The 80 best Bob Dylan songs – with not a greatest hit in sight

Bob Dylan turns 80 this month. To celebrate, this is a countdown of his best – but slightly more obscure – songs to revisit. Some may be familiar to you, some you may never have come across before. There is always something new to hear in every listen.

All the songs are gathered together in our Spotify playlist, and links to official versions on YouTube have been added where they exist.

Your 7 hours 17 minutes of Dylan delights begins now!

80.  Tweeter and the Monkey Man
The Traveling Wilburys Vol 1, 1988
Start off with a surprising Springsteen pastiche from the ultimate grumpy uncle supergroup.

79. Fourth Time Around
Blonde on Blonde, 1966
Ponder the Beatles/Dylan synergy during this riff on their Norwegian Wood.

78. The Ballad of Frankie Lee and Judas Priest
John Wesley Harding, 1967
Contains the most revealing Dylan lyric: “Nothing is revealed.”

77. Masters of War
The Freewheelin’ Bob Dylan, 1963
Protest singer at his most serious and unforgiving.

76. My Own Version of You
Rough and Rowdy Ways, 2020
Realising this list in some way reflects my own version of me… I’d encourage you to find out what your selection would say about your own version of you!

75. I Don’t Believe You (She Acts Like We Never Have Met)
Another Side of Bob Dylan, 1964
Ghosting existed in the ’60s too. 

74. Queen Jane Approximately
Highway 61 Revisited, 1965
Still not over being ghosted. 

73. Tonight I’ll Be Staying Here With You
Nashville Skyline, 1969
Reinvented as a country crooner, Dylan explained to Rolling Stone at the time: “I tell you, you stop smoking those cigarettes and you’ll be able to sing like Caruso.”

72. I Feel a Change Comin’ On
Together Through Life, 2009
More optimistic about change than he was when times were first a-changin’.

71. Day of the Locusts
New Morning, 1970
About picking up an honorary degree at Princeton. Still waiting on a composition about the other one he received at St Andrews in 2004.

70. New Morning
Another Self Portrait, The Bootleg Series Vol. 10, 1970
Thirteen Dylan songs include the word happy, but this is the happiest, with added horns on this record. Since the early 1990s there have been a steady stream of official ‘bootleg’ releases containing alternate versions of famous songs, cut album tracks or live performances. Many of the following selections on this list come from these collections.

Dylan At The Bitter End

His life is a-changin' Performing at the Bitter End club in NYC's Greenwich Village in 1961. Image: Sigmund Goode/Michael Ochs Archive/Getty Images

69. Huck’s Tune
Tell Tale Signs: The Bootleg Series Vol. 8, 2007
Things Have Changed won Dylan an Oscar for his song from the film Wonder Boys (watch the great video for it if you haven’t already) and this was for another director Curtis Hanson’s Lucky You from 2007. 

68. Eternal Circle
The Bootleg Series Volumes 1-3, 1963
Take me on a trip back to a smoky Greenwich Village club.

67. Soon After Midnight
Tempest, 2012
I’m searching for phrases, to sing its praises.

66. If You See Her, Say Hello
Blood on the Tracks, 1975
“She might think that I’ve forgotten her, Don’t tell her it isn’t so.”

65. Must Be Santa
Christmas in the Heart, 2009
Festive frolics on the best-ever Christmas album! This video comes from Dylan’s wig phase:

But classic songs aren’t just for Christmas, and Christmas in the Heart was the first of several albums Dylan recorded through the last decade revisiting ‘the great American songbook’. More on that soon.

64. Wanted Man
Travelin’ Thru, The Bootleg Series Vol.15, 1969
Written for Johnny Cash, this record has a whole session of drunk-sounding duets.

63. I and I
Infidels, 1983
These stories are probably never true but are nevertheless entertaining. Supposedly Leonard Cohen told Dylan that Hallelujah took two years to write. Cohen was impressed by I and I. “Took 20 minutes,” said Dylan. A live version Dylan did of Hallelujah is also amazing if you can find it.

62. High Water (For Charley Patton)
Love and Theft, 2001
“It’s bad out there, high water everywhere,” Dylan sang on a record released on  September 11 2001.

61. Stuck Inside of Mobile with the Memphis Blues Again
Blonde on Blonde, 1966
Anyone reading this list forensically will want to point out that in fact this song appears on the Greatest Hits 2 collection from 1971. This may not be your only complaint about the list. The songs here are based around songs that aren’t included in the ‘best of’ CDs people would most likely come across. As Dylan says in this one: “I hope you’re satisfied.”

60. Tell Me, Momma
Live at the ‘Albert Hall’, The Bootleg Series Vol 4, 1966
The opening volley from the electric set of the ‘Judas’ concert.

59. One More Cup of Coffee
Desire, 1975
Stirring.

58. Po’ Boy
Love and Theft, 2001
Dylan is a fan of puns and dad jokes

57. Farewell Angelina
The Cutting Edge, Bootleg Series Vol. 12, 1965
Have a think about how many words rhyming with Angelina you can think of – ones you might be able to connect together in a narrative – then see the next mention of the name in this list at 26…

56. Melancholy Mood
Fallen Angels, 2016
A taste of the five CDs of great American songbook songs.

55. I Was Young When I Left Home
No Direction Home, The Bootleg Series Vol 7, 1961
He was.

54. Long and Wasted Years
Tempest, 2012
A frequent finisher of his live sets in recent times.

53. Santa-Fe
The Bootleg Series Volumes 1-3, 1967
Echoing the casual brilliance of The Basement Tapes, so for more check out the surfeit of releases.

52. Red River Shore
Tell Tale Signs: The Bootleg Series Vol. 8, 1997ish
Going by the number of entries from this bootleg collection, Tell Tale Signs may be Dylan’s greatest record – or two of his best, Oh Mercy and Time Out Of Mind, could have been even better.

51. Murder Most Foul
Rough and Rowdy Ways, 2020
Dylan’s longest song – almost 17 minutes – materialised out of nowhere in the midst of the first wave of the pandemic and invents its own genre, a free-consciousness rumination of the last 60 years of American history.

50. Love Sick
Time Out Of Mind, 1997
A highlight of recent live shows with savage lyric changes: “You thrilled me to my heart, and you ripped it all apart.”

49. Billy 4
Pat Garrett & Billy The Kid, 1973
Dylan, an almost mythical figure himself, rewrote an American myth when scoring Sam Peckinpah’s western, where he also pops up as a character called Alias. 

48. Buckets of Rain
Blood On The Tracks, 1975
“Life is sad, life is a bust, all you can do is do what you must.”

47. Emotionally Yours
Empire Burlesque, 1985
The video was directed by Eurythmics frontman Dave Stewart.

46. Cold Irons Bound
Masked And Anonymous, 2003
The bemusing film Dylan wrote and starred in, Masked and Anonymous, delivered some storming live performances, including this version of the Time Out Of Mind track.

45. Ain’t Talkin’
Modern Times, 2006
Weary warrior at the world’s end.

44. Mr Bojangles
Dylan, 1973
Long a fan of a good cover version, this appears on a surreptitiously released collection of warm-up studio songs, also including Big Yellow Taxi, The Boxer and Can’t Help Falling in Love.

43. Seven Days
The Bootleg Series Volumes 1-3, 1976
Actual Rolling Stone Ronnie Wood performed the song at the concert to celebrate Dylan’s 30th anniversary in 1992.

42. To Ramona
Another Side Of Bob Dylan, 1964
One of the other sides of Bob Dylan was agony uncle.

41. Visions of Johanna
Blonde On Blonde, 1966
“The ghost of electricity howls in the bones of her face.”

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40. One Too Many Mornings
The Times They Are A-Changin’, 1964
Listen to this then listen to the live recording from the ‘Judas’ concert from 1966 then Hard Rain a decade later to find three songs by three different Dylans.

39. When the Ship Comes In
The Times They Are A-Changin’, 1964
Apparently inspired by a hotel clerk refusing Dylan a room for looking unwashed.

38. ‘Cross the Green Mountain
Tell Tale Signs: The Bootleg Series Vol. 8, 2003
The forgotten Civil War film Gods and Generals gave us this gem on its soundtrack.

37. Abandoned Love
Side Tracks, 1975
A jolly break-up song for a change.

36. Sugar Baby
Love And Theft, 2001
Not just a break-up song but a totally broken, never-picking-up-the-pieces-again one.

35. Forever Young
Side Tracks, 1973
A ‘greatest hit’ but this demo is better than either studio version. Sentimental but not sappy, simple as a nursery rhyme. For the other end of the spectrum check out Meat Loaf’s version.

34. Caribbean Wind
Trouble No More: The Bootleg Series, Vol. 13, 1985ish
Look for the track with ‘Rehearsal with pedal steel’ to find Dylan in laid-back holiday mode.

33. Ballad of a Thin Man
Highway 61 Revisited, 1965
A song dedicated to anyone not liking this list.

32. Series of Dreams
The Bootleg Series Volumes 1-3, 1989
Music with momentum pushed along by producer Daniel Lanois.

31. Up to Me – Take 2
Side Tracks, 1975ish
So where would greatest hits like Like a Rolling Stone and Blowin’ in the Wind land in this list? That’s up to you, like this is Up to Me.

30. Boots of Spanish Leather
The Times They Are A-Changin’, 1964
Tender conversation between sweethearts from the days travelling to Spain was more straightforward.

29. Standing in the Doorway
Time Out Of Mind, 1997
Haunting. Pretty hopeless. One for those suffering like a fool…

28. Tomorrow Is a Long Time
Side Tracks, 1963
“The one recording I treasure most,” said Dylan about Elvis’ cover of this song. (Another that has appeared on Greatest Hits 2, but still…)

27. The Man in Me
New Morning, 1970
Yes, Bob Dylan can be upbeat! Memorably used in the opening credits of The Big Lebowski.

26. Angelina
The Bootleg Series Volumes 1-3, 1981
So how do your rhyming skills compare to a Nobel Prize for Literature winner?  Dylan weaves a song around the following words that rhyme with Angelina: concertina, hyena, subpoena, Argentina, arena.

25. Most of the Time
Oh Mercy, 1989
Melodic malaise.

24. Black Diamond Bay
Desire, 1976
Energetic pulp fiction narrative set against an earthquake.

Dylan at 80 1462

Rock and Rolling Thunder Onstage in 1975. The tour was the subject of a 2019 Martin Scorsese documentary. Image: Ron Harvey/Netflix/Everett Collection; courtesy of Alamys

23. Bob Dylan’s Dream
The Freewheelin’ Bob Dylan, 1963
Steeped in nostalgia, loss and regret, Dylan has rarely sounded more wizened. He was 21 at the time of recording. He’s been younger than that since.

22. Mama, You Been On My Mind
The Bootleg Series Volumes 1-3, 1964
His most intimate, self-reflective love/lust song.

21. Chimes of Freedom
Another Side Of Bob Dylan, 1964
A call about not sheltering from the storm but striking against it with righteousness.

20. Lay Down Your Weary Tune
Side Tracks, 1963
Giving a new spin to an old Scottish ballad keeps the traditional timeless.

19. Tight Connection to My Heart, performed by Sheila Atim
An overlooked track from unloved album Empire Burlesque (but with a cracking video directed by Taxi Driver and Raging Bull writer Paul Schrader) turned out to be a true diamond in the rough after it was resurrected and reinvented for the West End smash Girl From The North Country based around, like this list, lesser-known Dylan songs. Sheila Atim won an Olivier Award for her spellbinding performance.

18. Sad-Eyed Lady of the Lowlands
Blonde On Blonde, 1966
That thin, wild mercury sound in devotion to then wife Sara Lowndes.

17. Sara
Desire, 1976
A different stage in their relationship, reminding her of the time he was “staying up for days in the Chelsea Hotel, writing Sad-Eyed Lady of the Lowlands for you”.

16. Shooting Star
Oh Mercy, 1989
A hymn to regret and what might have been.

15. Born In Time
Tell Tale Signs: The Bootleg Series Vol. 8, 1989ish
“Just when I thought you were gone, you came back” – this song signals a return to form after a rum decade – so of course it was left off Oh Mercy.

14. Desolation Row
Highway 61 Revisited, 1965
Dystopian fairy tale crowns the best album of the ’60s.

13. You’re a Big Girl Now
Side Tracks, 1974
Blood on the Tracks outtake captures the sound of a heart being wrenched.

12. Precious Angel
Slow Train Coming, 1979
For someone often so cynical and contrary, this comes from the time Dylan was reborn with disconcerting sincerity.

11. Idiot Wind
Blood On The Tracks, 1975
Sonic venom.

BOB DYLAN and JOAN BAEZ at Savoy Hotel gardens London in May 1965

Visions of Joan. Joan Baez joins Dylan in London's Embankment Gardens in 1965. Image: Pictorial Press Ltd / Alamy Stock Photo

10. Diamonds and Rust, Joan Baez
So this is not a Dylan song but nobody has cracked the Dylan enigma like old flame Baez. Including it in this list is a bit of a cheat but as well as being one of the all-time great love and loss songs, it reveals more about “the unwashed phenomenon, the original vagabond” than these 79 other tracks combined so an incredibly important ‘Dylan song’.

09. Dreamin’ of You
Tell Tale Signs: The Bootleg Series Vol. 8, 1997
Outtake from the Time Out Of Mind sessions combining fragments from different songs with an urgent and energetic beat. The music video stars the late, great Harry Dean Stanton.

08. Key West (Philosopher Pirate)
Rough and Rowdy Ways, 2020
Gloriously meandering masterpiece from his latest album.

07. It’s Alright, Ma (I’m Only Bleeding)
Bringing It All Back Home, 1965
Endlessly quotable tirade against malignant forces and pathetic people more proliferate today than ever.

06. Blind Willie McTell
The Bootleg Series Volumes 1-3, 1983
This 1983 offcut is hidden treasure that was found long ago. It’s the only one on this list that appears in the ‘essential’ collection. Strictly it shouldn’t be on this list but it’s here as testament to the fact some of the best songs ever written might never have been heard.

05. Mr Tambourine Man – Live at Boston Music Hall
The Bootleg Series, Vol 5, 1975
Obviously one of Dylan’s most famous songs, but this recording from the infamous Rolling Thunder Revue tour writes it anew. Intimate, feverishly impassioned; transformative and transcendent. The performance features in Martin Scorsese’s documentary/mockumentary from 2019.

04. Where Are You Tonight? (Journey Through Dark Heat)
Street-Legal, 1978
“If you don’t believe there’s a price for this sweet paradise, just remind me to show you the scars.”

03. Workingman’s Blues #2
Modern Times, 2006
Dylan’s best song of the 21st century matches any of his canonical classics, a paean to the proletariat (and how many songs use that word in their opening verse?), a voice weary but resolute that you hear your own story echoing in, especially if you’ve had one of those days.

02. Can’t Wait -Alternate Version #2
Tell Tale Signs: The Bootleg Series Vol. 8, 1997ish
Not the Time Out Of Mind version, not even the first alternate take on this record. Only available in a deluxe boxset, this song is extra valued for its difficulty to discover (before it just appeared on Spotify one day). A simmering dirge about obsession to become obsessed by.

Bob Dylan Hyde Park - London

Ballad of a grin man At his last UK performance, in London's Hyde Park in 2019 Image: Brian Rasic/WireImage

01. Brownsville Girl
Knocked Out Loaded, 1986
The Ulysses of music, an 11-minute ramble (co-written with playwright Sam Shepard) about nothing and everything, epic and ridiculous. And in another reminder that Dylan’s best songs are the least listened to, there’s an even better unofficial bootleg version out there…

UPDATE: To celebrate Bob’s 81st birthday on 24/5/2022, another song has been added to the playlist. Since this article was written, a new bootleg collection, Springtime in New York was released, including the aforementioned alternate take of Brownsville Girl. So New Danville Girl is an apt 81st entry.

Listen to this playlist at spoti.fi/3bi4vBG and send praise or complaints to @stevenmackenzie

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