Can Bob Dylan be trusted? (with Elizabeth Cantalamessa)

Being a Bob Dylan fan is a spectrum –whether you identify as a casual enjoyer if his music or a die-hard Bobcat, the umbrella is large and leaves room for multitudes. 

Over the past year, many Definitely Dylan episodes have circled around the relationship between artist and audience, how Bob Dylan presents himself and how he is perceived. In the final conversation of 2025 (which you’re hearing in early 2026), we’re approaching this topic from a new angle.

My guest is Elizabeth Cantalamessa, an honest to god philosopher and one of the most fun people you can run into at a Bob Dylan show. We talk about Bob Dylan as the villain and trickster, selling out, and art as spiritual labour.

You can download the C. Thi Nguyen essay “Trust and Sincerity in Art” here.

Tiny correction:
The “Is there anything more American than America” wasn’t a Cadillac but a Chrysler commercial (watch it here). And btw, I’m burying this in the show notes because I’m not sure, but since we’re mentioning Lucy Sante at some point in this episode, I wanted to add that in her preface to Six Sermons for Bob Dylan (the book of sermons she wrote for the Trouble No More film), she mentions that she wrote a “Buick commercial” for him. As far as I’m aware, Dylan has never done a Buick commercial, unless you count the song “From a Buick 6”, so I’m wondering if she was maybe referring to this Chrysler commercial.

Bob Dylan and Santana - Toy Guns clip

Bob Dylan and Neil Young - “More of the same”

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