Have you seen A Complete Unknown starring Timothée Chalamet as Bob Dylan? Released at the end of 2024, the film has inspired a renewed interest in the music and story of Bob Dylan’s early days in New York.
With the release of the movie, The Bowery Boys New York History Podcast released an episode, “Bob Dylan’s Greenwich Village: The Neighborhood Which Shaped American Music”, and Bowery Boys Walks launched a new Bob Dylan walking tour soon after, led by tour guide Ann McDermott.
Ann took some time out of her busy tour schedule to talk all things Dylan and how she was inspired to create a special tour about this music legend.

How long have you been a Bob Dylan fan, and what makes his music so special?
My older brother introduced me to Bob Dylan in the early 1960s. He loved his lyrics and catchy melodies.
What was your journey to becoming a Bob Dylan tour guide?
The first tour I wrote was about the East Village music scene of the 1970s, and it ended at my favorite club, The Bottom Line at Mercer and 4th Street. On one of the first tours, I had a guest who said “Oh, I used to work for the man who ran the Bottom Line, Allan Pepper”, she was his babysitter. I was blown away! She actually introduced me to him, and he told me he used to work as a booker at Gerde’s Folk City. I knew of Folk City on 3rd Street, but didn’t realize it used to be on the opposite corner from The Bottom Line. Every time I ended that tour, I knew there was a whole other story to tell about the West Village, where the folk revolution had happened. So, I started reading and doing research, and the result is the tour I do today.

What did you think of the movie A Complete Unknown? And how do you think it opened up Bob Dylan to new fans and renewed interest for longtime ones?
I loved A Complete Unknown. I thought it did a great job telling Dylan’’s story in broad strokes and included most of the characters who were involved in helping him get his start. Funny thing, I was doing this tour in the Spring of 2024, and every place I went had signs that said they were filming a movie. I knew it was the Dylan movie even though the signs had another title. Then, of course, the movie was filmed in New Jersey, but the story and the music are spot on. Almost everyone who comes on the tour today has seen the movie, including the younger people who seem very curious about how Bob (and others) got started here in Greenwich Village.

How did you develop the tour and decide where to stop in the neighborhood?
Well, the starting point was easy! The first place Bob had his name in the Village Voice, Gerde’s Folk City on Mercer and 4th, the rest just flowed naturally, Washington Square Park, Bleecker Street, MacDougal Street, the nexus of the Folk Music World in the 1960s. Then there are other sort of “off the beaten path” stops that aren’t far away that add to his story.
What is one of the highlights of the tour for you?
A few weeks ago, I had a very nice family from overseas taking the tour. The husband was extremely engaged and enthusiastic about all the stops and took a lot of photos along the way. When we got to the Hotel Earle (now called the Washington Square Hotel), he started crying. He said, “I’ve been listening to that song (Diamonds and Rust) since I was in High School, and here it is ‘that crummy hotel over Washington Square’”. It reminded me of how I felt when I visited Paul McCartney’s home in Liverpool — to be in the place where the people we loved created the music that changed our lives forever. The whole experience was extremely meaningful!
Finally, what are you top 3 Bob Dylan songs?
1) Tangled Up in Blue – love that melody!
2) Mr. Tambourine Man – because I can actually play it on the guitar
3) Blowin’ in the Wind – what child of the ’60s doesn’t love that one!
Thanks, Ann!
Take a trip to Greenwich Village to see where Bob Dylan got his start!