It happens to everyone at some point; you hear a Dylan song (or another band’s cover of a Dylan song) and your interest is piqued. You want to explore more of his music, but you don’t know where to start. He has dozens of albums and hundreds of songs, so it’s a little overwhelming.
I started my Dylan obsession with Blonde On Blonde and then moved on to his Greatest Hits, Volumes 1, 2 & 3. From there I moved to other albums I found in used CD stores, progressing with no respect to context or chronology. Chronology is important for Dylan’s albums. His sound has changed more frequently than the plot of a daytime soap and it can be hard to follow.
Another thing to remember is that Dylan’s songs, like most songs from the pre-internet days, were not meant to be cherry-picked. If you don’t listen to the album tracks in order, you’re not getting the full experience. That being said, I can’t deny that it’s cheaper and easier to just buy the songs that have stood the test of time.
Top Ten Bob Dylan Albums
If you want to start your odyssey with Dylan’s best work, buy these albums one by one. They’re not in chronological order, but they’ll help you figure out which ‘sound’ you like the best.
- Blood On The Tracks
- Blonde On Blonde
- Highway 61 Revisited
- The Times They Are A-Changin’
- Bringing It All Back Home
- Street-Legal
- Another Side Of Bob Dylan
- Desire
- Planet Waves
- Oh Mercy
I don’t expect everyone to agree with this ranking. Everyone has their favorite albums, but you can’t go wrong buying these first. I should add that I intentionally left live albums and bootlegs off the list. This post is meant for music fans who are new to Dylan. If you’re one of them, I think you’re better served by listening to the songs (and the versions of songs) that Dylan himself intended to be heard by his audience. If you like what you hear on the polished albums, go out and buy the less-refined bootlegs. Start with these:
- The Bootleg Series, Vols. 1-3: Rare And Unreleased, 1961-1991
- Tell Tale Signs: the Bootleg Series Vol. 8
- The Basement Tapes
Dylan left more original masterpieces off his albums than most great musicians even collaborate on in their lifetimes.
Bob Dylan Discography & Cheat Sheet
Some Dylan albums need to purchased whole because there are so many good songs that you’d pay more for them individually than as a set. Still, no one should have to buy the bad not so good albums just to get one or two tracks. Here are my suggestions on what albums or songs to buy to fill out your budding Dylan collection.
Bob Dylan (1962) – This album is worth buying in full if you like traditional folk music. Only two songs are Dylan originals (Song to Woody & Talkin’ New York). If you want to sample some tracks before buying the whole thing, buy these songs:
- You’re No Good
- Talkin’ New York
- In My Time Of Dyin’
- Man Of Constant Sorrow
- Fixin’ To Die
- Pretty Peggy-O
- Highway 51
- Gospel Plow
- Baby, Let Me Follow You Down
- House Of The Risin’ Sun
- Freight Train Blues
- Song To Woody
- See That My Grave Is Kept Clean
The Freewheelin’ Bob Dylan (1963) – Buy this entire album. This is when Dylan started to let his creativity flow and jumped to the top of the folk scene. I still believe Don’t Think Twice, It’s All Right is the sweetest goodbye song ever written.
- Blowin’ In The Wind
- Girl From The North Country
- Masters Of War
- Down The Highway
- Bob Dylan’s Blues
- A Hard Rain’s A-Gonna Fall
- Don’t Think Twice, It’s All Right
- Bob Dylan’s Dream
- Oxford Town
- Talking World War III Blues
- Corrina, Corrina
- Honey, Just Allow Me One More Chance
- I Shall Be Free
The Times They Are A-Changin’ (1964) – Buy this entire album. This is when everyone noticed Dylan’s ability to take a complex subject and distill it into its simplest form. After Medgar Evers’ racially-motivated murder, only Bob Dylan could have written a powerful song (Only A Pawn In Their Game) lamenting the marginalization and exploitation of poor white men in the South.
- The Times They Are A-Changin’
- Ballad Of Hollis Brown
- With God On Our Side
- One Too Many Mornings
- North Country Blues
- Only A Pawn In Their Game
- Boots Of Spanish Leather
- When The Ship Comes In
- The Lonesome Death Of Hattie Carroll
- Restless Farewell
Another Side Of Bob Dylan (1964) – Buy this entire album. I’ve always loved the alliteration that opens Spanish Harlem Incident, and It Ain’t Me Babe and My Back Pages telegraphed Dylan’s growing disillusionment with the vain and ineffectual folk movement.
- All I Really Want To Do
- Black Crow Blues
- Spanish Harlem Incident
- Chimes Of Freedom
- I Shall Be Free #10
- To Ramona
- Motorpsycho Nightmare
- My Back Pages
- I Don’t Believe You
- Ballad In Plain D
- It Ain’t Me Babe
Bringing It All Back Home (1965) – Buy this entire album. Half the tracks are acoustic and the rest are electric. This represents the moment when Dylan renounced his unwanted role as “the voice of a generation.” Maggie’s Farm and It’s All Over Now, Baby Blue were direct messages to his overly-demanding fans and critics alike.
- Subterranean Homesick Blues
- She Belongs To Me
- Maggie’s Farm
- Love Minus Zero/No Limit
- Outlaw Blues
- On The Road Again
- Bob Dylan’s 115th Dream
- Mr. Tamborine Man
- Gates Of Eden
- It’s Alright Ma (I’m Only Bleeding)
- It’s All Over Now, Baby Blue
Highway 61 Revisited (1965) – Buy this entire album. Smarter people than me have analyzed the groundbreaking nature of this album over and over again. You can ask Mr. Google what it all means. I’ll only say that Like A Rolling Stone is arguably the greatest song ever created, and Tombstone Blues has what might be the weirdest line ever sung: “The sun’s not yellow, it’s chicken.”
- Like A Rolling Stone
- Tombstone Blues
- It Takes A Lot To Laugh, It Takes A Train To Cry
- From A Buick 6
- Ballad Of A Thin Man
- Queen Jane Approximately
- Highway 61 Revisited
- Just Like Tom Thumb’s Blues
- Desolation Row
Blonde On Blonde (1966) – Buy this entire album. There’s not a single bad song on it. And don’t make the common mistake of thinking that Rainy Day Women is about getting high. It’s about persecution.
- Rainy Day Women #12 & 35
- Pledging My Time
- Visions Of Johanna
- One Of Us Must Know (Sooner Or Later)
- I Want You
- Stuck Inside of Mobile With The Memphis Blues Again
- Leopard-Skin Pill-Box Hat
- Just Like A Woman
- Most Likely You Go Your Way And I’ll Go Mine
- Temporary Like Achilles
- Absolutely Sweet Marie
- 4th Time Around
- Obviously 5 Believers
- Sad Eyed Lady Of The Lowlands
John Wesley Harding (1968) – Buy this entire album. Dylan returned to his story-telling roots for this one and introduced a smoother singing voice that would foreshadow his move to a country and western sound that would endure until New Morning in 1970.
- John Wesley Harding
- As I Went Out One Morning
- I Dreamed I Saw St. Augustine
- All Along The Watchtower
- The Ballad Of Frankie Lee And Judas Priest
- Drifter’s Escape
- Dear Landlord
- I Am A Lonesome Hobo
- I Pity The Poor Immigrant
- The Wicked Messenger
- Down Along The Cove
- I’ll Be Your Baby Tonight
Nashville Skyline (1969) – Some people love this album. I think it’s okay. Dylan was becoming reclusive and angry because of his lack of privacy, fans’ unrealistic expectations, and the constant preening of his critics. He was trying to do something a little different and unpredictable, so he doubled down on his classic country sound. I think you can get away with just buying the following tracks.
- Girl From The North Country (Duet with Johnny Cash)
- Nashville Skyline Rag
- To Be Alone With You
- I Threw It All Away
- Peggy Day
- Lay Lady Lay
- One More Night
- Tell Me That It Isn’t True
- Country Pie
- Tonight I’ll Be Staying Here With You
Self Portrait (1970) – Bob Dylan supposedly put this less-than-stellar album out on purpose. He explained that everyone except him was cashing in on bootleg copies of his outtakes and live renditions of original and cover songs. So he put these songs together as a way to give the people what they wanted. Some people love this album, but I’m not one of them. These songs are worth buying:
- All The Tired Horses
- Alberta #4
- I Forgot More Than You’ll Ever Know
- Days Of 49
- Early Mornin’ Rain
- In Search Of Little Sadie
- Let It Be Me
- Little Sadie
- Woogie Boogie
- Belle Isle
- Living The Blues
- Like A Rolling Stone
- Copper Kettle (The Pale Moonlight)
- Gotta Travel On
- Blue Moon
- The Boxer
- Mighty Quinn, The (Quinn The Eskimo)
- Take Me As I Am (Or Let Me Go)
- Take A Message To Mary
- It Hurts Me Too
- Minstrel Boy
- She Belongs To Me
- Wigwam
- Alberta #2
New Morning (1970) – This album is pretty good. Dylan finally returned to his famous voice, and he began experimenting with jazz and blues sounds for a friend’s play. He eventually backed out of the play and just threw the songs on this album, which is why it seems like a mish-mash of varying sounds.
- If Not For You
- Day Of The Locusts
- Time Passes Slowly
- Went To See The Gypsy
- Winterlude
- If Dogs Run Free
- New Morning
- Sign On The Window
- One More Weekend
- The Man In Me
- Three Angels
- Father Of Night
Pat Garrett & Billy The Kid (1973) – It’s a soundtrack, so several tracks are just background music and there are four versions of the same song (Billy). You can probably get away with downloading these songs:
- Billy (Main Title Theme)
- Workin’ For The Law (Cantina Theme)
- Billy 1
- Bunkhouse Theme
- River Theme
- Turkey Chase
- Knockin’ On Heaven’s Door
- Final Theme
- Billy 4
- Billy 7
Dylan (1973) – This album was put together by Columbia Records without Dylan’s input or consent at the end of his contract. It’s basically a series of outtakes from prior recording sessions. If you’re new to Dylan, this should be one of the last records you buy. That’s not because it’s bad, but because it’s an album of covers. I like this album. Dylan’s arrangements of Lily of the West and Sarah Jane are pretty fun.
- Lily of the West
- Can’t Help Falling in Love
- Sarah Jane
- Mr. Bojangles
- The Ballad of Ira Hayes
- Mary Ann
- Big Yellow Taxi
- A Fool Such as I
- Spanish is the Loving Tongue
Planet Waves (1974) – This album hints at Dylan’s marital unrest that would dominate Blood on the Tracks. People ask me what the most upbeat (and accessible) Bob Dylan album is, and I usually refer them to this one. Amazingly, it was recorded in just three days. I think you should buy the whole thing, but you can get away with just these songs at first:
- On A Night Like This
- Going, Going, Gone
- Tough Mama
- Hazel
- Something There Is About You
- Forever Young
- Forever Young
- Dirge
- You Angel You
- Never Say Goodbye
- Wedding Song
Blood On The Tracks (1975) – I think this is the greatest album ever made. It makes me feel like a voyeur looking through Bob Dylan’s window. Idiot Wind and You’re A Big Girl Now are so nakedly emotional that I feel a little guilty tapping my foot and singing along to them with a smile. That said, I never understood why Lily, Rosemary And The Jack Of Hearts was included. It’s a fun song, but it doesn’t fit with the other material at all. One minute Dylan’s pouring out his soul about his troubled marriage and the next he’s conjuring images of a small town bank heist. The song should have been held for the next album, Desire.
- Tangled Up In Blue
- Simple Twist Of Fate
- You’re A Big Girl Now
- Idiot Wind
- You’re Gonna Make Me Lonesome When You Go
- Meet Me In The Morning
- Lily, Rosemary And The Jack Of Hearts
- If You See Her, Say Hello
- Shelter From The Storm
- Buckets Of Rain
Desire (1976) – Through late 1975 and early 1976, Dylan toured and collaborated with a group of famous musicians known as the Rolling Thunder Revue. Their collective influence is obvious on this eccentric album. It’s more of an acquired taste than some of Dylan’s other records due to the foreign influences, but you’ll grow to love it in time. Buy the entire album, but do it after you’ve bought the other ones in the top ten list above.
- Hurricane
- Isis
- Mozambique
- One More Cup Of Coffee
- Oh, Sister
- Joey
- Romance In Durango
- Black Diamond Bay
- Sara
Street-Legal (1978) – This is easily Dylan’s most underrated album. In retrospect, we can see that it symbolizes a somewhat calm period between the boisterous Rolling Thunder Revue and Dylan’s eminent conversion to Christianity (and short-lived renunciation of his former work). I don’t understand why, but Dylan’s fans and critics gave it poor reviews. Every song except maybe New Pony is good, and New Pony isn’t that bad. For whatever reason, many people thought having back-up singers and a saxophone on the album meant Dylan sold out. Are these the same people who thought he sold out when he went electric? I’ll admit they had legitimate gripes about the sound quality of the original record, but the album been digitally remastered for CD and download. Why do people still bash these songs?
- Changing Of The Guards
- New Pony
- No Time To Think
- Baby Stop Crying
- Is Your Love In Vain?
- Senor (Tales Of Yankee Power)
- True Love Tends To Forget
- We Better Talk This Over
- Where Are You Tonight (Journey Through Dark Heat)
Slow Train Coming (1979) – Between 1978 and 1979, Dylan had a life-changing religious encounter. This is the first of four Christian-themed albums. Some people call it gospel (and a few songs are in fact gospel music), but I don’t. Most of it is rock with a religious theme. There’s a difference. If I was new to Dylan’s music, I’d buy all of his religious albums at the same time, after I had most of his other works. They’re good, but they’re different from his earlier stuff. Still, if you want to sample some songs, these are the best.
- Gotta Serve Somebody
- Precious Angel
- I Believe In You
- Slow Train
- Gonna Change My Way Of Thinking
- Do Right To Me Baby (Do Unto Others)
- When You Gonna Wake Up
- Man Gave Names To All The Animals
- When He Returns
Saved (1980) – It wasn’t clear to many fans and critics that Dylan had really become “born again,” so to speak, with Slow Train Coming. The release of Saved removed all doubt. If Dylan had joined a bizarre sect of a less mainstream religion, people would have raved about his intense, newfound spirituality. But Christianity wasn’t very fashionable with the trendsetters at the major rock rags, so they panned this impressive rock album.
- A Satisfied Mind
- Saved
- Covenant Woman
- What Can I Do For You?
- Solid Rock
- Pressing On
- In The Garden
- Saving Grace
- Are You Ready
Shot Of Love (1981) – At this point, Dylan was bending under the weight of criticism for his on-stage evangelism. This would be the last overtly Christian album he would make until his Christmas album in 2009. I think it’s a pretty good album, but you can get away with buying just a handful of tracks. Every Grain Of Sand might be the prettiest song Dylan ever created.
- Shot Of Love
- Heart Of Mine
- Property Of Jesus
- Lenny Bruce
- Watered-Down Love
- Groom’s Still Waiting At The Altar, The
- Dead Man, Dead Man
- In The Summertime
- Trouble
- Every Grain Of Sand
Infidels (1983) – Infidels has much more subtle religious allusions and undertones compared to the conspicuous overtones that dominated Slow Train, Saved and Shot of Love. It’s proven to be one of his more polarizing albums. Some fans hate it and others love it; there’s not much middle ground. I think the lyrics are some of his best, but I don’t think it’s one of his best albums by any stretch. I think the great reviews it got at the time have to be taken in context with the poor reception of his previous three records. I include this as the fourth of Dylan’s overtly religious albums, but by this time, he’s more cynical with his message than spiritual. Still, you should buy the album and decide for yourself. Like Desire, it’s an acquired taste.
- Jokerman
- Sweetheart Like You
- Neighborhood Bully
- License To Kill
- Man Of Peace
- Union Sundown
- I And I
- Don’t Fall Apart On Me Tonight
Empire Burlesque (1985) – The 80s were not good to Bob Dylan. This is probably the most dated of all of his albums. Dark Eyes is a great song and Clean Cut Kid is vintage Dylan, even if the arrangement sounds like a parody. But the rest of the songs sound like they were stolen from one of Lionel Richie’s prep sessions. I dare you to listen to I’ll Remember You and Emotionally Yours and tell me I’m wrong. There’s a version of When The Night Comes Falling From The Sky on The Bootleg Series, Vols. 1-3 that sounds like Dylan is being backed by the E Street Band. It’s really, really good. I just don’t understand how Dylan and his producers could listen to that version still choose to put this version on the final album. It has that horrible, 80s-techno, dead-fish sounding, bass drum behind it. Granted, it goes better with the other songs below, but that’s because they’re all so…80s.
- Tight Connection To My Heart
- Seeing The Real You At Last
- I’ll Remember You
- Clean Cut Kid
- Never Gonna Be The Same Again
- Trust Yourself
- Emotionally Yours
- When The Night Comes Falling From The Sky
- Something Burning, Baby
- Dark Eyes
Knocked Out Loaded (1986) – This should be one of the last albums you buy. Like Empire Burlesque, it has a very 80s sound. But what makes this one of Dylan’s worst records is that it sounds more like a series of unaffiliated singles than a cohesive album. I like Brownsville Girl because it was included on Bob Dylan’s Greatest Hits Volume 3, which wasn’t much of a hits album at all. But there are a couple of decent songs that have been overlooked.
- You Wanna Ramble
- They Killed Him
- Driftin’ Too Far from Shore
- Precious Memories
- Maybe Someday
- Brownsville Girl
- Got My Mind Made Up
- Under Your Spell
Down In The Groove (1988) – The release of Down In The Groove has to be the low point of Dylan’s career. Many critics weren’t really reviewing his work anymore, and the ones that were universally panned this album. This was supposed to be an album that coincided with the release of his latest film project, Hearts Of Fire. Dylan and Columbia went into damage control mode trying to dress it up. They eventually cut the record two more times. The final three songs listed below were added/deleted from record over time. I think this is actually an underrated album, but only because it’s rated so low. If you like Dylan’s many bootlegs and outtakes, this album has that same feel to it. Like Knocked Out Loaded, it’s a mishmash of songs recorded at disparate sessions with different backing bands. If you’re new to Dylan, check out these songs.
- Let’s Stick Together
- When Did You Leave Heaven?
- Sally Sue Brown
- Death Is Not The End
- Had a Dream About You, Baby
- Ugliest Girl In The World
- Silvio
- Ninety Miles An Hour (Down A Dead End Street)
- Shenandoah
- Rank Strangers To Me
- Got Love If You Want It
- Important Words
- The Usual
Oh Mercy (1989) – In typical fashion, Dylan followed up a string of so-so albums with another classic one. Buy this entire album. This is the point when Dylan’s age (and lifestyle) started to show in his voice. His singing took on a gruff, raspy sound that’s still present.
- Political World
- Where Teardrops Fall
- Everything Is Broken
- Ring Them Bells
- Man In The Long Black Coat
- Most Of The Time
- What Good Am I?
- Disease Of Conceit
- What Was It You Wanted
- Shooting Star
Under The Red Sky (1990) – From a critical standpoint, the 90s was Dylan’s worst decade. If I had it to do over again, I’d buy all the bootleg collections before I bought a single album (with the exception of Time Out Of Mind) from the 90s. This one doesn’t need to be part of your early collection.
- Wiggle Wiggle
- Under The Red Sky
- Unbelievable
- Born In Time
- T.V. Talkin’ Song
- 10,000 Men
- 2 X 2
- God Knows
- Handy Dandy
- Cat’s In The Well
Good As I Been To You (1992) – This is the first of two albums that were basically just recordings of Dylan playing traditional folk, blues and country songs. If you’re into older music, you’ll like this and the next album. Most of the songs are upbeat. There are lots of other Dylan records I’d buy before these two. These are purely acoustic, which Dylan hadn’t done since Another Side Of Bob Dylan, but there are no original songs on these albums.
- Frankie & Albert
- Jim Jones
- Blackjack Davey
- Canadee-i-o
- Sittin’ On Top Of The World
- Little Maggie
- Hard Times
- Step It Up And Go
- Tomorrow Night
- Arthur McBride
- You’re Gonna Quit Me
- Diamond Joe
- Froggie Went A Courtin’
World Gone Wrong (1993) – Like Good As I Been To You, this album is Dylan playing more traditional folk songs on his acoustic guitar. The only difference is that these songs are a little darker. If you like these two albums, then check out Live at the Gaslight. It’s a collection of Dylan’s live performances of mostly traditional folk songs in 1962.
- World Gone Wrong
- Love Henry
- Ragged & Dirty
- Blood In My Eyes
- Broke Down Engine
- Delia
- Stack A Lee
- Two Soldiers
- Jack-A-Roe
- Lone Pilgrim
Time Out Of Mind (1997) – After a string of not-so-good albums, most Dylan fans bought this one with their fingers crossed. It turned out to be the first in a string of new albums that have all been good. It’s a little depressing, but that just means it evokes empathy and emotion. You could do a lot worse than buy the whole album, but check out these songs first.
- Love Sick
- Dirt Road Blues
- Standing In The Doorway
- Million Miles
- Tryin’ To Get To Heaven
- Til I Fell In Love With You
- Not Dark Yet
- Cold Irons Bound
- Make You Feel My Love
- Can’t Wait
- Highlands
Love And Theft (2001) – This is a fun and upbeat album. It’s worth buying the whole thing, but you can sample these songs first:
- Tweedle Dee & Tweedle Dum
- Mississippi
- Summer Days
- Bye And Bye
- Lonesome Day Blues
- Floater (Too Much To Ask)
- High Water (for Charlie Patton)
- Moonlight
- Honest With Me
- Po’ Boy
- Cry A While
- Sugar Baby
Modern Times (2006) – Buy this whole album. Dylan continued the sound he developed on Love And Theft and it resulted in his first album to chart at #1 since Desire in 1976. If you’d like to sample some songs, these are the best:
- Thunder On The Mountain
- Spirit On The Water
- Rollin’ And Tumblin’
- When The Deal Goes Down
- Someday Baby
- Workingman’s Blues #2
- Beyond The Horizon
- Nettie Moore
- The Levee’s Gonna Break
- Ain’t Talkin’
Together Through Life (2009) – This album has a very casual and carefree vibe to it. It’s not as good as Love and Theft and Modern Times, but it’s not bad. You get the sense that the songs aren’t supposed to be taken too seriously – as in, they’re fun songs, not treatises on life. Or maybe that’s just a biased vibe I get from the prominent accordion. For a taste of album, check these songs out first:
- Beyond Here Lies Nothin’
- Life Is Hard
- My Wife’s Home Town
- If You Ever Go To Houston
- Forgetful Heart
- Jolene
- This Dream Of You
- Shake Shake Mama
- I Feel A Change Comin’ On
- It’s All Good
Christmas In The Heart (2009) – I haven’t bought this one yet, but all US royalties go to Feeding America, an organization that helps feed families during the holidays. My wife’s not too fond of Dylan and she’ll kill me if I start playing this album around the holidays.
- Here Comes Santa Claus
- Do You Hear What I Hear?
- Winter Wonderland
- Hark the Herald Angels Sing
- I’ll Be Home For Christmas
- Little Drummer Boy
- The Christmas Blues
- O Come All Ye Faithful (Adeste Fideles)
- Have Yourself A Merry Little Christmas
- Must Be Santa
- Silver Bells
- The First Noel
- Christmas Island
- The Christmas Song
- O’ Little Town of Bethlehem
Like I said earlier, this list is for people who’d like to start exploring Bob Dylan’s music and I intentionally left live albums and bootlegs off the list. It’s not supposed to be a catalog of every good song he ever sang. I compiled this for the same reason I compiled my recent list of good movies you might not have heard about. Friends are always asking for suggestions, and I thought I’d just put my thoughts in writing so I can email them the link.
Tags: Acoustic, Albums, Bob Dylan, Download, Hits, MP3, Recommendations, Rock, Top Ten










great post!