The 80 best Bob Dylan songs – with not a greatest hit in sight
You’ve probably heard Like A Rolling Stone, so to celebrate the poet laureate of rock ‘n’ roll’s 80th birthday we bring you the 80 greatest essential Bob Dylan songs that don’t typically appear on ‘greatest hits’ or ‘essential’ collections
We celebrate Bob Dylan’s 80th birthday
Image: Pictorial Press Ltd / Alamy Stock Photo
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 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, 1964 Ghosting existed in the ’60s too.
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.
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’sLucky 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-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, 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 onSeptember 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.”
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…)
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.
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.
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.
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.
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.
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.
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