Every Bob Dylan Album Cover Ranked

The image is swiped from the January 1939 cover of the pulp magazine Spicy-Adventure Stories: a woman in a yellow sarong prepares to break an urn over the head of a bandido strangling another man. Unfortunately, it looks ungainly and amateurish because it’s been squashed from a rectangular composition into a square. Dylan’s never been the poster boy for truth in advertising, but at least the sloppy cover here warned buyers about his same lack of care with the album’s music.

According to painter Tony Wright, this image came directly from a vision Dylan had of Jesus Christ’s hand reaching down to the people of the world. Some album reissues later swapped it out for a different Wright painting of Dylan onstage, either because the first version was too bluntly evangelical or because it looked too much like Christ was attempting to give high-fives to the 2012 Minnesota Timberwolves.

Photographer Al Clayton, describing his encounter with Dylan: “I tried to talk to him, but whenever I would bring up a topic, he would say ‘I don’t know anything about that.’ He was completely withdrawn, and very unto himself.” So maybe it’s not shocking that Clayton didn’t get beyond Dylan’s surfaces with his camera — but it is surprising that those surfaces got garnished with red, yellow, and purple stripes here.

Pretty much the minimum effort possible for a Dylan album cover: Go to your font menu, pick a random typeface, and call it a day. At least it was Goudy Text, not Comic Sans.

Marginally more impressive than Triplicate, both because the typeface choice (a slightly modified version of Plymouth) feels apropos for the soundtrack of a Western, and because when you laid out a title in 1973, you had to work with an X-Acto blade and could cut yourself if you weren’t careful.

Bob Dylan deserves better than stock photos of old playing cards, even when he’s covering “Polka Dots and Moonbeams.”

There are some out-of-focus Dylan covers where the blur adds a veneer of mystery, suggesting the man is, on some level, unknowable. And then there’s this cover, which provokes the sinking feeling that he couldn’t be bothered to spend more than five minutes on a photo session.

Presented for your consideration: a photograph of a statue at a fountain in front of a government building in Vienna. Maybe it’s an effort to give Dylan a high-culture European gloss that could lead to him winning a Nobel Prize one day? It feels more like an outtake from his Victoria’s Secret advertising campaign. Tempest tie-ins that didn’t happen: Dylan dressed up as Prospero; Dylan getting a high score on the 1981 Atari video game; Dylan holding a teapot.

Here Dylan dresses up like an Eighties rock star who gets his videos played on MTV, in a gray suit with rolled-up sleeves and big shoulder pads. (We just want to see if it’s the expensive kind.) This costume doesn’t feel playful: It’s just a craven effort to fit in with the prevailing trends.

This cover showcases a colorized version of a 1964 photo taken in England by Ian Berry. In the past 20 years, the majority of Dylan album covers don’t feature photos of him — and more problematically, they don’t feel like products of his own interests and obsessions. They’re mostly classy, and presumably Dylan signs off on them at some point, but many of them seem to be moves in games of “The Art Director Guesses What’s Going on in Bob’s Head.”

Roy Lichtenstein’s rise to fame in the art world happened at the same time as Dylan’s in music: Between 1961 and 1965, he made a sensation with his pop-art paintings, big on Ben-Day dots and images synthesized from comic books. This cover could be a knowing comment on their parallel careers, but the illustration by Pearl Beach just cops Lichtenstein’s style to no particular end: Like many explosions, this cover is loud without being illuminating.

After the apocalypse comes and the sky has turned red from nuclear fallout, Bob Dylan will be crouched in the wasteland, wearing flashy shoes.

Jimmy Wachtel, formerly a big-time album-cover designer (Bruce Springsteen, Jackson Browne), had moved on to movie posters, but got the call to shoot Dylan. He borrowed a camera and went to Dylan’s Malibu home. He remembered, “I shot one roll and then changed the film — this was prior to digital — and I couldn’t get the film out of the camera. At that point, he said: ‘Maybe we should get another photographer.’ Anyhow, I persevered.” Wanting to jazz up the photo, Wachtel literally gave Dylan the shirt off his back. “I’m sure he could afford his own shirt,” he said. “But I just thought, ‘I’ll give Bob Dylan a gift.’” The cover featured that striped shirt — and the vertical framing of a movie poster.

On the covers of most Dylan albums, his name and the title occupy roughly the same amount of real estate. (Sometimes both are missing altogether.) This one plays down the Infidels title, but announces “BOB DYLAN” like 20 pounds of headlines stapled to the singer’s chest. Those black capital letters have to do all the work of selling the art because Dylan looks grumpy and disconnected. His sunglasses reflect the white stripe of a highway in front of him: He may not know where he’s going, but he’s not staying here.

When Bob Dylan was six years old, this was New York City: bright white lights on Broadway, taxicabs speeding too fast for photographers to capture, electric lights burning all night to bring us one day closer to the future. Ted Croner evoked that energy with this 1947 photograph titled Taxi, New York at Night. How you define the word “modern,” the photo reminds us, may be very different from how Dylan defines it.

Briefly leaving Columbia Records for Asylum, Dylan effectively took over his own art direction, rendering the cover of the album himself in black paint (or possibly ink). He left off his own name but included the messages “moonglow” and “cast-iron songs & torch ballads” — which didn’t catch on as a self-description the way “thin wild mercury music” did. If Dylan intended for the central figure of the cover to represent himself, then he has distinguished himself with a glowing heart on the wrong side of his chest and an anchor weighing down his head.

With a vintage illustration and not the slightest wink, this cover fully commits to the fact that we live in a world where Bob Dylan recorded a Christmas album. If Dylan ever plays Santa Claus in a Christmas movie, a possibility we’re not ruling out, we’re going to insist on it being called Miracle on Positively Fourth Street.

An austere counterpoint to the cover of the Beatles’ Sgt. Pepper’s Lonely Hearts Club Band, which came out earlier the same year and featured Dylan in the platoon of cardboard celebrities joining the Beatles on the cover. Here, Dylan stands next to Purna and Luxman Das, who were musician-scholar-mystics in the Baul tradition of Bengal, India — and the carpenter Charlie Joy. (Whoever was squatting in the front, with a white cowboy hat, got cropped out and has been lost to history.) “It was the coldest day of the year,” photographer John Berg (also the art director of Columbia Records) told the website Untold Dylan. “It was like 20 below zero. It was so cold that we ran outside — the Bauls, the woodworker, and whoever else were there — took pictures until it was no longer possible, and then rushed back in for a brandy.”

Columbia Records and Dylan couldn’t agree on how to present his first album after his conversion to Christianity, so by the time the assignment came to illustrator Catherine Kanner, she had just one day to draw an acceptable cover image, with graphic designer Bill Stetz literally looking over her shoulder. Dylan himself requested the train and the man with the ax. “In my original sketch, I rendered the ax as it would naturally be,” she said, but Stetz insisted “that I extend the top of the ax so it more resembled a cross.”

The photograph is a striking 1959 Bruce Davidson picture of a couple making out in the backseat of a car. It evokes Dylan’s Never Ending Tour and his life on the road: The car is in motion, but time stands still for two young entwined lovers. The barbed moral for an aging songwriter is that in order to see the passion in the back seat, you can’t be looking at the road ahead. 

This blurry photo, taken by album producer Daniel Lanois, captures the truth of how Dylan has spent many of his days and nights: in a recording studio. He holds the acoustic guitar like it’s a shield; state-of-the-art recording technology surrounds him like battlements.

If a painting by Bob Dylan appears on the cover of an album called Self Portrait but doesn’t much look like him, does that mean that he’s not a very good painter? That he sees himself differently than we do? That he was actually painting somebody else and the joke is on us for trying to connect the art with the man?

The cover is a still from the movie Shadow Kingdom: The Early Songs of Bob Dylan, an arty black-and-white concert film directed by Alma Har’el. With a pretentious mood and a face disappearing into a penumbra, Dylan makes a case for himself here as the secret king of goth. 

Earnest, bearded, calm: While Dylan survived for years on cigarettes and obstinance, here he looks like a man who just took up yoga and did a juice cleanse.

For this collection of standards from the American songbook, art director Geoff Gans provided a witty album cover: It’s a package from the alternate universe where Dylan spent his career as the flagship jazz crooner on Blue Note Records.

For many years, standard operating procedure for photographers assigned a Dylan album cover was to go for a walk with him and see what happened. The Popspots website reconstructed the journey of Dylan with photographer Sandy Speiser on the cover shoot for his fourth album: They walked around midtown Manhattan, stopping to pose in front of a novelty gift store displaying masks of Jackie Kennedy and Charles de Gaulle and to shoot a rifle in an arcade. On the corner of Broadway and 52nd Street, Dylan posed with one leg hitched up on a lamppost, just one more New Yorker alone in his own thoughts in the middle of a crowd.

With no time for a photograph, Dylan recommended a mural by the artist Remerro Trotsky Williams, called “Dancing Couple,” that he had spotted on a wall next to a Chinese restaurant, near the Power Station recording studio in New York City. The painting is spontaneous but rendered on brick; its subjects appear to be more emotionally connected to the music they’re hearing than to each other. In other words, the photo of the mural works here because it evokes some of Dylan’s own contradictions.

Dylan, just 20 years old, poses uncertainly for photographer Don Hunstein in a sheepskin jacket and a sailor’s cap. The photo is flipped for this cover so as not to obscure the Columbia Records logo in the upper-left-hand corner — but it still captures the moment just before Dylan figured out who he was.

To get this shot of Dylan looking soulful and mustachioed, photographer Kevin Mazur hung out during the sessions for the album, trying to stay invisible until the right moment presented itself. As he told the story, “Bob at one point during the recording said to someone, ‘Hey, man, I think you should have Kevin come in and take photos.’ And I was hiding behind a road case. I popped out, and I said, ‘I’m right here, Bob.’ He jumped. I scared the shit out of him.”

That’s not a painting of Bob Dylan: It’s a photograph taken by Paul Till from the audience of a 1974 concert at the Maple Leaf Gardens in Toronto. Till used a darkroom technique called the Sabattier effect that produced a type of double exposure (both a positive image and a negative image), and then hand-colored it. He looked up the address of Dylan’s management in Who’s Who and mailed off a copy of the photo. “I would have been pleased just to get a letter back,” he said, but instead found his image on the cover of Dylan’s next album. The result: “After the Blood on the Tracks photos, I figured that I’d be a professional photographer.”

Dylan photographed by Howard Alk on the streets of Santa Monica: sleeves rolled up, looking for action, conspicuously not wearing his wedding ring.

In 1969, Dylan smiling felt like a radical, openhearted act. According to photographer Elliott Landy, this picture was taken not in Nashville, but in Woodstock, New York. From Landy’s book Woodstock Vision: “‘Do you think I should wear this?’ he asked, starting to put on his hat, smiling because it was kind of a goof, and he was having fun visualizing himself in this silly-looking traditional hat. “‘I don’t know,’ I said as I snapped the shutter. It all happened so fast. If I had had any resistance in me, I would have missed the photograph that became the cover of Nashville Skyline. It is best to be open to life.”

Dylan woke up Dave Stewart (of the Eurythmics) at 4 a.m. and asked him to organize a video shoot that day for his song “Blood in My Eyes.” Stewart agreed and a few hours later led him on a picaresque tour of London, shooting him with an 8 mm camera. Dylan was wearing a top hat and cheerfully interacting with strangers; Stewart judged the day to be sufficiently surreal to require further documentation, so he called his unflappable friend, the Colombian photographer Ana María Vélez Wood, who only 48 hours earlier had been in the Amazon jungle. In a Camden Town café, she took the photo that became the World Gone Wrong cover: an improvised shot that looked as if it had been carefully staged to show a man of a bygone age whose candle had not yet burned to the wick.

How to capture the anarchic spirit of these famous and often-bootlegged (but not photographed) sessions? For their release, eight years after they were recorded, Dylan and the Band recruited photographer Reid Miles because they liked his album cover for Thelonious Monk’s 1968 album Underground. This cover was shot in the basement of the Hollywood YMCA; the musicians were joined by people costumed as circus performers and characters from the songs, such as “Quinn the Eskimo.” To add to the Fellini-esque tableau, Dylan and the Band dressed up too, some wearing military uniforms. Because the songs were intended as demos for other performers, the album and its cover both have the playful spirit of a Halloween party. Sometimes music can be a costume of its own.

One year earlier, Dylan and photographer Barry Feinstein had road-tripped together from Denver to New York, driving a Rolls-Royce belonging to Dylan’s manager Albert Grossman. (A photo of Dylan’s feet sticking out the window of the Rolls-Royce ended up on the cover of the 1970 album Delaney & Bonnie & Friends on Tour With Eric Clapton.) So Dylan trusted Feinstein when the photographer took him to a friend’s penthouse apartment in New York City and shot Dylan on the balcony, looking chiseled and intense. In his book Real Moments, Feinstein wrote, “I didn’t have to shoot a lot of pictures because I knew immediately it was a very unusual shot and an angle and a moment with Bob.”

This brown leather jacket makes the first of its three appearances on Dylan albums: It’ll be seen again on John Wesley Harding and Nashville Skyline. The jacket wasn’t particularly warm, which was a problem on the cold winter day when Dylan and photographer Jerry Schatzberg walked around the Meatpacking District of New York City for this cover. They were both shivering from the cold, which is why this photo is out of focus: Schatzberg was having trouble holding the camera steady. That blur, however, gave the shot a slightly enigmatic, hallucinogenic feel. Schatzberg figured that Columbia Records would never opt for an out-of-focus photo, but Dylan insisted on it. “That was great,” Schatzberg said. “Because usually what Bobby wants, Bobby gets.”

By Ken Regan’s count, he took 13,750 photos of Dylan and his collaborators on the Rolling Thunder Revue. The shot used for the cover of Desire came on the first day of the tour, and it shows Dylan looking fabulous: gray felt hat, scarf, coat with a fur collar. Sure, on the cover of his 1970 solo album, John Phillips wore an incredibly similar outfit. But Dylan won the “Who Wore It Best?” contest because he looked like he was about to explore the United States as a particularly dissolute member of the Lewis and Clark expedition.

Dylan sits on the steps outside the Gramercy Park apartment of Albert Grossman, with his pal Bob Neuwirth enlisted by photographer Daniel Kramer to fill out the frame. “This wasn’t the plan,” Kramer told Rolling Stone. “This wasn’t even expected, that we would do a picture like this.” Even with his hair looking like a Q-tip, Dylan’s the epitome of cool here. He’s got a silk shirt over a Triumph Motorcycles T-shirt, his sunglasses in his hand, a confrontational glare that goes electric all by itself. But it’s Neuwirth who makes the photo with his borrowed camera: We’re not just looking at a portrait of a singer — we’re somehow witnessing a moment where the photo is about to happen, like we’re standing on the edge of history.

A treasure hunt inside a whirlpool of consciousness. Dylan poses with a cat (named Rolling Stone or Lord Growing, depending on who you ask) and Sally Grossman (Albert’s wife). They are surrounded by mid-Sixties cultural flotsam: books, pamphlets, magazines with pictures of Lyndon Johnson and Jean Harlow, a fallout shelter sign, cufflinks (a gift from Joan Baez), and LPs by Robert Johnson, Ravi Shankar, Lotte Lenya, Eric Von Schmidt, and the Impressions. Dylan’s previous album, Another Side of Bob Dylan, is pointedly placed at the back, as far away from the camera as possible. Photographer Daniel Kramer created the fisheye-lens effect with a double exposure, rotating the camera around so the world blurred for everybody except Dylan, who gazes into the lens, accepting that he is at the center of the universe. Kramer took hours to get 10 shots: The cover is the only one where Dylan, Grossman, and the cat were all looking into the camera at the same time.

Bob Dylan walks down a slushy street in Greenwich Village, reunited with his girlfriend Suze Rotolo, back in New York City after a sojourn studying in Italy. Photographer Don Hunstein captured this image, full of love and art and the endless possibilities of youth. (Cameron Crowe memorably restaged it with Tom Cruise and Penelope Cruz in the 2001 movie Vanilla Sky.) According to Rotolo, she and Dylan were both extremely cold: “I had on a couple of sweaters, the last one was his, a big bulky knit sweater,” she said. “So I always look that picture as I feel like an Italian sausage because I had so many layers on, and he was freezing and I was freezing and had more clothes on.” She and Dylan both learned young how much distance there could be between image and reality — and how it was often worth making a memorable image anyway.