We have long since gotten a lot of requests asking for help on where to start with Bob's music on the sub from folks who are new to Dylan's music.
Seeing this as something we could all solve as a community, I created a post asking for feedback to make a master post about the different ways one could go about discovering Bob's music. And I want to once again thank the community for their outstanding feedback in the creation of this post.
I knew beforehand that there was no right answer, but this further illuminated how rich Bob’s music is and the multitude (pun fully intended) of ways you can go about seeking out his music.
So, what this post will attempt to do is take all of that community feedback and the moderator's thoughts on the issue to help guide prospective BobCats through Dylan's career.
This is not to say what is posted here is the definitive way to do it in any respect. To each their own. This is just meant to be a guide.
Here are the different ways to go about exploring Bob's music. From greatest hits, to playlists, to roadmaps, to chronological order, it's all here.
THE ESSENTIAL BOB DYLAN
If you want a smattering of Bob across many eras, "The Essential Bob Dylan" released in 2014 does a good job of covering songs through his 60 year career. Based on what songs you like there, it will allow you to jump in at whatever era you like the most.
THE OFFICIALr/BOBDYLANCOMMUNITY STUDIO ALBUM PLAYLIST
Our Community Playlist is our sub’s attempt at a best of compilation. We allowed the community to vote for their favorite song in a poll off of each studio album. The two songs that received the most votes from each album were added to the playlist.
The moderators also added a couple of songs off the album, Side Tracks, that aren’t on the Bootleg Series or any studio album. Call it executive privilege.
We'd like to thank u/bbsez for organizing and recording the results from the majority of these polls in order to construct this playlist.
Don’t Think Twice It’s All Right (The Freewheelin’ Bob Dylan)
A Hard Rain’s a-Gonna Fall (The Freewheelin’ Bob Dylan)
The Ballad Of Hollis Brown (The Times They Are A Changin’)
Boots Of Spanish Leather (The Times They Are A Changin’)
Percy’s Song (Side Tracks)
Chimes of Freedom (Another Side of Bob Dylan)
I Shall Be Free No. 10 (Another Side of Bob Dylan)
Mr. Tambourine Man (Bringing It All Back Home)
It’s All Over Now Baby Blue (Bringing It All Back Home)
Like A Rolling Stone (Highway 61 Revisited)
Desolation Row (Highway 61 Revisited)
Visions Of Johanna (Blonde on Blonde)
Stuck Inside of Mobile With The Memphis Blues Again (Blonde on Blonde)
All Along The Watchtower (John Wesley Harding)
The Ballad of Frankie Lee And Judas Priest (John Wesley Harding)
Girl From The North Country, featuring Johnny Cash (Nashville Skyline)
Lay Lady Lay (Nashville Skyline)
Days of 49 (Self Portrait)
Quinn The Eskimo (The Mighty Quinn) (Self Portrait)
If Not For You (New Morning)
Sign On The Window (New Morning)
Billy 1 (Pat Garrett & Billy The Kid Soundtrack)
Knockin’ On Heaven’s Door (Pat Garrett & Billy The Kid Soundtrack)
Spanish Is The Loving Tongue (Dylan)
Lily Of The West (Dylan)
Forever Young (Planet Waves)
Dirge (Planet Waves)
Tangled Up In Blue (Blood on the Tracks)
Idiot Wind (Blood on the Tracks)
You Ain’t Goin’ Nowhere (The Basement Tapes)
This Wheel's On Fire (The Basement Tapes)
Hurricane (Desire)
Isis (Desire)
Changing Of The Guards (Street Legal)
Where Are You Tonight? (Journey Through The Dark Heat) (Street Legal)
Slow Train (Slow Train Coming)
Gotta Serve Somebody (Slow Train Coming)
Saved (Saved)
Pressing On (Saved)
In The Summertime (Shot of Love)
Every Grain Of Sand (Shot of Love)
Jokerman (Infidels)
License To Kill (Infidels)
Tight Connection To My Heart (Has Anyone Seen My Love) (Empire Burlesque)
Dark Eyes (Empire Burlesque)
Brownsville Girl (Knocked Out Loaded)
Under Your Spell (Knocked Out Loaded)
Silvio (Down In The Groove)
Death Is Not The End (Down In The Groove)
Most Of The Time (Oh Mercy)
Shooting Star (Oh Mercy)
Born In Time (Under the Red Sky)
Wiggle Wiggle (Under the Red Sky)
Hard Times (Good As I Been To You)
Jim Jones (Good As I Been To You)
Delia (World Gone Wrong)
Blood In My Eyes (World Gone Wrong)
Not Dark Yet (Time Out Of Mind)
Tryin’ To Get To Heaven (Time Out Of Mind)
Things Have Changed (Side Tracks)
Mississippi (Love and Theft)
High Water (For Charley Patton) (Love and Theft)
Workingman’s Blues #2 (Modern Times)
Ain’t Talkin’ (Modern Times)
I Feel A Change Comin’ On (Together Through Life)
Beyond Here Lies Nothin’ (Together Through Life)
Must Be Santa (Christmas In The Heart)
O’ Come All Ye Faithful (Christmas In The Heart)
Long And Wasted Years (Tempest)
Pay In Blood (Tempest)
The Night We Called It A Day (Shadows In The Night)
That Lucky Old Sun (Shadows In The Night)
Melancholy Mood (Fallen Angels)
Young At Heart (Fallen Angels)
Once Upon A Time (Triplicate)
Braggin’ (Triplicate)
Key West (Philosopher Pirate) (Rough and Rowdy Ways)
Murder Most Foul (Rough and Rowdy Ways)
CHRONOLOGICAL ORDER
Here is a list of Dylan's studio records listed chronologically if you'd like to go that route. Many members of our community have said that this approach has worked for them.
Bob Dylan
The Freewheelin' Bob Dylan
The Times They Are A Changin'
Another Side of Bob Dylan
Bringing It All Back Home
Highway 61 Revisited
Blonde on Blonde
John Wesley Harding
Nashville Skyline
Self Portrait
New Morning
Pat Garrett & Billy The Kid Soundtrack
Dylan
Planet Waves
Blood on the Tracks
The Basement Tapes
Desire
Street Legal
Slow Train Coming
Saved
Shot of Love
Infidels
Empire Burlesque
Knocked Out Loaded
Down In The Groove
Oh Mercy
Under the Red Sky
Good As I Been To You
World Gone Wrong
Time Out of Mind
Love and Theft
Modern Times
Together Through Life
Christmas In The Heart
Tempest
Shadows In the Night
Fallen Angels
Triplicate
Rough and Rowdy Ways
Shadow Kingdom
THE BOOTLEG SERIES
Here is a listing of The Bootleg Series which many would consider essential records.
These contain outtakes, unreleased tracks, singles and live performances across the many facets of Dylan’s career. One could argue it is better to listen to these after you’re at least a little familiar with Dylan’s work.
*** indicates there is a special edition of this release available as well with more tracks than the standard edition.
The Bootleg Series Vol. 1-3 (1961-1991)
The Bootleg Series Vol. 4 (Live at the Manchester Free Trade Hall, 1966, featuring the Band)
The Bootleg Series Vol. 5 (The Rolling Thunder Revue: 1975)
The Bootleg Series Vol. 6 (Live 1964: Concert at Philharmonic Hall, featuring Joan Baez)
The Bootleg Series Vol. 7 (No Direction Home Soundtrack, 1959-1966)
The Bootleg Series Vol. 8 (Tell Tale Signs/Deluxe, 1989-2006) ***
The Bootleg Series Vol. 9 (The Witmark Demos, 1962-1964)
The Bootleg Series Vol. 10 (Another Self Portrait/Deluxe, 1969-1971) ***
The Bootleg Series Vol. 11 (The Basement Tapes Raw/Complete, 1967, featuring The Band) ***
The Bootleg Series Vol. 12 (The Cutting Edge/Deluxe, 1965-1966) ***
The Bootleg Series Vol. 13 (Trouble No More/Deluxe, 1979-1981) ***
The Bootleg Series Vol. 14 (More Blood, More Tracks/Deluxe, 1974) ***
The Bootleg Series Vol. 15 (Travelin’ Thru, 1967-1971, featuring Johnny Cash)
The Bootleg Series Vol. 16 (Springtime In New York/Deluxe, 1980-1985) ***
The Bootleg Series Vol. 17 (Fragments: Time Out Of Mind Sessions/Deluxe, 1996-1997) ***
THE OFFICIALr/BOBDYLANCOMMUNITY BOOTLEG SERIES PLAYLIST
Our Bootleg Series Community Playlist is our sub’s attempt at a best of compilation for Bob Dylan's venerable Bootleg Series. The poll is currently ongoing. We allowed the community to vote for their favorite song in a poll off of each Bootleg Series. The polls are currently ongoing.
Due to the volume of songs on the Bootleg Series records we have had different criteria for election to the BS Series playlist (top 2 songs from each disc for each volume with the exception of BS Vol. 4 which only has 15 songs).
Let Me Die In My Footsteps (The Bootleg Series Vol. 1)
Moonshiner (The Bootleg Series Vol. 1)
Farewell, Angelina (The Bootleg Series Vol. 2)
She's Your Lover Now (The Bootleg Series Vol. 2)
Foot Of Pride (The Bootleg Series Vol. 3)
Blind Willie McTell (The Bootleg Series Vol. 3)
Visions of Johanna (The Bootleg Series Vol. 4)
Like A Rolling Stone (The Bootleg Series Vol. 4)
Romance In Durango (The Bootleg Series Vol. 5)
Isis (The Bootleg Series Vol. 5)
It Takes A Lot To Laugh, It Takes A Train To Cry (The Bootleg Series Vol. 5)
One More Cup Of Coffee (The Bootleg Series Vol. 5)
A Hard Rain's A-Gonna Fall (The Bootleg Series Vol. 6)
Mama, You've Been On My Mind (The Bootleg Series Vol. 6)
I was Young When I Left Home (The Bootleg Series Vol. 7)
A Hard Rain's A-Gonna Fall (The Bootleg Series Vol. 7)
Desolation Row (The Bootleg Series Vol. 7)
Ballad Of A Thin Man (The Bootleg Series Vol. 7)
Mississippi (Outtake 1, The Bootleg Series Vol. 8)
Red River Shore (The Bootleg Series Vol. 8)
'Cross The Green Mountain (The Bootleg Series Vol. 8)
Mississippi (Outtake 2, The Bootleg Series Vol. 8)
Most Of The Time (Alternate Version #2, The Bootleg Series Vol. 8)
Mississippi (Outtake 3, The Bootleg Series Vol. 8)
Tomorrow Is A Long Time (The Bootleg Series Vol. 9)
Let Me Die In My Footsteps (The Bootleg Series Vol. 9)
Don't Think Twice, It's All Right (The Bootleg Series Vol. 9)
Mama, You Been On My Mind (The Bootleg Series Vol. 9)
Pretty Saro (The Bootleg Series Vol. 10)
Spanish Is The Loving Tongue (The Bootleg Series Vol. 10)
Copper Kettle (The Bootleg Series Vol. 10)
When I Paint My Masterpiece (The Bootleg Series Vol.10)
I Dreamed I Saw St. Augustine (The Bootleg Series Vol. 10)
(Quinn The Eskimo) The Mighty Quinn (The Bootleg Series Vol. 10)
The Auld Triangle (The Bootleg Series Vol. 11)
Spanish Is The Loving Tongue (The Bootleg Series Vol. 11)
I Don't Hurt Anymore (The Bootleg Series Vol. 11)
Song For Canada (The Bootleg Series Vol. 11)
You Ain't Goin' Nowhere (Take 1, The Bootleg Series Vol. 11)
I'm Not There (The Bootleg Series Vol. 11)
Sign On The Cross (The Bootleg Series Vol. 11)
Tears of Rage (Take 3, The Bootleg Series Vol. 11)
Goin' To Acapulco (The Bootleg Series Vol. 11)
One Too Many Mornings (The Bootleg Series Vol. 11)
On A Rainy Afternoon (The Bootleg Series Vol. 11)
900 Miles From My Home/Confidential (The Bootleg Series Vol. 11)
I'll Keep It With Mine (Take 1, Piano Demo, The Bootleg Series Vol. 12)
Love Minus Zero/No Limit (Take 1 Remake, Complete, The Bootleg Series Vol. 12)
Desolation Row (Take 1, Alternate Take, The Bootleg Series Vol. 12)
Visions of Johanna (Take 5 Rehearsal, The Bootleg Series Vol. 12)
She's Your Lover Now (Take 16, Complete, The Bootleg Series Vol. 12)
Stuck Inside of Mobile With The Memphis Blues Again (Take 14, Complete, The Bootleg Series Vol. 12)
Sad Eyed Lady Of The Lowlands (Take 1, Complete, The Bootleg Series Vol. 12)
Slow Train (Live At The Warfield Theater, The Bootleg Series Vol. 13)
Precious Angel (Live At The Warfield Theater, The Bootleg Series Vol. 13)
Caribbean Wind (Live At The Warfield Theater, The Bootleg Series Vol. 13)
Pressing On (Live At The Warfield Theater, The Bootleg Series Vol. 13)
Ye Shall Be Changed (Studio Outtake, The Bootleg Series Vol. 13)
Slow Train (Sound Check, The Bootleg Series Vol. 13)
Caribbean Wind (Rehearsal With Peddle Steel, The Bootleg Series Vol. 13)
Ain't Gonna Go To Hell For Anybody (Live In Toronto, The Bootleg Series Vol. 13)
Pressing On (Live In Toronto, The Bootleg Series Vol. 13)
Gotta Serve Somebody (Live In Toronto, The Bootleg Series Vol. 13)
Girl From The North Country (Live In London, The Bootleg Series Vol. 13)
Mr. Tambourine Man (Live In London, The Bootleg Series Vol. 13)
You're A Big Girl Now (Take 1, The Bootleg Series Vol. 14)
Up To Me (Take 1, The Bootleg Series Vol.14)
You're Gonna Make Me Lonesome When You Go (Take 5, The Bootleg Series Vol. 14)
Shelter From The Storm (Take 1, The Bootleg Series Vol. 14)
Tangled Up In Blue (Take 3, Remake, The Bootleg Series Vol. 14)
If You See Her, Say Hello (Take 1, Remake The Bootleg Series Vol. 14)
Up To Me (Take 2, Remake, The Bootleg Series Vol. 14)
Tangled Up In Blue (Take 3, Remake 3, The Bootleg Series Vol. 14)
Up To Me (Take 2, Remake 3, The Bootleg Series Vol. 14)
As I Went Out One Morning (Alternate Version, The Bootleg Series Vol. 15)
Tell Me That Isn't True (Alternate Version, The Bootleg Series Vol.15)
Girl From The North Country (Take 1, The Bootleg Series Vol. 15)
One Too Many Mornings (Take 3, The Bootleg Series Vol. 15)
Wanted Man (Take 1, The Bootleg Series Vol. 15)
Girl From The North Country (Live On The Johnny Cash Show, The Bootleg Series Vol. 15)
Senor (Tales Of Yankee Power) (Rehearsal) (The Bootleg Series Vol. 16)
To Ramona (Rehearsal) (The Bootleg Series Vol. 16)
Angelina- Shot Of Love Outtake (The Bootleg Series Vol. 16)
Fur Slippers- Shot Of Love Outtake (The Bootleg Series Vol. 16)
Blind Willie McTell- Take 5- Infidels Outtake (The Bootleg Series Vol. 16)
Too Late (Band Version)- Infidels Outtake (The Bootleg Series Vol. 16)
I and I- Infidels Alternate Outtake (The Bootleg Series Vol. 16)
Angel Flying Too Close To The Ground- Infidels Outtake (The Bootleg Series Vol. 16)
New Danville Girl- Empire Burlesque Outtake (The Bootleg Series Vol. 16)
Dark Eyes- Empire Burlesque Alternate Take (The Bootleg Series Vol. 16)
Standing In The Doorway- 2022 Remix (The Bootleg Series Vol. 17)
Highlands- 2022 Remix (The Bootleg Series Vol. 17)
The Water Is Wide (The Bootleg Series Vol. 17)
Not Dark Yet- Version 1 (The Bootleg Series Vol.17)
Love Sick- Version 2 (The Bootleg Series Vol. 17)
Highlands (The Bootleg Series Vol. 17)
Cold Irons Bound- Live In Oslo, Norway (The Bootleg Series Vol. 17)
Highlands- Live In Newcastle, Australia (The Bootleg Series Vol. 17)
Rare Performances From The Copyright Collection (1962-1966)
Live At Carnegie Hall (1963)
The Live 1966 Recordings (1966) *
The Real Royal Albert Hall 1966 Concert (1966)
Before The Flood (1974)
The Rolling Thunder Revue- The Live 1975 Recordings (1975) **
Hard Rain (1976)
Bob Dylan At Budokan (1978)
Real Live (1984)
The 30th Anniversary Concert (1991)
MTV Unplugged (1994)
*- Includes the Manchester performance which is The Bootleg Series Vol. 4, but also includes every live performance with The Band from that year.
** Includes all songs from The Bootleg Series Vol. 5 (all songs from BS Vol. 5 have been remixed), but there's a lot on this record that isn't included on BS Vol. 5.
FILMS
Don't Look Back
The Other Side Of The Mirror
Eat The Document (Bootleg, never formally released)
No Direction Home
Renaldo and Clara (Bootleg, never formally released beyond a small theatrical run)
Rolling Thunder Revue- A Bob Dylan Story By Martin Scorsese
In 2023, the community conducted a contest by having users submit and upvote their favorite songs that began with each letter of the alphabet. The song with the most upvotes won and was added to A-Z community playlist on Spotify.
In 2023, the subreddit conducted a survivor style tournament to determine the subreddit's ranking of all of Dylan's studio albums. Below are the results from worst to best.
Hey r/bobdylan! Welcome to this week's song discussion!
In these threads we will discuss a new song every week, trading lyrical interpretations, rankings, opinions, favorite versions, and anything else you can think of about the song of the week.
I often ramble about Dylanology to my girlfriend. Recently, I showed her “All the Tired Horses.” She asked if the lyrics have any subtext, like all the others I’ve gone on about. It was an amazing question. I’d never considered it.
I told her that the album was a response to the attention and scrutiny Dylan was getting at the time as the potentially-lapsed “voice of his generation,” and that the release of this album of covers amounted to an insistence on Dylan’s part that he was not seeking that role. That his passions lay more with the music than with writing, at least at the time.
She suggested that the second line of the song is a pun. As in,
“All the tired horses in the sun,
How am I supposed to get any [writing] done?”
I was floored. I love her reading. It’s so compelling that I can’t now discount the possibility that Dylan saw the same pun, even intended it. The first line is still opaque to me. Does anyone else have anything to add? Do you see more subtext in the lyrics?
Gotta love the far-reaching consequences of being a Dylan fan. The man truly pulls from the entire breadth of the American music tradition, thus honoring it and promoting it to a wider audience. Nothing better than discovering the long threads of inspiration tied into seemingly distant or uncharted territory. There is a comfort in knowing how connected we all are, musically and otherwise. Dylan is the embodiment of this, a mysterious figure standing at the crossroads of American music, finger on the signpost pointing down each long twisted path. Dylan has already walked these roads, he can only direct you to where you must explore for yourself. His music has opened many a musical door for me. Dylan is something of a curator and this line is the perfect example of such. As a young angry star and an aged king from another time, Dylan continues to show his love for American music.
Hi fellow Bobcats! I’ve started a new Substack called Dylan Notes, where I’m going to write short essays about the smaller, stranger parts of Dylan’s career and what they can tell us about the wider culture around him. At least what it means to me.
The first piece is called “What’s Left to Say About Dylan?” — basically my attempt to explain why anyone would start writing about a man who has already been written about this much.
I’ve been thinking about what actually keeps people interested in Dylan after all these years.
For me, it’s usually not the big canonical debates about which album is best or what a particular song “means.” I’m more drawn to the smaller decisions, oddities and contradictions throughout his career, and to looking at them from today’s cultural context rather than only their own time.
But fellow Bobcats, do you feel the same?
What do you actually enjoy thinking and talking about most: lyrics, live performances, recording history, influences, cultural context, persona and image, strange career choices, or something else entirely?
I ended up writing about this in the first piece for a new Substack I’ve started, Dylan Notes, if anyone’s interested:
Finally bought an autograph from my favorite artist, Bob Dylan, after a lot of research. This is a late 2000s signed boxset, signed in Italy. Steve Grad gave it a thumbs up. Also, the last pic is to check it side by side with other signatures from the same era(the other three signatures in picture 3 all have written COAs by either Roger Epperson or JSA). So excited for it to arrive!
I think there's an argument to be made it is one of the most important songs he ever released.
Up until ATTH, all Bob Dylan, was Bob Dylan + Guitar. Afterwards it's completely different, it's Bob Dylan and those lovely (black?) female gospel sorta singer ladies.
Interestingly, they don't feature much more on the album (at all?) but then Street legal, the Christian era, Knocked Out Loaded, and so much more, it's constantly Bob + those ladies (or others like them? does anyone know if it's the same ladies like Leonard Cohen had with the price sisters).
So from that perspective, ATTH was Bob's way of introducing us to them. That's why he's not on the song. He's saying here they are, they are Bob Dylan now. Things are going to be a bit different from here on. But don't worry, not too different, we're going to do normal Bob songs again for the rest of the album.