In his prime, Bob Dylan wrote about love like no one else could. Things don't always end well, and Dylan often embraces that reality in his songs about relationships. That's what helps them feel so grounded, and his unique turns of phrase echo throughout music history. Then there's the music itself, of course, which can have a fairly wide range but usually works best when an acoustic guitar is at the helm. There's just something about Dylan's voice in a folk aesthetic that can pierce the soul so incisively.
"Boots of Spanish Leather" and "Girl from the North Country" are both lovely examples of Dylan's somber finger-style mode, and it wouldn't be surprising to see an average fan include one or both of them on their own top 10 (though they're too similar to another Dylan classic for this writer to do that). Then there's the very different "Lay Lady Lay," with its slide guitar and Dylan's notably different voice, and "Wedding Song" is an underrated acoustic number from the mid-70s. Dylan's greatest love songs are absolute knockouts, and they can vary significantly in tone. We're ranking them based on their emotional power, storytelling prowess, and encapsulations of what love (or lack there of) can do to the soul.
10 "All I Really Want to Do"
'Another Side of Bob Dylan' (1964)
Let's start with a funny one. Bob Dylan loves a good list, and "All I Really Want to Do" is one of his best ones. In every verse, he lists all the things that he doesn't want to do to a woman. He mentions a bunch of tropes mentioned in songs and the public discourse at large—from simplifying her to mistreating her to meeting her family—poking fun at all these unoriginal expressions of affection to make his own stand out.
"All I Really Want to Do" is a sort of anti-love song, a parody of what all these other people say or do when writing about women. While Dylan's speaker definitely wants to be more than friends, the message that a lover should be a friend and equal is as clear as his yodeling. As an acoustic song, this has the typical guitar/harmonica setup, but Dylan is notably laughing throughout. We can hear that he's having a good time, which makes the listener enjoy this playful piece even more.
9 "Simple Twist of Fate"
'Blood on the Tracks' (1975)
"Simple Twist of Fate" is one of the lighter acoustic pieces from Blood on the Tracks, but there's still an undertone of loneliness that's palpable throughout the whole thing. It's most pronounced in the introduction, though, when we're working only with the softly strummed guitar. Dylan's voice complicates things, what with those rhyming couplets and tonally diverse delivery—which always ends in a delightful apex. It's not quite the yodel in the previous entry, but the way he raises his voice for a word that rhymes with "fate" in the chorus (in total juxtaposition to his normal tone) proves very effective.
The harmonica half-way through the song is a nice break from the story, and the harmonica in the outro is just as pleasant. Like the rest of the songs on this album, the lyrics here set every scene so well. When we hear that he "pushed the window open wide / felt an emptiness inside," we feel like we're there too.
8 "Lily Rosemary and the Jack of Hearts"
'The Bootleg Series, Vol. 14: More Blood, More Tracks' (2018)
The second entry in a row from Blood on the Tracks, except the best version of "Lily, Rosemary and the Jack of Hearts" was released on the 19th volume of The Bootleg Series. It took a while, but like all of Dylan's precious bootlegs, it's worth the wait. Lyrically, the track is very cinematic, as Dylan sets the scene of the end of a carnival before directing our focus on one of the main characters: "he was standin' in the doorway, lookin' like the Jack of Hearts."
It's interesting how we shift perspectives from character to character: the Jack of Hearts, Lily, Rosemary, the backstage manager, etc. With enough room to give people like Big Jim a backstory, this song movingly builds up to two different murders, a robbery, and lovers who don't wind up together. This version is ten minutes long, but these captivating minutes really fly by.
7 "Don't Think Twice, It's Alright"
'The Freewheelin' Bob Dylan' (1963)
You can tell how old this song is by the sound quality. "Don't Think Twice, It's Alright" came out on Dylan's 1963 breakout record, The Freewheelin' Bob Dylan, so the guitar sounds a bit rougher than what's expected of popular music today. But that kind of just helps with the overall tone, like an extended goodbye. The Travis picking, the harmonica breaks—they're all perfectly crafted to bring a tear to the listener's eye. Without even hearing the lyrics, it's no wonder this became one of Dylan's breakout songs.
Of course, everything is enhanced once you listen to the words. Expressions such as "It ain't no use to sit and wonder why, babe, if you don't know by now" and "I can't hear you anymore" add so much texture. There is a tinge of bitterness here, yet the tone is largely more thoughtful and forgiving. While he says that she wasted his time, which most fans can relate to, he reminds her to not think about it too much. Or, to be specific, "Don't think twice; it's all right."
6 "Buckets of Rain"
'Blood on the Tracks' (1975)
There are the Bob Dylan acoustic songs that are driven by chords, and then there are the ones driven by gorgeous riffs. "Buckets of Rain" is one of the latter, and among the best of them. Yet another from Blood on the Tracks (except this isn't a Bootleg version), "Buckets of Rain" actually feels more like a sun shower. The first thing we hear is that guitar hook, and we never get tired of it over the course of these three and a half minutes. This riff is so strong, in fact, that it drives both the verse and the chorus.
If you even want to call it a chorus; this is more like how old folk blues songs by such artists as Mississippi John Hurt would just pick the same thing over and over, alternating between singing through one round and then letting the guitar speak for itself after. "Buckets of Rain" isn't bluesy, but it definitely has the combination of sadness and warmth you can find in that genre. Another difference of course would be that bass, which fits in as well as always.
5 "It Ain't Me, Babe"
'Another Side of Bob Dylan' (1964)
There's no discernible bass in this one: just Dylan's voice, guitar, and harmonica. That's all we really need, and "It Ain't Me, Babe" is one of the most powerful examples of that. The common expression "It's not you, it's me" is more or less the argument that this narrator takes on, even though the title on the surface might make one think the opposite at first. A girl is in love with him, but he hammers home the point—in as many ways as he possibly can—that he's just not the guy she wants.
There really is no one who can beat Dylan when it comes to these sad love songs. The way he sings this, it sounds like the speaker regrets the fact that he can't be the kind of "someone to close his eyes for you, someone to close his heart" that she wants. After all, his attitude could have been more flippant or humorous. In contrast, this comes across as constant, somber self-criticism. Overall, the tone and lyrics meld together so well that the song is hard to shake off.
4 "You're Gonna Make Me Lonesome When You Go"
'Blood on the Tracks' (1975)
"You're Gonna Make Me Lonesome When You Go" is tonally and lyrically the antithesis of the previous entry. This time the narrator is very much enamored with a woman who's leaving him, but he also doesn't dwell in self-pity. This is far from this guy's first rodeo ("Relationships have all been bad"), and it feels like he's still so happy from the time he spent with this unnamed former lover that the melancholy hasn't set in yet. As Dylan sings, "I could stay with you forever and never even realize the time," there is pure joy in that thought.
"You're gonna make me give myself a good talkin' to" and wondering what he's doing is yet to come. That's partly because he still sees her in the sky, in the grass, and tells himself that he'll look for her. This is a breezy, concise three minutes of Dylan in one of his most enthusiastic performances of the 70s. That bass supports the breathless tempo as well as you'd expect from Blood on the Tracks, leaving fans to wonder how he makes break-up songs sound so effortless.
3 "Tomorrow is a Long Time"
'Bob Dylan's Greatest Hits: Vol. II' (1971)
Back to another solemn one. "Tomorrow Is a Long Time" is one of those pieces that Dylan wrote when he was really young but didn't release formally until much later. In this case, it came out on not his first but his second greatest-hits album. Imagine being such an icon that masterpieces like this get placed on the back-burner for the better part of a decade. It's a crazy move from a listener's perspective, as most songwriters would kill to write something this good. (However, it does seem like he borrowed the guitar section for such titles as "Girl from the North Country" and "Boots of Spanish Leather.")
Anyway, the fingerpicking here is heavenly. It's fascinating how the C and G chords are so common in popular music, and yet can still pull so much weight without feeling like they're overused. At least in the right hands, including and especially Bob Dylan's. Along with lyrics that basically wander through hypotheticals that highlight just how lonely the speaker is, "Tomorrow is a Long Time" is almost too heavy to bear.
2 "If You See Her, Say Hello"
'The Bootleg Series, Volumes 1-3 (Rare & Unreleased) 1961-1991' (1991)
The New York recordings for Blood on the Tracks dominate this list, as they should. One of its greatest pieces, "If You See Her, Say Hello" recounts a falling out that "still brings me a chill." While the electric version's sunny guitars and light percussion may appeal to many fans, it waters down the raw emotion in the acoustic version to the point where that "chill" isn't really there (especially in how he draws that word out annoyingly long).
It doesn't feel like Dylan knows exactly what to do with this pace in Blood on the Tracks, stretching many other words out so far that they lose their personality and any trace of the tragedy the words are trying to tell. The words are spoken more quickly in this acoustic iteration—spoken naturally, with the complicated tone that reflects an achingly sad story of a man who can't stop thinking about his ex.
1 "Tangled Up in Blue"
'The Bootleg Series, Volumes 1-3 (Rare & Unreleased) 1961-1991' (1991)
Dylan's crowning achievement of Blood on the Tracks: "Tangled Up in Blue." But not the version that most people know. Even the introduction to this version from The Bootleg Series (specifically Take 3, Remake 2) sounds nothing like the one we hear in Blood on the Tracks. Fans only familiar with the popular recording would only recognize this predecessor from its lyrics, which aren't all the same but nevertheless make up one of Dylan's best love stories.
What we get is a love triangle, between a "she," a "he," and an "I." We get fragments, summaries, scenes of these unnamed people—how they met, how they split up—a mood of bittersweet nostalgia that inhabits an almost mythical quality as the piece goes on. It's interesting how the narrator only becomes a part of the story in the fourth verse, and there are so many great one-liners that you can throw a dart and land on a winner. For this entry, let's go with: "We always did feel the same; we just saw it from a different point of view. Tangled up in blue."
English (US) ·