10 · 09 · 2025
Bob Dylan and Tom Waits are two of the most legendary figures in modern music, both songwriters possessing exceptional depth and longevity. Over the years, they have encountered each other numerous times—indeed, a series of coincidences connect these iconic American artists.
One of the most notable connections is that the striking and unusual cover photograph for Tom Waits’ album ‘Bone Machine’ was captured by Jesse Dylan—Bob’s son, who is also a talented visual artist.
The two songwriters share a long history. For example, there’s an anecdote—possibly apocryphal—that when Bob Dylan and Tom Waits first met in the mid-70s, Dylan instantly mimicked Waits' distinctive growl. Additionally, there’s a story told by Jakub Dylan about how Tom Waits was visibly nervous during their first meeting.
When Bob Dylan received the Nobel Prize for Literature in 2016, Waits referred to him as a “master”. He elaborated, saying: “It’s a great day for Literature and for Bob when a Master of its original form is honored. Before epic stories and poems were ever documented, they traveled on the winds of the human voice, and no voice is greater than Dylan’s.”
The two have never recorded together, yet both have shared airtime during Bob Dylan's tenure as a host on SiriusXM. The Bard’s iconic Theme Time Radio Hour included many memorable moments, featuring a surreal recurring guest appearance from Tom Waits.
The two engaged with the audience, humorously telling listeners that they exchanged audio cassettes with one another. During the show, Bob Dylan would introduce a topic, then ‘retrieve’ a message from Tom Waits—often filled with whimsical ideas.
These segments have garnered a cult following of their own—listen to those one-of-a-kind audio snippets below.
Related: Tom Waits’ Wisdom on Living a Fulfilled Life Remains Relevant
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Bob Dylan and Tom Waits are among the most legendary figures in contemporary music, renowned for their profound and enduring songwriting. The two have encountered each other on multiple occasions.
