The 70 Greatest Dylan Songs

20. Blowin’ in the Wind
The Freewheelin’ Bob Dylan (1963)

The song that first branded Dylan a prophet asks nine questions and answers none of them. A rewrite of the anti-slavery spiritual ”˜No More Auction Block,’ Dylan claimed to have knocked out this meditation on humanity’s inhumanity in 10 minutes. The version of the song most people heard in 1963 wasn’t Dylan’s ”“ it was Peter, Paul and Mary’s cover, which hit Number Two on the pop chart. But in any version, the words are so simple, it sounds like they’re handed down from the sky on stone tablets. “It’s absolutely wonderful writing,” says Merle Haggard. “It was timely then and is still timely today.”

21. Mississippi
Love and Theft (2001)
By Sheryl Crow

I released ”˜Mississippi’ before Dylan did, on my album The Globe Sessions. It changed the whole record. There’s no fat in the song ”“ every line has a purpose. He said that he liked every line of his songs to have the possibility of being the first line of a new song. That’s certainly the case with ”˜Mississippi.’ He gets very philosophical about aging, telling a story about redemption and resolution for the everyman in a way that’s almost biblical: “Well, my ship’s been split to splinters and it’s sinkin’ fast/I’m drownin’ in the poison, got no future, got no past/But my heart is not weary, it’s light and it’s free.” It’s Dylan writing like a short-story writer, like Steinbeck or Mark Twain ”“ creating a story, but making these classical, sweeping statements. ”˜Mississippi’ is our introduction to Dylan as somebody facing mortality with an upbeat attitude. Bob Dylan may be turning 70, but he never gets older to me. That’s what mythological characters are all about.

22. Don’t Think Twice, It’s All Right
The Freewheelin’ Bob Dylan (1963)

In 1962, Dylan was heartbroken after Suze Rotolo, his first serious girlfriend, left New York for an open-ended stay in Italy. Out of that pain came this classic breakup ballad, in which he reels from a desperate sense of abandonment to sharp bitterness (“You just kinda wasted my precious time”). “It isn’t a love song,” he wrote in the liner notes to The Freewheelin’ Bob Dylan. “It’s a statement that maybe you can say to make yourself feel better. It’s as if you were talking to yourself.”

Dylan borrowed the song’s melody from folk singer Paul Clayton (who had himself adapted it from the earlier tune ”˜Scarlet Ribbons for Her Hair’), later settling out of court when Clayton filed a claim against him. But a poultry supplier near Dylan and Rotolo’s former Greenwich Village apartment inspired one key image: “When your rooster crows at the break of dawn/Look out your window, and I’ll be gone.” As Rotolo recalled in her 2008 memoir, “When Bob and I stayed up all night”¦ we heard the roosters crowing at the break of dawn.”

23. Forever Young
Planet Waves (1974)

Dylan recorded this folksy prayer twice with the Band ”“ as a sparkling ballad version that closed Side One of Planet Waves, and a stomping country-rock take that kicked off Side Two. Lyrics such as “May you have a strong foundation/When the winds of changes shift” are as universal and uplifting as Dylan has ever written; they also work as a blessing for a generation coming out of a post-Sixties cultural hangover. (Are those the same winds he once suggested the answer is blowin’ in?) Dylan said he wrote it for his son Jesse; others see it as a nod to Neil Young, who scored a Number One hit in 1972 with ”˜Heart of Gold.’

24. Lay, Lady, Lay
Nashville Skyline (1969)
By Lenny Kravitz

I first heard ”˜Lay, Lady, Lay’ when I was six or seven, riding around New York in the back seat of my parents’ old VW Bug, listening to WABC. It was the first Bob Dylan song I remember loving. Later, when I heard another one of his songs, I wondered, “Where’s that low, crooning voice?” He’s singing it in a very different voice from his normal one. I thought this guy sounded like that all the time! It’s a very black song ”“ very soulful and sensual. “Lay across my big brass bed” is a lyric you would expect to hear from Isaac Hayes. The beautiful thing about Dylan is that he is such a chameleon. He’s got so many characters inside of him, like a painter with limitless amounts of colour. I love the vocal. I love the descending chord progression. I love the drum fills. It’s a simple, beautiful love song, and I love the whole feel of it.

25. Knockin’ on Heaven’s Door
Pat Garrett & Billy the Kid (1973)

Always a fan of Westerns (and outlaws of every stripe), Dylan wrote a handful of songs for Sam Peckinpah’s 1973 film Pat Garrett and Billy the Kid. Jerry Fielding, a composer brought in to help Dylan with the music, described his reaction to hearing this heartbreaking sketch of a dying lawman: “It was shit. That was the end for me.” Dylan, of course, had the last laugh. ”˜Knockin’ on Heaven’s Door’ became a Number 12 hit and one of his most-covered songs, with hit versions by both Eric Clapton and Guns n’ Roses. Musically, it’s also one of his simplest compositions ”“ if you can play four easy chords and remember seven lines, you’ve got it down ”“ which may be why, when a guest star shows up for the encore at a Dylan show, this is often the song that gets performed.

26. Masters of War
The Freewheelin’ Bob Dylan (1963)

”˜Masters of War’ is Dylan’s angriest protest song. His starting point seems to be the fears of nuclear holocaust so prevalent in the early Sixties ”“ but characteristically, Dylan took that common theme and gave it a crucial twist. Where typical anti-war songs might indict politicians or generals, Dylan directly challenges arms manufacturers (“You that build the death planes/You that build the big bombs”). His target is the military-industrial complex itself: Greed drives the masters of war, not ideology. “Is your money that good?” Dylan spits out as he envisions a world awash in blood. “Will it buy you forgiveness?” The song ends with the singer calling out for the deaths of those bomb builders, promising to stand over their graves “till I’m sure that you’re dead.” “I don’t sing songs which hope people will die,” Dylan observed at the time. “But I couldn’t help it with this one.”