Roger Waters has never been one to hold his tongue. Whether it’s politics, music, or the state of the world, he speaks with the bluntness of a pub pundit who’s had just enough to drink. For Waters, silence is complicity—even when it comes to seemingly trivial matters like what kind of music his peers are making. He’s built his career on refusing to play nice, and if that means sounding cynical, so be it.
For a time, Bob Dylan was the archetype of artistic fearlessness Waters admires—an uncompromising voice holding up a mirror to society. As Led Zeppelin’s Robert Plant once put it: “Something happened when Dylan arrived. His music referenced Woody Guthrie, Reverend Gary Davis, Dave Van Ronk… He was absorbing the details of America and bringing it out without any reservation.” To Plant, Dylan was the man who introduced “reality” to rock and roll, inspiring him to ditch fashion and follow the message.
But in time, Dylan tired of being the spokesman for a generation. When fans turned into activists demanding he take up arms for their causes, he stepped back. He swapped protest songs for spiritual musings and, eventually, full-blown crooning. In 2015, Dylan released Shadows in the Night, a collection of old standards made famous by Frank Sinatra. Dylan defended it, saying: “We’re not covering these songs. We’re uncovering them. Lifting them out of the grave.”
Roger Waters didn’t buy it.
“I haven’t got time to do an album of Frank Sinatra covers like Bob Dylan, for instance,” he scoffed in one interview. “Which is weird. You go, ‘Fuck me, Bob, what is wrong with you? Why would you do that?’ I guess it’s because he can’t bear the thought of not being on the road and couldn’t think of anything else to do. I can’t believe he really has an affinity for all that schlock. But maybe he does.”
To be fair, Dylan’s desire to keep touring is well-documented. He once told Pete Townshend: “I’m a folk singer. A folk singer is only as good as his memory—and my memory is going.” Touring, for Dylan, may be less about vanity and more about survival. But that softer, sentimental side—the Sinatra side—has always been in him, even during his most cutting moments.
David Gilmour, Waters’ former Pink Floyd bandmate and longtime adversary, certainly thinks so. In an interview for Desert Island Discs, Gilmour chose Dylan’s ‘Ballad in Plain D’ as one of his all-time favorite songs. “I lived through a lot of his heavy protest stuff,” Gilmour said, “and this was another side I’m very keen on. This sort of love song approach.”
So while Waters saw Dylan’s turn toward torch songs as a betrayal of purpose, Gilmour saw it as proof of emotional range. The two men, once musical brothers, now illustrate two very different ways to interpret the legacy of one of music’s most enigmatic legends.
