About this episode

The episode explores Bob Dylan's attempts to compete in the 1980s pop music scene against icons like Michael, Madonna, and Prince.

More ruminations on Dylan's strangest period when he attempted to compete with Michael, Madonna and Prince!

People in this episode

Host: Chris Gregory

Topics covered

• Bob Dylan
• 1980s pop music
• music commentary
• Minstrel Boy
• Dylan's career
• Michael Jackson
• Madonna

Keywords

• Bob Dylan
• 1980s
• pop songs
• Minstrel Boy
• Michael Jackson
• Madonna
• Prince
• music commentary

Mentioned in this episode

Books & works: Minstrel Boy

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• BOB DYLAN: A HEADFUL OF IDEAS Season Four 32) 'Pop Songs' of the 1980s (Part Three) · April 17, 2026 · 22 min
• BOB DYLAN: A HEADFUL OF IDEAS Season Four 30) 'Pop Songs' of the 1980s (Part One) · April 5, 2026 · 18 min
• BOB DYLAN: A HEADFUL OF IDEAS Season Four 29) Two Songs from 'Blood on the Tracks' · March 21, 2026 · 14 min

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