Bob Dylan And the Blues: Top 15 Songs

In 1959, Bob Dylan recorded his 12-bar blues “When I Got Troubles”. This track from “No Direction Home – Bootleg 7” was one of his earliest compositions. It conveyed a feeling similar to ‘”The Trouble Blues” by Lightnin’ Hopkins, one of the greatest blues creators of all time. While Dylan has never been a purely blues musician, he was a bluesman from the start.

A few months after the recording, Dylan was already experimenting with the urban humorous talking blues, and his “Song for Woodie”, which closely followed “When I Got Troubles”, was not a blues song at all. While he definitely meandered away from the genre, it still influenced him in many ways. Bob Dylan’s legacy reflects the influence of blues in its many shapes, from jazz blues to folk blues to swing blues. Here is a look at some of his songs with the strongest blues overtones.

Our Playlist

Bob Dylan has played blues or blues-tinted songs throughout his career.  Listen to these tracks while playing at and see for yourself! This is a great playlist for a rainy day.

  1. Highway 51 Blues
  2. Poor Boy Blues
  3. Hero Blues
  4. Cocaine Blues
  5. Just Like Tom Thumb’s Blues
  6. Bob Dylan’s Blues
  7. Call Letter Blues
  8. Lonesome Day Blues
  9. Black Crow Blues
  10. Subterranean Homesick Blues
  11. When I Got Troubles
  12. Man in the Street
  13. I Was Young When I Left Home
  14. Ballad for a Friend
  15. Standing on the Highway

The Drive for Experimentation

From the very start, Dylan experimented like a madman. Talking blues presents the singer’s troubles as a joke, while the classic type lists more troubles than the listener can imagine, and uses line repetition to emphasize their severity. Dylan’s first real 12-bar blues is probably Hero Blues recorded in 1963.

Dylan played around with both the subgenres and the form. His “Man on the Street” is a peculiar fusion of blues and folk. While the subject matter is death in poverty, the music strays away from the three chords and 12 bars. Dylan was interested in blending different forms. In his first years of composing, he was a classic blues man, a folk singer, and a comedian at the same time. “I Was Young When I Left Home” is a great example.

In 1962, he was clearly into blues, but his one-chord “Poor Boy Blues” is still not a 12-chord classic. Dylan has never been keen on the constraints of the classic form. Instead, he was always taking the blues somewhere else. His “Ballad for a Friend” is a story of death and the railroad track, but it is not a 12-bar blues song, either. Despite the format of its lyrics, “Standing on the Highway” shows the same experimentation with the form.

This passion for musical innovation reflects the enormity of his talent. He has always enjoyed travelling in multiple directions. While Dylan has never been keen on pure blues, many of his songs are clearly influenced by it.

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