This “Mystical” Bob Dylan Track Was Inspired by Caribbean Folklore (And Dylan’s Lesser-Known Hobby in the 1980s)

When one thinks of a musician lounging in the tropical sunshine on the teak deck of a gorgeous, custom-built schooner, one might think of artists with sunnier dispositions like Jimmy Buffett, Brian Wilson, or virtually any of today’s current pop stars who spend their vacations in luxurious, oceanic settings. The musician most of us would not think of is the reserved, opaque, and constantly furrowed-brow singer-songwriter icon, Bob Dylan.

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But then again, that just goes to show how little the general public really knows about the man formerly known as Robert Zimmerman.

Bob Dylan Began Cruising the Caribbean in the 1980s

Public speculation and critique have followed Bob Dylan throughout his entire career. From his transition out of the sociopolitical protest arena to his decision to go electric to his later decision to go Christian, Dylan has built his entire legacy on doing the exact opposite of whatever the masses think he’ll do. A perfect example was the investment hobby he took up in the early 1980s: sailing in the Caribbean on a custom-built schooner called the Water Pearl.

Dylan tended his ship alongside his captain, Charles Bowman, who became his partner after the original business deal pertaining to the custom-built ship fell through. Both men enjoyed a successful partnership. Bowman used the ship as a charter boat, and Dylan would come down when he could, soaking in the sunshine, peace, and quiet that the Caribbean waters provided.

In 1988, Water Pearl sank after striking a reef in the Panama Canal. According to Bowman, Dylan said of the incident, “Man, it’s like that reef has been sitting there waiting for you since the very beginning.” That was the sad, unfortunate end to Water Pearl. But memories of the impressive schooner weren’t the only things Dylan took from his time in the Caribbean.

How the Islands Helped Inspire This Mark Knopfler-Produced Track

Bob Dylan released Infidels in 1984, something many historians cite as the official end of his born-again Christian era. The singer-songwriter employed Dire Straits frontman Mark Knopfler to produce the album, which was as successful as it was occasionally tense. The third single from the album, “Jokerman”, came from Dylan’s travels throughout the Caribbean.

Speaking to Rolling Stone in 1984, Dylan said that “Jokerman” had “came to me in the islands. It’s very mystical. The shapes there, and shadows, seem to be so ancient. The song was sorta inspired by these spirits they call jumbis.” Jumbis are mythological creatures common in English-speaking Caribbean states. They are typically associated with dark, demonic energy.

The same kind of spirits that would lead a schooner to its watery grave.

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