In 1961, 19-year-old Robert Allen Zimmerman dropped out of college in his native Minnesota, made a pilgrimage to New York City to meet his folk music idol Woody Guthrie, and decided to become, in his own words, “Guthrie’s greatest disciple.” Performing in Greenwich Village as Bob Dylan and then signing to Columbia Records, he achieved his goal in short order, becoming the most famous folk singer in America by 1964.

Newport Folk Festival, Newport, Rhode Island, July 1963. (Credit: Rowland Scherman/Getty Images)

Dylan first performed with an electric guitar and full backing band at the 1965 Newport Folk Festival, provoking backlash from many in the folk music community. With hits like “Like a Rolling Stone” and “Rainy Day Women #12 & 35,” though, Dylan became a bona fide pop star, and became the voice of his generation.

More from Spin:

The 5 Best Overlooked Films of 2024

Album of the Year: The Cure’s ‘Songs of a Lost World’

Honey, I Think I Shrunk Gen X

Following a 1966 motorcycle crash, Dylan withdrew from the public and didn’t tour for eight years, but continued to release albums that sometimes baffled fans, such as Self Portrait. For the next few decades, Dylan would periodically seem  spent, yet then release a brilliant album that returned him to prominence like 1975’s Blood on the Tracks or 1997’s Time Out of Mind

Massachusetts, April 1964. (Credit: John Byrne Cooke Estate/Getty Images)

Since 1988, Dylan has performed over 3000 concerts on what’s been dubbed his Never Ending Tour, while continuing to record albums that add to his legacy as America’s most revered songwriter.

Although he has been the subject of films and documentaries over his career, A Complete Unknown represents the first conventional, big budget Dylan biopic produced with hiss approval. As filmgoers flock to see Timothee Chalamet dramatize Dylan’s fabled early years, let’s take a look back at his immense and immensely influential catalog. Oh, and rank them.

40. Under the Red Sky (1990)

Many Dylan sidemen have become stars, from Al Kooper to Robbie Robertson, but nobody listens to a Dylan album for guest stars. Elton John, Slash, Stevie Ray Vaughan, George Harrison, and David Crosby are just a few of the big names who pass through on the star-studded Under the Red Sky, rarely making recognizable or worthwhile contributions to a set of songs that frequently reference nursery rhymes. Kooper himself shows up to imitate his own iconic “Like a Rolling Stone” organ line on a deeply mediocre song called “Handy Dandy.” Under the Red Sky’s opening track “Wiggle Wiggle” (“wiggle wiggle wiggle like a bowl of soup”) regularly appears on lists of the worst Dylan songs or the worst songs by great artists.

39. Self Portrait (1970)

The idea that a double LP, which by necessity commanded about twice as much of a listener’s time and money, should be a major artistic statement was cemented partly by Dylan himself on Blonde on Blonde. So it felt like Dylan had broken that informal social contract four years later with Self Portrait, a diffuse and indifferent double album that makes his “country crooner” voice from Nashville Skyline sound even stranger and sillier when deployed in between songs with more conventional Dylan vocals. Dylan covering Simon & Garfunkel’s “The Boxer” should be an event, but he haphazardly layers two vocal takes that stumble all over each other, rendering the track unlistenable. The jaunty, wordless “Wigwam,” used to great effect in Wes Anderson’s The Royal Tenenbaums, is an example of how Self Portrait can actually be quite pleasant to listen to at times, but also how devoid of meaning or purpose it is compared to Dylan’s best work. “What is this shit?” was how Greil Marcus chose to open his famously incensed Rolling Stone review of Self Portrait.

38. Empire Burlesque (1985)

In 1985, Bob Dylan was among the dozens of stars that united on the charity single “We Are the World,” which ultimately became the only song involving Dylan to hit No. 1 on the Hot 100. Empire Burlesque, released weeks after the song’s chart reign, almost sounds bright and polished enough to capitalize on that moment, but the mediocre songs sank Dylan deeper into his ’80s rut. The first two songs, “Tight Connection to My Heart” and “Seeing the Real You at Last,” both freely quote and paraphrase dialogue from multiple Humphrey Bogart movies. Even Dylan’s blander albums contain fascinating quirks like that.

37. Pat Garrett & Billy the Kid (1973)

Dylan took a small acting role in Sam Peckinpah’s Pat Garrett & The Billy the Kid, and also scored the film. By the time the soundtrack album was released, Dylan had decided not to renew his contract with longtime label Columbia and jump to the newly formed Asylum Records. His unintentional parting gift to Columbia was “Knockin’ on Heaven’s Door,” which stands as by far Dylan’s most streamed song half a century later. The rest of the Pat Garrett soundtrack, however, is mostly pleasant but inconsequential instrumental sketches.

36. Dylan (1973)

Dylan is the only official Dylan studio album that was assembled without his input—Columbia released it after he’d left the label, rushing Dylan into stores two months ahead of his Asylum debut, Planet Waves. Comprised of New Morning and Self Portrait outtakes, Dylan is probably a more commercially savvy album than Dylan himself would have ever chosen to release, with several covers of contemporary hit songs. The rendition of Elvis Presley’s “Can’t Help Falling In Love” is wonderful, but covers of Joni Mitchell’s “Big Yellow Taxi” and Jerry Jeff Walker’s “Mr. Bojangles” are weak. At least the album has great cover art designed by John Berg, who was also responsible for the iconic cover of Dylan’s 1967 Greatest Hits compilation.

35. Shot of Love (1981)

The Bob Dylan that the world fell in love with was a thinker, a joker, a fighter, and sometimes a lover. When he converted to Christianity and recorded a trio of gospel albums in the late ’70s and early ’80s, some fans found it harder to accept Dylan as a believer. There’s just something about hearing one of popular music’s great philosophers sing piously about salvation that felt strange. “Lenny Bruce” may be the worst song Dylan ever wrote about a public figure, with a book-report blandness at odds with the subject of the song.

34. Good As I Been to You (1992)

After the embarrassment of Under the Red Sky, Dylan returned to his roots with a solo acoustic album of folk and blues covers. Some of Dylan’s vocal performances on Good As I Been to You are lovely, particularly “Canadee-i-o” and “Tomorrow Night,” but it’s hard not to hear the album as a retreat on some level. A month after Good as I Been to You was released, Dylan and a huge assemblage of stars performed at Madison Square Garden for the 30th Anniversary Concert Celebration, an event that almost exclusively featured songs from the first 10 years of Dylan’s career.

33. Down in the Groove (1988)

Down in the Groove is one of the more truly strange anything-goes albums of Dylan’s career. The Brooklyn hip-hop crew Full Force provide harmonies on the gorgeous acoustic “Death Is Not the End,” and a few tracks later, the Grateful Dead sing on “Silvio,” co-written by longtime Dead lyricist Robert Hunter. Drawn from sessions over a period of five years, Down in the Groove was commercially unsuccessful and critically panned, but by the end of the year Dylan was on an upswing with the release of the Traveling Wilburys’ multiplatinum debut. Former President Barack Obama included “Silvio” on his annual summer Spotify playlist in 2024, and weeks later Dylan performed the song for the first time in more than 20 years.

32. Shadow Kingdom (2023)

When Dylan’s Never Ending Tour took some time off in the early 2020s amidst the COVID-19 pandemic, he performed with a group of masked musicians in director Alma Har’el’s film Shadow Kingdom: The Early Songs of Bob Dylan. The Shadow Kingdom soundtrack differs from many late-period Dylan live albums in that it features him singing some of his best known songs in recognizable arrangements. That said, it’s a rare example of Dylan backed by a full band with no drummer, and it can be frustrating to listen to lively renditions of “Most Likely You Go Your Way (And I’ll Go Mine)” and “I’ll Be Your Baby Tonight” that are just begging for a strong backbeat.  

31. Shadows in the Night (2015)

Frank Sinatra and Bob Dylan were both transformative figures of 20th century pop music, and on paper they’re opposites: the romantic jazz crooner and craggy-voiced folk songwriter. There’s not an insignificant shared territory in their taste in material, though, and unsurprisingly Dylan’s first Ol’ Blue Eyes tribute album goes heavy on Sinatra’s “saloon songs” on Shadows in the Night with selections like “I’m a Fool To Want You” and “Why Try To Change Me Now.” Donnie Herron’s pedal steel guitar really brings “Some Enchanted Evening” and “Full Moon and Empty Arms” to life, taking the place of a string section in Dylan’s pared down arrangements.

30. Fallen Angels (2016)

15 months after Shadows in the Night, Dylan returned with another collection of pop standards that had mostly been made famous by Sinatra. Fallen Angels leans a little more towards universally recognizable songs like “Young at Heart” and “It Had to Be You,” and there’s a certain charm in hearing a septuagenarian Dylan really reach for high notes he’d ordinarily decline to attempt. I don’t have a problem with Dylan recording two Sinatra tribute albums in the last 10 years—so did Willie Nelson—but Nelson’s were better. “In so many of these tracks—the rosy-cheeked ‘Polkadots And Moonbeams’ and the sublime violin-aided take on Hoagy Carmichael and Johnny Mercer’s masterful ‘Skylark’—it’s Dylan moving gently and gracefully through material he obviously loves,” Kenneth Partridge wrote in the A.V. Club review of Fallen Angels.

29. Triplicate (2017)

For the third year in a row, Dylan raided the Great American Songbook, this time with a 30-song triple album, and received his third consecutive Grammy nomination for Best Traditional Pop Vocal Album. At this point some fans began to wonder if he’d ever return to recording original material, and had to wait three more years to get their answer. As his longest studio album, though, Triplicate is the final argument that this was not a side quest but a major creative project for Dylan, as much a celebration of his own voice as the songwriting of legends like Irving Berlin and Hoagy Carmichael. The way Dylan repeatedly chuckles to himself on “Braggin’” feels like a moment of joy he’s sharing with the listener.

28. Knocked Out Loaded (1986)

Bob Dylan toured extensively with Tom Petty in 1986, with Dylan backed by Petty’s band the Heartbreakers. The two legends began writing together during the tour, planting some of the seeds of what would eventually become the Traveling Wilburys. Their first co-write, “Got My Mind Made Up,” isn’t great, but it’s at least better than the Dylan/Petty composition that wound up on Petty’s next album, “Jammin’ Me.” Knocked Out Loaded consists of eight songs, only two of them written solely by Dylan, and he sometimes sounds as bereft of inspiration as he ever has. The exception that saves the album is “Brownsville Girl,” an 11-minute song co-written with playwright Sam Shepard that contains some of Dylan’s funniest lyrics ever and multiple tangents about actor Gregory Peck.  

27. Saved (1980)

“Pressing On” is one of the best songs of Dylan’s Christian period, and the sincerity of his vocal is moving. The rest of Saved, however, doesn’t always have the same magic, and too many songs are drowned in loud gospel-backing vocals. Legendary session drummer Jim Keltner, who’d first worked with Dylan on “Knockin’ On Heaven’s Door,” had joined Dylan’s touring band by 1980, and Saved was the first of several Dylan albums with Keltner on drums, including Empire Burlesque and Time Out of Mind.

26. Christmas in the Heart (2009)

If Bob Dylan had recorded his first and only Christmas album in the early ’80s, Jesus Christ probably would’ve been the focal point of the album. Dylan recorded Christmas in the Heart in 2009, though, and the main character is Saint Nick, celebrated both in the opener “Here Comes Santa Claus” and a raucous rendition of “Must Be Santa.” Dylan has produced most of his later albums under the pseudonym Jack Frost, never more appropriately than on this surprisingly delightful collection.

25. Together Through Life (2009)

Dylan co-wrote two songs with Grateful Dead lyricist Robert Hunter on Down in the Groove, shortly after his 1987 tour with the Dead. Two decades later, Hunter became one of the few people to co-write an entire album with Dylan, credited on nine out of 10 tracks on Together Through Life. Dedicated Dylanites and Deadheads could probably analyze who wrote what lines on the album all day, but Dylan and Hunter seem to share the same sense of humor on droll songs like “My Wife’s Home Town” and “Shake Shake Mama.”

24. Bob Dylan (1962)

It might seem strange that one of the most revered songwriters of all time only penned two original songs on his debut album. Dylan had to exhaustively learn and perform the American folk music canon before he could add to it, though. One of those two songs, “Song to Woody,” was dedicated to his idol, Woody Guthrie, who, afflicted with Huntington’s Disease, Dylan began visiting in the hospital year earlier. The self-titled album is a fascinating study in how thoroughly the 20-year-old singer had developed his vocal style and his public persona at that point, even if he’d only just begun to actually write songs. His rendition of “In My Time of Dyin’” has an eerie power, and the arrangement of “House of the Risin’ Sun” that Dylan learned from Dave Van Ronk would within two years become a massive pop hit for the Animals.

23. World Gone Wrong (1993)

World Gone Wrong doesn’t turn the clock back 30 years to when Dylan was performing in Greenwich Village clubs. But Dylan, at home in his garage with a recording engineer as his only company, taps right back into the potent emotion and drama of the folk and blues that he started his career playing. The simpler recording setup and selections like “Blood in My Eyes” and “Delia” help make World Gone Wrong far more viscerally affecting than its predecessor from a year earlier, Good As I Been to You.

22. Slow Train Coming (1979)

The first song Dylan released as an evangelical Christian, “Gotta Serve Somebody,” was an unqualified success, a Top 40 hit that won a Grammy. Dylan’s Christian era was pretty much all downhill from there, but “Precious Angel” and Slow Train Coming’s title track benefit greatly from guitar licks from Dylan’s new sideman, Mark Knopfler of Dire Straits. 

21. Rough and Rowdy Ways (2020)

The first three songs on Rough and Rowdy Ways feature dozens of first-person statements starting with the word “I,” many of them florid boasts like “I carry four pistols and two large knives” or “I can see the history of the whole human race.” On his most recent collection of new songs, a 79-year-old Dylan is feisty and defiant, almost mocking all the analysis of what he reveals about himself in his lyrics. The album ends with his longest studio track ever, “Murder Most Foul,” a staggeringly ambitious, but also funny and tangential, 17-minute survey of American history since the JFK assassination.

20. Nashville Skyline (1969)

The “Bob Dylan” that the public met in the early ’60s was largely a fabrication, from the name to the voice. So it made some sense that Dylan felt he could simply reinvent himself and begin singing in a completely different voice, a contrived country croon, at the end of the decade. Nashville Skyline feels like a strange detour, perhaps even more now than it did at the time, but there’s an undeniable charm to “Girl from the North Country” with Johnny Cash and “Lay Lady Lay,” consistently two of Dylan’s most popular songs in the streaming era.

19. Infidels (1983)

Infidels was Dylan’s return to secular music after three albums of preaching Christian gospel, and it was greeted by fans and critics with a sigh of relief. Dylan hired Slow Train Coming guitarist Mark Knopfler to produce Infidels, and the band, including Jamaican rhythm section Sly & Robbie and former Rolling Stones guitarist Mick Taylor, backs Dylan with stately rock and a little reggae. Dylan didn’t tour in support of Infidels, but performed “Jokerman” and “License to Kill” in a memorable 1984 appearance on Late Night with David Letterman, backed by the Latino punk band the Plugz.

18. Love and Theft (2001)

It’s a relatively minor makeover in a career full of reinvention, but the mustache that Dylan sports on the cover of Love and Theft, which he’d continue wearing for the next few years, was like an emblem of the sound of the album. Songs like “Mississippi” and “Lonesome Day Blues” feel like they could be sung by the gunslinger or riverboat gambler that Dylan resembled at the time. “The real star of Love and Theft is Dylan’s voice. Dylan’s golden throat has been a punchline for four decades now, but there is truly no precedent for the unpolished rasp captured here,” Alan Light wrote in the SPIN review of the album.

17. Desire (1976)

Scarlet Rivera was crossing the street in Greenwich Village with a violin case in 1975 when Bob Dylan invited her to a rehearsal studio where he was preparing for the Rolling Thunder Revue tours. Rivera’s violin wound up being a defining feature on Desire, perhaps to a greater extent than any other instrumentalist on a Dylan album. Dylan wrote most of Desire with theatre director Jacques Levy, including the hit “Hurricane” that protested the murder conviction of boxer Rubin Carter, and it was Dylan’s last multiplatinum album in America, the end of his era of commercial dominance.

16. Street-Legal (1978)

Dylan went through a rough patch in 1977 and 1978, including a divorce and custody battle with his first wife Sara, who co-starred in his directorial film debut Renaldo and Clara, which was panned. Music critics weren’t much kinder to the new arrangements of his hits on Bob Dylan at Budokan, but his studio album released the same summer, Street-Legal, has aged well. “Baby, Stop Crying” and “True Love Tends to Forget” feature some of Dylan’s best interplay with the team of backing vocalists that would become a recurring feature of his next few albums.

15. New Morning (1970)

New Morning arrived four months after Self Portrait with a warm, inviting sound and a set of catchy new songs that suggested that Dylan was, at least for the time being, done antagonizing and confusing his fans. Heavy on pianos and organs played by Al Kooper and Dylan himself, New Morning features a raggedly charming vocal style, somewhere between the Nashville Skyline croon and the holler Dylan would develop in the mid-’70s. The Side 2 gem “The Man in Me” went relatively unheralded until the Coen brothers used it to great effect in The Big Lebowski.

14. Modern Times (2006)

By 2006, Bob Dylan had settled into his late career renaissance, and would only descend from the mountaintop with new songs every few years. Sometimes he’d return with something odd and unexpected, like the Modern Times opener “Thunder on the Mountain” and its tangent about a young R&B star: “I was thinking ’bout Alicia Keys, couldn’t keep from crying.” The album was a hit, though, in fact the first time in 30 years that Dylan reached No. 1 on the Billboard 200. “Beyond the Horizon” is a lovely original song that resembles the pop standards that Dylan would spend most of the 2010s covering.

13. The Times They Are a-Changin’ (1964)

If there was a moment where Dylan truly became the successor to Woody Guthrie before moving on to different, less easily identifiable objectives, it was on the title track to The Times They Are a-Changin’. The stark, topical songs on Dylan’s third album include the masterpiece “The Lonesome Death of Hattie Carroll,” written after Dylan read a 1963 newspaper story about Carroll, a Baltimore barmaid who was killed by a drunken customer. “Boots of Spanish Leather,” however, is a strikingly beautiful love song that shows a side of Dylan that would be revealed more and more over the next decade.

12. Oh Mercy (1989)

Dylan and Neil Young both spent much of the ’80s in the commercial wilderness before ending the decade on an upswing with successful 1989 albums. They both did it in part with more topical message-driven records, although “Political World” isn’t quite as rousing as “Rockin’ in the Free World.” Bono introduced Dylan to Daniel Lanois, a master of atmosphere and texture who’d worked on U2’s albums, and Lanois proved to be a great producer for Dylan ballads like “Most of the Time” and “Where Teardrops Fall.”

11. Tempest (2012)

Tempest, which was recorded with an ensemble including Los Lobos guitarist David Hidalgo gathered around an omnidirectional Neumann microphone, is one of Dylan’s best-sounding late-period albums. Uptempo songs like “Pay in Blood” and “Duquesne Whistle” crackle with the energy of a band playing together in a room more than just about anything he’s released since The Basement Tapes. The lyrics brim over with characters, narratives, and vividly rendered American scenery.

10. Planet Waves (1974)

The Band became Dylan’s most-famed backing musicians after touring with him in the mid-’60s and recording a series of hit albums of their own, sometimes featuring songs they’d written with Dylan. An album of Dylan with the entire lineup of the Band didn’t hit stores until 1974, though, when they reunited for Dylan’s first (and, as it would turn out, only) album for Asylum Records. Planet Waves doesn’t entirely live up to the lofty expectations placed on this belated union, but there are numerous moments of great musical chemistry, from Robbie Robertson’s inspired lead guitar on “Going, Going, Gone” to Garth Hudson’s organ on “Something There Is About You.”

9. Time Out of Mind (1997)

After reaching a nadir on Under the Red Sky, Dylan refrained from releasing an album of new songs for seven years, an unprecedented pause in his prolific career. And in that jump from 49 to 56, Dylan had finally become the “old” man (albeit middle-aged) he’d always wanted to be on sublimely raspy, weathered songs like “Standing in the Doorway” and “Tryin’ to Get to Heaven.” The album reunited Dylan with producer Daniel Lanois, who gave the album an even more fully realized haze of reverb and distortion than he’d achieved on Oh Mercy. Time Out of Mind won the Grammy for Album of the Year, incredibly the first Dylan solo album to even be nominated for the category (Dylan also appeared on George Harrison’s The Concert for Bangladesh, which won the award in 1973). “The Bob Dylan revealed on Time Out of Mind is a man out of time, in self-imposed exile from rock trends, and all the wiser and stronger for keeping his distance from their energy-sapping fickleness,” Ken Tucker wrote in the Entertainment Weekly review of the album. 

8. Another Side of Bob Dylan (1964)

Much as Beatles for Sale was the first album the Fab Four made under the influence of Dylan, Another Side of Bob Dylan was the first album he made under the influence of the Beatles. It was also his last time, for a while, making an album with no backing musicians, but folk purists were already becoming uncomfortable with his more personal songwriting replacing protest songs. With “It Ain’t Me, Babe,” “All I Really Want to Do,” and “My Back Pages,” though, he still had a lot to say about the human condition.

7. The Basement Tapes (1975)

Dylan’s 1966 motorcycle crash is a singular event shrouded in mystery and mythology. We don’t know exactly what happened, or even if it did happen, but it began a lengthy period when Dylan rarely appeared in public and didn’t tour for years. Living in Woodstock, New York, Dylan spent a lot of time in nearby Saugerties at the Band’s famous Big Pink house, recording dozens of songs that were heavily bootlegged and sometimes sent to other artists to record. By the time The Basement Tapes was finally released nearly a decade later, songs like “Million Dollar Bash” and “Too Much of Nothing” were already legendary, and the recordings were less an album than overdue-but-valuable documentation of a potent period in Dylan’s creative life that had already passed.

6. John Wesley Harding (1967)

While Dylan’s basement recordings with the Band took years to trickle out to the public, a completely different set of songs with different players that Dylan recorded during the same period became his first post-motorcycle crash statement. John Wesley Harding featured Dylan playing acoustic with a two-man rhythm section, pulling back from the maximalism of Blonde on Blonde. Some of Dylan’s rock fanbase didn’t know what to make of the album, but one rock star, Jimi Hendrix, received an advance copy and loved it immediately. After learning multiple songs on the album, Hendrix decided to release his own version of “All Along the Watchtower,” perhaps the most transcendent Dylan cover ever recorded. It’s also Dylan’s most-performed song, and his renditions are usually heavily inspired by Hendrix’s interpretation.

5. Bringing It All Back Home (1965)

For all the controversy that Dylan encountered in “going electric,” he attempted to make a gradual transition, with Bringing It All Back Home featuring one side of full band songs and one side of solo acoustic songs. “Mr. Tambourine Man,” a holdover from the Another Side of Bob Dylan sessions, exists on the same album as “Subterranean Homesick Blues” and “Maggie’s Farm.” It’s a fascinating pivot point, Dylan operating at the top of his game in two completely different styles.

4. Highway 61 Revisited (1965)

“Like a Rolling Stone” peaked at No. 2 on the Billboard Hot 100 and, “We Are the World” notwithstanding, it represents Dylan’s pinnacle as a popular phenomenon, one of the few 6-minute hit singles of the era. Highway 61 Revisited closes with a song that’s really too long for radio, the 1-minute epic “Desolation Row.” And in between those two towering achievements, Dylan assumes the mantle of rock stardom, delivering surrealist lyrics with an iconic sneer.

3. Blood on the Tracks (1975)

Bob and Sara Dylan’s decade-long marriage was beginning to deteriorate in the mid-’70s, and from that period he produced the most emotionally resonant set of songs of his career, including “Tangled Up in Blue” and “Shelter from the Storm.” After recording a complete album in New York, Dylan re-recorded half the tracks in Minneapolis with a different set of musicians just three weeks before the release, somehow achieving a cohesive and engrossing album out of that patchwork of perfect takes. “Its loveliness is almost literally haunting, an aural déjà vu. There are moments of anger that seem callow, and the prevailing theme of interrupted love recalls adolescent woes, but on the whole this is the man’s most mature and assured record,” Robert Christgau wrote in the Village Voice review of Blood on the Tracks.

2. The Freewheelin’ Bob Dylan (1963)

The Freewheelin’ Bob Dylan is the big bang that makes everything Dylan has done since then possible, with such epochal masterpieces as “Blowin’ in the Wind,” “A Hard Rain’s a-Gonna Fall,” “Masters of War,” and “Don’t Think Twice, It’s Alright.” It makes sense that more palatable versions of Dylan’s songs by the likes of the Byrds and Peter, Paul and Mary would pave the way for the mainstream embrace of Dylan, but the sheer magnetism of his performances on Freewheelin’ truly bridged the gap between folk music and pop music. 

1. Blonde on Blonde (1966)

Even if Blonde on Blonde wasn’t the first double LP ever packaged as a single album, it made Dylan essentially the first major rock act to release more than 70 minutes of new songs at once, throwing down the gauntlet for most of his peers to release ambitious double albums in the years ahead. From the comical opener “Rainy Day Women #12 & 35” to the Side 4 epic “Sad-Eyed Lady of the Lowlands,” Blonde on Blonde simply spills forth with iconoclastic moments from Dylan at his most confident and self-possessed. Even with more and more backing musicians crowding the tracks, his words seem to punch through the songs more forcefully and meaningfully than ever on songs like “Stuck Inside of Mobile with the Memphis Blues Again.” With or without the motorcycle crash that followed a month after the album’s release, Blonde or Blonde would almost certainly represent a mountaintop that Dylan could only scale once, and never return to.  

To see our running list of the top 100 greatest rock stars of all time, click here.