What we’re looking at here is less a missed opportunity, and more a tragic inevitability. The stars almost aligned — almost — for a historic collaboration between two of the most transformative forces in popular music. But despite what could’ve been one of the most culturally seismic musical duets of all time, it didn’t materialise. And knowing what we now know, it likely never could.
David Bowie, ever the artful chameleon, was transparent in his admiration for Bob Dylan. His 1971 track Song for Bob Dylan wasn’t just a tribute — it was a mission statement. Speaking five years later, Bowie said: “That laid out what I wanted to do in rock... I said, ‘okay (Dylan) if you don’t want to do it, I will.’” This wasn’t flattery. It was a declaration — Bowie saw a vacuum where vision and innovation should have been, and felt compelled to fill it.
By the time the pair were both cultural institutions rather than rising stars, a collaboration was briefly on the table. Talking to Marc Riley in 2004, Bowie revealed: “Me and Dylan, we were going to do a duet thing at one time... we got it in our heads that we could do it a duet, like a Simon & Garfunkel thing, but in the next morning, I didn’t hear another word from him.”
Bowie, while disappointed, seemed to accept Dylan’s withdrawal with a mixture of reverence and resignation. “I feel that frankly over the last 20 years or so I’m pretty much my own man... but if I look at Bob Dylan, he doesn’t have competition... he is just Bob Dylan.”
He likened Dylan’s cultural singularity to that of the Rolling Stones: untouchable, unmatchable, not even in the conversation with their supposed “competitors.” In short, Bowie knew greatness when he saw it — even if it didn’t exactly return his calls.
And perhaps therein lay the issue. While Bowie admired Dylan from a creative distance, their personal dynamic was, at best, mismatched. Speaking to Playboy in 1976, Bowie recalled their one-on-one encounter: “We didn’t have a lot to talk about... I think he hates me.”
He described a night of one-sided conversation, where Dylan offered little more than stoic silence. Bowie, uncharacteristically unsure of himself, was left questioning whether he’d amused, terrified, or outright alienated the man he so admired.
Still, Bowie honoured Dylan in the way only Bowie could — not with a forced or awkward collaboration, but through reinvention. He covered Like a Rolling Stone with Mick Ronson, and recorded a demo of Tryin’ to Get to Heaven with Tony Visconti — released posthumously in 2021.
It’s the closest we’ll ever get to hearing what that partnership might’ve sounded like. And given the egos, styles, and creative temperaments involved, maybe that’s for the best. A moment in time that almost happened. And now, can never be undone.
