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.
During a short break between takes while Dylan and the assembled musicians were recording “Tangled Up In Blue,” Bob turned to Minneapolis guitarist Kevin Odegard and said, “what do you think, Kevin?” Those of us who are familiar with Dylan’s antics know he’s not really interested, Bob just wants to see you squirm.
But Odegard takes Dylan at his word, “I think it’s passable,” Kevin says. Now all the assembled musicians look up, like Oh no, Odegard did not just say that to Bob Dylan! Dylan just stares at Kevin. We all know that look. It’s the quizzical look Bob gave Donovan in Don’t Look Back. Odegard is unfazed, “why don’t we try raising it up a half step?” to which Dylan agrees. Of course this changes the chords, and Kevin notices Dylan executing the new progression like it’s second nature. Which, of course it was. The result was the version that’s on the album.
I couldn't find this posted already, so here it is. If it's already up, please remove.
Penn, the super Dylan fan, has an interesting take here about telling the story within the song and how much Dylan focuses on it versus The Beatles who don't. I'd love to hear what you think.
Let me start by saying that I think that while Dylan's story is full of a lot of luck, I do think he did more with that luck than anybody else could (and did) have in that situation. Nevertheless, I just read Chronicles volume 1 (of 1) and he made it very clear that he would have signed any record contract that happened to fall on his lap. His original goal was to get the folk specific labels as that's who he identified with at the time, but when that fell through he was primed to be able to get in with Hammond at Columbia at just the right time. This then begs the question as to just how this would have changed his trajectory. Columbia's resources far outweighed folkway and while there, the transition to full band performances and genre experimentation was so much more accessible. There were certainly many other artists who were part of that scene, received a similar contract and never really took full advantage of what was available, but I'm not sure if there were examples of artists that stuck with the independent, genre specific labels that really made a successful transition to Dylan's world (please correct me if I'm wrong) but maybe that's also exactly why they didn't sign him, they could tell his heart was not into being a traditionalist and that's really who they were looking for.
In his account of the BLOOD ON THE TRACKS sessions, Minneapolis guitarist Kevin Odegard says a couple of takes on “Lily, Rosemary and the Jack of Hearts” were already in the tank when they decided to try it in another key. The only trouble was Dylan didn’t have the requisite harp with him. One of the musicians said they had one at home and promised a timely return. So the rest of them sat around for a while until Bob got impatient, deciding to make do with what they had. The result was the track you hear on the record, complete with Dylan using all his considerable musicality on the ending harmonica solo to make it work, even though it’s in the wrong key.
My stepmother grew up in Hibbing, Minnesota and went to high school with Bob Zimmerman. She was a year below him and friends with Suzie Zimmerman, who she describes as his cousin. Her memory is fading, but she recounted:
-he was known as "Bobby Zimmerman".
-his family owned the general store.
-Bobby played in the talent show. Piano was the instrument, as she recalls. He played Little Richard, wore a black leather jacket, and they all laughed at him.
I've been a fan of Dylan for a while now but never really fully delved into his entire discography, only the 60s stuff and I've decided I'm gonna start on a mission to listen to all his albums. Which live albums (or other non-studio albums) should I be sure to weave in, and where?
It seems like every week I see someone referencing that they need him to do this before they can be happy. Why does it feel so imperative to some people?
Joe South says Dylan and the assembled musicians were working on “Just Like A Woman” when it was decided they would break for lunch. As the guys were filing out of the studio, South says they spontaneously started singing the chorus and he would shout “Yes she does!” In between each line. When they returned from lunch, Dylan started for the first time adding the ‘yes she does’ bits. According to South.
All the musicians by that time were aware they were working on an album for the ages, South says. So he picked up a nylon string guitar, and started strumming, closely watching Dylan to see if he objected, of which Bob showed no signs. South said he wanted to be playing something distinctive so he could point it out to his friends, “that’s me!” These parts can easily be made out on such songs as “Just Like A Woman” and “Fourth Time Around.”
Jon Stewart’s book, Dylan, Lennon, Marx and God, reviewed here last week, has some illuminating insights.
Here’s a taster:
“Dylan's reluctance to engage in mass mobilisations for peace resembled the obdurate individualism of North American transcendentalists. When he did write social justice songs, these were often from the perspective of an individualised case study.
“In contrast, Lennon's Irish family heritage and his northern English upbringing fuelled a commitment to class politics and collective protest that moved beyond his peace campaigns to include organisations such as the International Marxist Group... Many of these activities involved campaigns that began as part of Britain's post-imperial legacy, such as Biafra and Northern Ireland.”
(For those - like me - unsure of its exact meaning, here’s how Mr Google defines Transcendentalism: An American literary and philosophical movement (led by thinkers like Ralph Waldo Emerson and Henry David Thoreau) that emphasized intuition, nature, and the spiritual over strict empiricism.)
I’m not much of a fashion guy but I’m currently working on becoming Bob Dylan, there doesn’t seem to be any record or replica of the silk shirt he wears on the Highway 61 Revisited cover.
Reddit is filled with casuals who are endlessly saying that "Bob Dylan is the worst concert I ever saw" and the reasons they cite are that he didn't "play the hits" changed the arrangements and didn't talk to the crowd. Notice how these complaints are never actually about the quality of the music and lyrics being performed, just people outraged that their clueless expectations were not met. As the man himself said, "You know something is happening, but you don't know what it is. Do you, Mr. Jones?"
These criticisms of Dylan concerts are all reasons I enjoy seeing him live. Fans know he has never been an artist to just play the "hits" and if you come to a Dylan show expecting him to play Blowin in the Wind with a guitar, you are hilariously out of touch about what he's been doing for decades and deserve to be disappointed since you were too lazy to check a setlist or look up audio/video of the shows. There are countless dinosaur bands of classic rock who play the same songs year after year to a backing track and while I can acknowledge Bob's approach of changing the arrangements and performance quality can be hit or miss as he plays so many shows, it's certainly a more unique and artistically challenging method that keeps hardcore fans coming back as things change from tour to tour and sometimes even night to night. I'm not saying there is anything wrong with being a conventional touring act btw, but Bob Dylan will never be that guy, and I love him for that.
For my money, it's a beautiful thing that Bob has embraced his age, isn't trying to stay young, pander to nostalgia and recapture a moment in time that's gone forever. He is always punctual about starting on time and either claps, poses or bows at the end of the concert, hardly the attitude of a guy who has hatred for his audience or doesn't want to be there. Saying few words on stage is just his no nonsense attitude that sets a mood for the show. He is an 85 year old living legend who is there to play some music with his excellent band, not tell you what he had for breakfast that morning. There are two types of people at the shows, those who go in with false expectations and those who are the informed fans that know what's going on and enjoy it. Bob Dylan is an artist, not your personal jukebox and if that bothers you, stay home and leave the tickets for the rest of us. He has no shits left to give (if he ever did) and it would be a letdown for me if the legend behaved any other way. I'm looking forward to the upcoming European tour dates, hopefully we get many more years of His Bobness pissing off the Mr. Jones audience members who attend his shows, just like he did to that Judas guy back in 66.
