As I was starting my reaction channel, my husband recommended a list of songs, and among them was Dylan’s “Masters of War.” A track so thought-provoking and well written that, when I first heard it, I thought, “Wow. What a wise old man.”
On further exploration, I learned this was actually Bob at the very beginning of his career.
You might think I decided to listen to his entire catalogue simply because I was impressed by that discovery. The answer is, well, yes… and not exactly.
I was actually just as impressed by the listeners of Dylan and the quality of the comments they left on my videos. So thoughtful, so layered, so deeply engaged that I became hellbent on discovering what kind of musician could draw in listeners like that.
This has been true for most of the artists I’ve chosen to explore. The listeners have been my gateway to the music. They are the reason I go further. For me, they reflect fragments of an artist that I may never meet in the flesh.
In 2025, the journey began: a deep exploration into Bob Dylan’s music. I am by no means a Dylan scholar, nor do I claim perfect interpretations. But I have been having a lovely time witnessing his evolution and slowly becoming more competent at understanding his lines.
As he so clearly expressed in the San Francisco press conference, when we hear a word, we all picture something different. Who can say what is the right or wrong way to interpret a song? As he puts it, in some way, they are all simply “Good luck, and I hope you make it.”
That has become my north star in understanding and appreciating his music.
Below is the roadmap of my journey so far. If you’d like to follow along in real time, you can find me on YouTube and Patreon.
Note: These tables aren’t perfect, but I’ll add items as we progress.
Bob Dylan Deep Dive: Structured Chronological Archive
PHASE I: The Voice of a Generation (1962–1964)
| Year | Title | Type | Notes | My Reaction |
|---|---|---|---|---|
| 1962 | Bob Dylan | Album | Debut studio album | Watch on YouTube |
| 1962 | Gaslight Café Tapes | Live | Early Greenwich Village recordings | Coming Soon |
| 1962 | Broadside Sessions | Demo Sessions | Early political demos | Coming Soon |
| 1963 | The Freewheelin’ Bob Dylan | Album | Breakthrough songwriting record | Watch on YouTube |
| 1963 | Studs Terkel Interview | Interview | Early radio interview | Coming Soon |
| 1963 | March on Washington Speech | Speech | Civil rights appearance | Coming Soon |
| 1963 | Tom Paine Award Speech | Speech | Watch on YouTube | |
| 1963 | Let Me Die In My Footsteps | Outtake | Freewheelin’ outtake | Coming Soon |
| 1963 | Talkin’ John Birch Paranoid Blues | Outtake | Controversial TV pulled performance | Watch on YouTube |
| 1963 | Percy’s Song | Outtake | Long narrative ballad | Coming Soon |
| 1963 | Seven Curses | Outtake | Times era outtake | Coming Soon |
| 1964 | The Times They Are A-Changin’ | Album | Stark protest record | Watch on Youtube |
| 1964 | Another Side of Bob Dylan | Album | Turn toward personal lyricism | Watch on Youtube |
| 1964 | Newport ’64 – Mr. Tambourine Man | Live | First major folk festival shift | Coming Soon |
| 1964 | Mama, You Been On My Mind | Outtake | Another Side session | Watch on YouTube |
| 1964 | Farewell Angelina | Outtake | Early surreal lyricism | Watch on Patreon |
PHASE II: Going Electric (1965–1966)
| Year | Title | Type | Notes | My Reaction |
|---|---|---|---|---|
| 1965 | Bringing It All Back Home | Album | Acoustic / electric split | Watch on Youtube |
| 1965 | Subterranean Homesick Blues Film | Short Film | Early proto-music video | Coming Soon |
| 1965 | Highway 61 Revisited | Album | Electric landmark | Watch on YouTube Patreon Uncut |
| 1965 | KQED Press Conference | Interview | Iconic press confrontation | Watch on Patreon |
| 1965 | Don’t Look Back | Documentary | UK tour documentary | Watch on Patreon |
| 1966 | Blonde on Blonde | Album | First double rock LP | Watch on YouTube Patreon Uncut |
| 1966 | May Fair Hotel Press Conference | Interview | London press | Coming Soon |
| 1966 | Manchester “Judas” Concert | Live | Legendary electric confrontation | Coming Soon |
| 1966 | Eat the Document | Tour Film | Experimental tour footage | Coming Soon |
| 1966 | I’ll Keep It With Mine | Outtake | Blonde on Blonde era | Watch on Patreon |
PHASE III: Retreat? (1967–1974)
| Year | Title | Type | Notes | My Reaction |
|---|---|---|---|---|
| 1967 | John Wesley Harding | Album | Sparse Biblical minimalism | Coming Soon |
| 1967 | Basement Tapes (Original Sessions) | Sessions | Big Pink recordings with The Band | Coming Soon |
| 1969 | Nashville Skyline | Album | Country pivot | Coming Soon |
| 1969 | Girl From the North Country (with Johnny Cash) | TV Performance | Nashville Skyline duet | Coming Soon |
| 1970 | Self Portrait | Album | Polarizing double album | Coming Soon |
| 1970 | New Morning | Album | Quick creative rebound | Coming Soon |
| 1973 | Pat Garrett & Billy the Kid | Soundtrack | Includes Knockin’ on Heaven’s Door | Coming Soon |
| 1974 | Planet Waves | Album | Reunion with The Band | Coming Soon |
| 1974 | Before the Flood | Live | 1974 comeback tour | Coming Soon |
PHASE IV: ??? (1975–1981)
| Year | Title | Type | Notes | My Reaction |
|---|---|---|---|---|
| 1975 | Blood on the Tracks | Album | Divorce era masterpiece | Coming Soon |
| 1975 | Abandoned Love | Outtake | Blood on the Tracks era | Coming Soon |
| 1975 | Desire | Album | Cinematic storytelling | Coming Soon |
| 1975 | Rolling Thunder Revue | Tour | Masked theatrical era | Coming Soon |
| 1976 | Hard Rain | Live | Rolling Thunder broadcast | Coming Soon |
| 1979 | Slow Train Coming | Album | Beginning of gospel trilogy | Coming Soon |
| 1979 | Ye Shall Be Changed | Outtake | Gospel era rehearsal | Coming Soon |
| 1980 | Saved | Album | Gospel period | Coming Soon |
| 1981 | Shot of Love | Album | Final gospel phase | Coming Soon |
PHASE V: ??? (1983–1997)
| Year | Title | Type | Notes | My Reaction |
|---|---|---|---|---|
| 1983 | Infidels | Album | Secular return | Coming Soon |
| 1983 | Blind Willie McTell | Outtake | Legendary Infidels outtake | Coming Soon |
| 1989 | Oh Mercy | Album | Daniel Lanois collaboration | Coming Soon |
| 1989 | Series of Dreams | Outtake | Oh Mercy sessions | Coming Soon |
| 1992 | Good as I Been to You | Coming Soon | ||
| 1993 | World Gone Wrong | Coming Soon | ||
| 1995 | MTV Unplugged | Live | Acoustic retrospective | Coming Soon |
| 1997 | Time Out of Mind | Album | Late-career renaissance | Coming Soon |
| 1997 | Red River Shore | Outtake | TOOM sessions | Coming Soon |
| 1997 | Mississippi (Early Versions) | Outtake | TOOM era | Coming Soon |
PHASE VI: ??? (2001–Present)
| Year | Title | Type | Notes | My Reaction |
|---|---|---|---|---|
| 2001 | Love and Theft | Album | Postmodern blues collage | Coming Soon |
| 2004 | Chronicles Vol. 1 | Book | Autobiography | Coming Soon |
| 2005 | No Direction Home | Documentary | Scorsese film | Coming Soon |
| 2006 | Modern Times | Album | Blues traditionalism | Coming Soon |
| 2012 | Tempest | Album | Titanic meditation | Coming Soon |
| 2015 | Shadows in the Night | Coming Soon | ||
| 2016 | Fallen Angels | Coming Soon | ||
| 2017 | Triplicate | Coming Soon | ||
| 2017 | Nobel Prize Lecture | Speech | Literary reflection | Coming Soon |
| 2020 | Rough and Rowdy Ways | Album | Late career philosophical record | Coming Soon |
| 2023 | Shadow Kingdom | Album / Film | Reimagined classics | Coming Soon |
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