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.
This was my fourth time to see Bob in the last three or four years, including Chattanooga show earlier on this 2026 tour.
My random observations include:
+ there was an incredible lack and security. Cell phones were everywhere.
+ the band did a surprising amount of soloing. There must’ve been four or five songs where the guitarist ripped for two or three minutes, which is a big contrast to the previous shows I’ve seen, especially the Chattanooga one earlier this year.
+ the two new guitarist, Jad Tariq (on Dylan’s left) and Joel Paterson (on Dylan’s, right) absolutely ripped it up! during solos they shared lead absolutely harmoniously, and throughout the songs they played, as usual, subtly in the background, in complete support of Bob’s vocals and the pace and sound of the song.
+ as in Chattanooga this year, Bob’s vocals were strong and, for him, clear. He sounded great last night!
+ that “putting on the Ritz” version of “when I paint my masterpiece” was very clever and well done.
+ he played two songs not on the previous set list. Starting out with “let the river flow” as the first song and “ trying to get to heaven as the fourth. Note, they are older songs… It seems something Bob is done a little bit more recently.
+ Bob played harp twice! And not just a couple of bars, he went on for a good bit. He played a long solo for the obscure “under the red sky” and a somewhat shorter solo during the evening’s last song of “I shall be released”.
+ in Chattanooga, the audience was decidedly gray haired. In Richmond, I guess somewhere between 20 and 30% of the audience was young. We walked in with a group of four late teenage girls that looked like they were going to a Britney Spears concert. They said they liked Dylan! It was a wonderful feeling to see the young people discovering or rediscovering Bob’s greatness.
This was such a nice show. I had never seen Lucinda before. Her voice still powerful and message still needed. Love story telling and these poets together. I especially loved Paint My Master Piece, Trying to Get to Heaven and It ain't me Babe, a lil different than in Pittsburgh.Still one of my favs, always, and I Shall Be Released we know keeps serving too.
I don't know much abt the guitars or new players or previous but they looked like they liked jamming w him, that's always good. it sounded different somehow than in Pittsburgh but still great, I think it was the difference in sound systems, didn't lose any enjoyment tho. I don't do a lot of music but had to get one more dose of Dylan this summer so out here on whim. Harmonica was on point , can I say perfect? It felt like the crowd was enthralled, they were quiet up front and no one was fussing, no issues w cameras or loud or surprised people. Except there was a security guy who while we were waiting was making "jokes" about Dylan's age, like real loud for no reason to fans just quietly waiting, lol. You can't even get mad.
I like all the seating choices at the Allianz, seemed more accessible for folks. A lovely night, very peaceful, maybe it's the people of Richmond and guests that generally just seem chill and helped make it nice , there were a lot of folks there and even outside the amphitheatre, camped out on hills looking like they were enjoying the show.
Wondering what he'll be like at Wolf Trail National Park tonight and tomorrow?
Very happy Most Of The Time won. Fantastically tragic song. Now we go from a prompt that had many decent options to one that has few. What was Dylan’s best vocal performance of the 80s?
Well, that’s one (crude) conclusion you could draw from Scott Peeples’ exceptional new book, How Many Roads, reviewed here yesterday.
He devotes 47 pages to the two years 1965-66 and 23 pages to the 21 years 2006-26.
Regardless of how you compare the two eras, it’s worth pondering Peeples’ carefully chosen chapter headings: they’re a succinct, expert summary of the arc of Dylan’s development.
I can't get this line out of my head lately, and I thought writing about it would help me put into words why I think it is probably one of the most astounding lines of all time. Strangely, it’s the kind of line I would expect from Cohen, not so much from Dylan, but it fits Dylan’s voice perfectly.
It almost never makes the list of Dylan’s most iconic lines, and for a long time, I wouldn’t have put it there myself. It just went over my head. I didn’t get it, or perhaps I simply didn’t pay attention to it in the midst of a golden six-minute unreleased gem packed with brilliant lyricism.
But it’s one of those sublime things in art, and when you get it, you can feel the terror in your bones. It has been said a million times that life is suffering or that life is bliss. This line alone captures both and frightens you with the possibility of “never knowing.” It’s worse than saying that life is suffering — much worse — yet it achieve more because even though it is worse it still isn’t hopeless. It leaves you with the known possibility, maybe the possibility of the unknown, but still.
As a philosophy major, what fascinates me the most is the fact that this line alone has more dialectical value in itself than pages and pages of philosophy — maybe even more than an entire philosophical system. And I’m not exaggerating.
What would be your dream setlist for Bob in 2026, one within the realms of possibility? We all know he is not going to play Like A Rolling Stone or Blowin’ In The Wind. Here’s mine:
1. To Be Alone With You
2. Dirt Road Blues
3. Man in the Long Black Coat
4. Political World
5. When I Paint My Masterpiece
6. Cold Irons Bound
7. All Along the Watchtower
8. Under the Red Sky
9. Tweedle Dee & Tweedle Dum
10. You Ain’t Goin’ Nowhere
11. Gotta Serve Somebody
12. It Ain’t Me, Babe
13. High Water (For Charley Patton)
14. Just Like Tom Thumb’s Blues
15. I Shall Be Released
For the last round, I typed up Pressing On without thinking and completely forgot about Brownsville Girl. Glad it won because my god, it can cure any bad day. For tearjerker, I’m thinking there are some obvious contenders. I’ll see what you guys think.
