Starting with car trips and camping holidays with storytellers around fires, night sky and bugs crawling outside the tent, there are a lot of early memories of hearing my dad’s tapes and initially I was not a Dylan fan. He eventually became one of the artists I went out of my way to listen to the entire discography of, which is no small feat given there are like 60+ studio albums. Dylan is given a lot of shit for his singing voice and not being a particularly accomplished musician in terms of virtuosity but he’s a fairly chameleonic artist. His voice might not be sweet but he has many voices and sings certain lyrics with a very particular emphasis that can be heard in the list below.
Dylan has several loose genres of song, but the ones I love in particular are those that are basically just stories. Songs of escape, crime, love, jealousy, autobiography, surrealist dreams, and dialogues with the listener or a waitress. These are the types of song on offer as I see ‘em:
- Stories/Ballads/Fables
- Portraits of people (including Dylan)
- Protest songs
- More abstract poetic ramblings and/or impressionistic painting of imagery usually starring an ensemble cast of famous names
- Love songs
- What I call ‘sad bastard’ music
- Covers
I’m not as big a fan of 3. and 4. which is where a lot of his most celebrated work comes from and so I tend to discount a lot of what came out of his ‘prime’. I am a 70s-90s Dylan fan for my sins.
Narrowing down to 20 is very hard and there’s easily a hundred tracks that could be here across such a large discography but my goal is to represent:
- What grabs me so that I cannot help but listen to the rest of the song
- Songs people may never have heard of or don’t fit the typical Dylan canon
- A variety so we’re not just listening to a bunch of the same kinda stuff all day
I’ve managed to pick multiple tracks from some albums which is perhaps not fully representative but these albums are too good I’m afraid. I’ve got 3 from Desire (was nearly 4), 2 from Bringing it all Back Home, 2 from Under the Red Sky (surprised myself). I make no apologies. It’s good shit. So without further ado here it is
20 Big Ones (in playlist order)
- Under the Red Sky (Under the Red Sky)
My earliest Dylan memory. Synonymous with childhood car trips and the beginning of many stories. - Only a Hobo (Another Self Portrait aka Bootleg seris vol. 10)
Simple folk song that carries you with it in quiet tragedy. - Tweeter and the Monkey Man (Traveling Wilburys song technically but this is Dylan all over)
A Coen brothers plot bordered by driving instrumentation and violent delivery. - It’s Alright, Ma I’m Only Bleeding (Bringing it all Back Home)
Weary musing on life. One of the more famous tracks on here. Many breathless poetic refrains that dare you to keep up
’A question in your nerves is lit
Yet you know there is no answer fit
To satisfy, ensure you not to quit
To keep it in your mind and not forget
That it is not he, or she, or them, or it
That you belong to’ - Idiot Wind (Blood on the Tracks)
The song most tinged with hatred (‘I can’t even touch the books you’ve read’). A breakup song full of insults regarding the omnipresent idiot wind but also strong impressionism
‘There’s a lone soldier on the cross
Smoke pouring out of a boxcar door
You didn’t know it, you didn’t think it could be done
In the final end he won the war’
The choruses eventually include the narrator in the condemnation of human stupidity. - Isis (Desire)
A rollicking tale of adventure and regret - Mr. Tambourine Man (Bringing it all Back Home)
The longest musical request in history. A popular song but it’s also pure poetry.
’And take me disappearing through the smoke rings of my mind
Down the foggy ruins of time, far past the frozen leaves
The haunted, frightened trees, out to the windy beach
Far from the twisted reach of crazy sorrow
Yes, to dance beneath the diamond sky with one hand waving free
Silhouetted by the sea, circled by the circus sands
With all memory and fate driven deep beneath the waves
Let me forget about today until tomorrow’ - Mozambique (Desire)
Not every great song is a Nobel literature exemplar. Put this on at any party and wish you were there. Dylan is being ironic since Mozambique is not a recommended romantic destination due to the colonial war at the time. - Handy Dandy (Under the Red Sky)
Another good party tune. Who is Handy Dandy? This song will tell you with vim. The stutter on ‘Boy you’re t-talkin’ crazy’ is inspired. - Brownsville Girl (Knocked Out and Loaded)
Dylan takes 11 minutes to recount a Gregory Peck film he saw and what happened next. An almost speaking delivery, half-sung trying to cram long sentences in to tell the audience the narrator’s thoughts on the story as we go. There should probably be an intermission between this and the next track. - Highlands (Time Out of Mind)
Dylan’s longest song. 16 tired minutes and 20 verses of longing for some non-existent utopia. The highlight being Dylan roaming lost through some town and going to a diner to have an obtuse conversation with the waitress. At moments completely rambling:
’Then she says, “You don’t read women authors, do you?”
At least that’s what I think I hear her say
“Well,” I say, “how would you know? And what would it matter anyway?”
“Well,” she says, “You just don’t seem like you do”
I said, “You’re way wrong”
She says, “Which ones have you read then?” I say, “I read Erica Jong”
She goes away for a minute
And I slide up out of my chair
I step outside back to the busy street but nobody’s going anywhere’ - Country Pie (Nashville Skyline)
One of Dylan’s shortest songs makes for a good palette cleanser here. It’s fun and infectious and the guitar always gives me the sensation of marshmallow. We must imagine Dylan happy with all the ‘pie’ he’s gonna get. - Things Have Changed (Side Tracks)
Dylan’s own cynical, shuffling response to his classic ‘The Times They are a-Changin’ ’. Things are dangerous and Dylan gives every syllable the right length as can be heard in the ‘eternity’ line below:
’I hurt easy, I just don’t show it
You can hurt someone and not even know it
The next sixty seconds could be like an eternity’ - Mother of Muses (Rough and Rowdy Ways)
An invocation of the muses likely inspired by Homer but applied to figures throughout history (a recurring Dylan technique to invoke many personas together in a melting pot). Slow and gentle and somehow sad. ‘Man, I could tell their stories all day’ - Romance in Durango (Desire)
Desire is such a good album. Just go listen to that. From ‘Hot Chilli Peppers in the blistering sun’ to ‘we may not make it through the night’. You can smell and taste this song. - Series of Dreams (Side Tracks)
Underrated track. A thunderous anthology of dream scenes that crests a celestial wave of random fragments. - Belle Isle (Self Portrait)
A man goes for a walk and meets a beautiful maid. - Tin Angel (Tempest)
A long story of violent revenge and sexual jealousy. The delivery and syllable efficiency is what makes this stand out to me. Your imagination has no defence against the final line of each verse.
’He leaned down, cut the electric wire
Stared into the flames and he snorted the fire
Peered through the darkness, caught a glimpse of the two
It was hard to tell for certain who was who’ - Most of the Time (Oh Mercy)
The ultimate ‘sad bastard’ song. Sad bastards love to stew in their misery even when they know better, especially where it concerns love. - Froggie Went a Courtin’ (Good as I Been to You)
This is a cover but links back to my first pick in that I have many memories of it as a child. A 16th Century fable about the political machinations of France toward England but to a child is just a story to imagine.
My favourite Dylan song is Isis.