on the Tracks’ is the key moment, when he began to introduce multiple
perspectives, time shifts etc into the songs – especially in ‘Tangled Up in Blue’ and
‘Idiot wind’. Also these songs move through many different versions. The influence of
Picasso in particular means that meaning in the later songs is never fixed.
The “born-again” years still polarize fans. How did you approach those albums and
shows to balance cultural context, spiritual intent, and musical craft without collapsing
into either apology or dismissal?
A difficult task! Especially as so many of the earlier Christian songs tend to try to
eliminate the ambiguity which is such a strong feature of Dylan’s work. I have praised
the many live performances of the ‘religious era’. Some of the songs could be
discussed fairly briefly as their lyrics are minimal. One must assume that Dylan was
sincere in all his protestations of this period. What I found especially interesting was
the link between the ‘gospel’ and ‘post gospel’ songs, in which we can trace Dylan’s
embrace of a much broader religious viewpoint. In late ‘80s songs like When the Night
Comes Falling From the Sky and Ring Them Bells we also see him casting scorn of
religious cultists. In general I have tried to treat the religious material respectfully,
without trying to ‘psychoanalyse’ Dylan’s reasons for embracing religion.