When Tom Waits taught Bob Dylan Jewish swear words on the radio

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Bob Dylan and Tom Waits: the beloved buddies who mailed each other cassette messages

Thu 9 April 2026 18:30, UK

Like two lovers torn apart during wartime, Bob Dylan and Tom Waits have an intrinsic connection that has to take up a physical space in the world.

Don’t get things twisted with any ludicrous fantasies – it’s not like that. But the fact remains that out of all the great American songwriters who are still here to tell the tale, Dylan and Waits are indisputably two of the best to ever do it. Their shared language is most definitely songs, because when holding a conversation becomes too difficult, lyrics can always convey exactly what they want to say.

That’s a rather expressive way of essentially saying that the pair worship the ground each other walk on as writers, and it’s not without good reason. Indeed, Waits once said of his counterpart: “Suffice it to say Dylan is a planet to be explored. For a songwriter, Dylan is as essential as a hammer and nails and a saw are to a carpenter.” Put simply, the man sees him not just as a friend, but as integral to his life as oxygen.

Yet what happens with two wordsmiths when they come into each other’s orbits is that they start putting their heads together. Honestly, it’s more dangerous than it sounds. And thus, when Dylan had a stint as a radio DJ on SiriusXM, he pulled Waits into his world of whimsy not for any particular reason other than to have a bit of fun.

The pair would pretend that they were in the habit of sending each other cassette messages, during which Waits would often come up with any given kind of fantastical story to add to the entertainment value of Dylan’s show. Yet when this seemingly throwaway segment began to attract somewhat of a cult following, their web of fantasy only had to keep growing bigger.

It’s hardly surprising to hear Waits say that he likes his music with “the rinds and the seeds and pulp left in,” which is the exact embodiment of what Dylan and his body of work has come to symbolise. “His journey as a songwriter is the stuff of myth, because he lives within the ether of the songs,” Waits added, but it’s then that you realise what attracts them together so much. They’re singing from the same hymn sheet.

Even though the cassette messages may have been a figment of the imagination, there’s no losing sight of the fact that it was the product of two men who know how powerful they are to each other, let alone to the industry at large. People would come flocking to hear them read the phone book, and so if they were able to have a little fun with it, it was certainly worth a shot.

There have been plenty of connections which have kept the pair’s bond strong over the years, between the fictional tape messages to the album cover for Waits’s 1992 album Bone Machine being photographed by Dylan’s son, Jesse. Ever since they met in the 1970s, they realised they had kindred spirits in one another – and have never let that go.

Essentially, the cassette messages were nothing more than some mates mucking around, except with a rather sizeable and pining audience being interested in every word they were saying. It’s not often that conversations between a pair of middle-aged men become the centre of the universe – but when they have one hell of an imagination on them, it suddenly means everything.