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

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

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

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

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

76. My Own Version of YouRough and Rowdy Ways, 2020Realising thislist 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, 1964Ghosting existed in the ’60s too. 

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

73. Tonight I’ll Be Staying Here With YouNashville Skyline, 1969Reinvented 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, 1970About 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.

69. Huck’s Tune Tell Tale Signs: The Bootleg Series Vol. 8, 2007Things 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’sLucky You from 2007. 

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

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

66. If You See Her, Say HelloBlood 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-everChristmas 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, 1969Written for Johnny Cash, this record has a whole session of drunk-sounding duets.

63. I and I Infidels, 1983These 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 onSeptember 11 2001.

61. Stuck Inside of Mobile with the Memphis Blues AgainBlonde on Blonde, 1966Anyone 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, 1966The 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, 2001Dylan is a fan of puns and dad jokes

57. Farewell Angelina The Cutting Edge, Bootleg Series Vol. 12, 1965Have 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 MoodFallen Angels, 2016A 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, 1961He was.

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

53. Santa-Fe The Bootleg Series Volumes 1-3, 1967Echoing 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, 1997ishGoing 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, 2020Dylan’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, 1997A 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, 1973Dylan, 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 RainBlood 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, 1985The video was directed by Eurythmics frontman Dave Stewart.

46. Cold Irons Bound Masked And Anonymous, 2003The 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, 2006Weary warrior at the world’s end.

44. Mr Bojangles Dylan, 1973Long 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, 1976Actual 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, 1964One of the other sides of Bob Dylan was agony uncle.

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

40. One Too Many MorningsThe Times They Are A-Changin’, 1964Listen 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 InThe Times They Are A-Changin’, 1964Apparently 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, 2003The forgotten Civil War film Gods and Generals gave us this gem on its soundtrack.

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

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

35. Forever Young Side Tracks, 1973A ‘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, 1985ishLook for the track with ‘Rehearsal with pedal steel’ to find Dylan in laid-back holiday mode.

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

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

31. Up to Me – Take 2 Side Tracks, 1975ishSo 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 LeatherThe Times They Are A-Changin’, 1964Tender conversation between sweethearts from the days travelling to Spain was more straightforward.

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

28. Tomorrow Is a Long TimeSide 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 MeNew Morning, 1970Yes, Bob Dylan can be upbeat! Memorably used in the opening credits of The Big Lebowski.

26. Angelina The Bootleg Series Volumes 1-3, 1981So 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, 1989Melodic malaise.

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

23. Bob Dylan’s DreamThe Freewheelin’ Bob Dylan, 1963Steeped 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, 1964His most intimate, self-reflective love/lust song.

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

20. Lay Down Your Weary Tune Side Tracks, 1963Giving 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 LowlandsBlonde On Blonde, 1966That thin, wild mercury sound in devotion to then wife Sara Lowndes.

17. SaraDesire, 1976A 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, 1989A 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 RowHighway 61 Revisited, 1965Dystopian fairy tale crowns the best album of the ’60s.

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

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

11. Idiot WindBlood On The Tracks, 1975Sonic venom.

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, 1997Outtake 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, 2020Gloriously meandering masterpiece from his latest album.

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

06. Blind Willie McTell The Bootleg Series Volumes 1-3, 1983This 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, 1975Obviously 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, 2006Dylan’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, 1997ishNot 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.

01. Brownsville Girl Knocked Out Loaded, 1986The 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