The 70 Greatest Dylan Songs

27. Sad-Eyed Lady of the Lowlands
Blonde on Blonde (1966)

In his 1976 classic ”˜Sara,’ Dylan explained this song as a tribute to his first wife, whom he had secretly married just months before starting work on Blonde on Blonde. “Staying up for days in the Chelsea Hotel,” he sang wistfully, “writing ”˜Sad-Eyed Lady of the Lowlands’ for you.” Like so many stories about Dylan’s past, the anecdote from ”˜Sara’ is both fascinating and mostly false. ”˜Sad-Eyed Lady of the Lowlands’ is indeed an ode to Sara Dylan, but he largely wrote it on the spot during the dead of night in a Nashville studio. While the session musicians he’d hired played cards, he sat down and wrote the sweetly surreal verses. “It started out as just a little thing,” Dylan said in 1969. “But I got carried away somewhere along the line.” After eight hours of work, Dylan called the band members into the studio at 4 am and gave them minimal instructions. They had no idea the song would keep going for 11 minutes ”“ and they were stunned once more when, afterward, Dylan told them they had nailed it on the very first take.

28. The Times They Are A-Changin’
The Times They Are A-Changin’ (1964)

When people describe Dylan as the “spokesman of a generation,” they are thinking of the man best defined by ”˜The Times They Are A-Changin’.’ And while Dylan would later bluntly reject that title, he consciously sought it with this passionate anthem. A masterpiece of political songwriting, it addresses no specific issue and prescribes no concrete action, but simply observes a world in violent upheaval. (That the song was released just months after the assassination of John F Kennedy only lent it more power.) Dylan sings in the voice of a bard or prophet, in cadences that are clearly biblical ”“ in his words, “short, concise verses that piled up on each other in a hypnotic way.”

29. You Ain’t Goin’ Nowhere
Bob Dylan’s Greatest Hits Vol. II (1971)

How did Dylan spend the Summer of Love? Holed up in a basement in upstate New York, making strange demos with his friends in the Band, singing this stoic warning about tough times ahead: “Strap yourself to the tree with roots/You ain’t goin’ nowhere.” The first time most people outside Big Pink heard ”˜You Ain’t Goin’ Nowhere’ was in the Byrds’ straight country rendition on 1968’s Sweetheart of the Rodeo. Dylan released it three years later as one of the new tracks on his Greatest Hits Vol. II, turning it into a good-time banjo shuffle with his Woodstock pal Happy Traum. He added a sly riposte to the Byrds’ Roger McGuinn: “Gonna see a movie called Gunga Din/Pack up your money, and pull up your tent, McGuinn.” The definitive Basement Tapes version is mysterious, doomy, yet somehow still festive ”“ you can hear Dylan crack up in the final chorus. In an outtake, he sings it as a stoned nonsense lullaby, apparently addressed to his housemates: “Look here, dear soup, you’d best feed the cats/The cats need feeding and you’re the one to do it.” He left the cats out of later versions, but kept the song’s playful spirit.

30. Girl From the North Country
The Freewheelin’ Bob Dylan 1963
By Keith Richards

While the British Invasion was going on, Bob Dylan was the man who really pulled the American point of view back into focus. At the same time, he had been drawing on Anglo-Celtic folk songs, and that’s certainly true of ”˜Girl From the North Country.’ It’s got all the elements of beautiful folk writing without being pretentious. In the lyrics and the melody, there is an absence of Bob’s later cutting edge. There’s none of that resentment. It’s very hard to write songs like that. He recorded it again later with Johnny Cash, but I just don’t think it’s a duo song. I think Bob got it right the first time. In a way, I see ”˜Girl From the North Country,’ ”˜Boots of Spanish Leather’ and ”˜To Ramona’ as a trilogy. Is Ramona the girl from the north country? Is she the same chick who sends the boots of Spanish leather? There’s some connection between them. Also, the guitar picking is almost the same lick in ”˜Boots of Spanish Leather’ and ”˜Girl From the North Country.’ It’s like an extension of the same song. Before he went electric and submitted himself to that relentless discipline of a rhythm section, there was a beautiful flow in Bob’s songs that you can only get with just a voice and a guitar. He can float across the bar here and there. He’s not restricted by anything; it’s a beautiful form of expression. You let certain notes hang longer, and it doesn’t matter because it all goes with the song. He’s the most prolific writer: I think he’s written more songs than I’ve had hot dinners. So, Bob, just keep ’em coming! He’s an inspiration, really, to us all, beyond even the songwriting, because he’s always trying to go somewhere new. I love the man ”“ and I love that he rock & rolls, too!

31. Can You Please Crawl Out Your Window?
Non-Album Single (1965)

Dylan famously kicked folk singer Phil Ochs out of a limousine for saying he didn’t like ”˜Can You Please Crawl Out Your Window?’ In fact, it’s one of Dylan’s great diss tracks. A sequel of sorts to ”˜Like a Rolling Stone,’ the song distils its predecessor’s torrent of contempt down to a taut three and a half minutes of lean, tossed-off spite. The driving, no-frills style came from Levon and the Hawks, backing Dylan in the studio for the first time after playing only a handful of live shows together. But the public wasn’t buying it: ”˜Can You Please Crawl Out Your Window?’ fizzled at Number 58 on the Billboard charts.

32. Chimes of Freedom
Another Side of Bob Dylan (1964)

The most ambitious song Dylan had written to date ”“ a six-verse masterpiece in which a thunderstorm and its lightning flashes become a beacon that summons outlaws, outcasts, artists and “every hung-up person in the whole wide universe” ”“ reportedly evolved out of a brief poem he’d written about John F Kennedy’s assassination in late 1963. Dylan’s gift for internal rhyme and assonance flowered here, as did his knack for phrasemaking: “starry-eyed an’ laughing,” “midnight’s broken toll,” “chained an’ cheated by pursuit.” He first performed it in mid-February 1964, and recorded it that June for Another Side of Bob Dylan (after half a dozen false starts ”“ it’s tough to keep that many lines straight). By the end of the year, he’d dropped ”˜Chimes of Freedom’ from his set, but other artists picked it up and ran: The Byrds recorded it for their first album in 1965, and Bruce Springsteen made it the title track of a 1988 EP.