Bob Dylan’s 20 greatest albums, from Blood on the Tracks to Rough and Rowdy Ways

Bob Dylan, the rock era’s greatest and most influential poet, celebrates his 80th birthday on 24 May. It is also 60 years since Dylan recorded his debut album and began a career that has embraced just about every form of popular music. His folk beginnings including his short but seismic protest era and single-mindedness in pursuing a more rock-based sound, which turned Dylan into a cultural icon of the Sixties.

In the ensuing decades, he has constantly sought to stretch the boundaries of his music, resulting in a magnificent body of work – the importance and influence of which can never be understated. Written off many times, Dylan constantly surprises, as last year’s superb Rough and Rowdy Ways album demonstrates. It’s a tantalising thought that even at 80, he may still have great work left in him.

To celebrate his milestone birthday, here is my countdown of Bob Dylan’s 20 greatest albums.

20) Planet Waves (1974)

Reunited with The Band both on tour and in the studio, Planet Waves presented a reinvigorated Dylan returning to a more rock-based sound after several years of experimentation. Planet Waves isn’t classic Dylan but when it’s good, it’s very good indeed. “Wedding Song” and “Dirge” prefigure the soul-baring intensity of Blood on the Tracks and of the two versions of “Forever Young”, stick with the heart-stirring “slow” one.

19) Slow Train Coming (1979)

Dylan’s conversion to Christianity caused almost as much furore as his electronic revolution in the mid 1960s. His God on Slow Train Coming seems a particularly merciless and vengeful one, but if it’s a hard record to like, the musicianship, production, and Dylan’s song-craft are admirable. “Gotta Serve Somebody” and “Slow Train” sum up the evangelical dogma of the album, but the mood is lightened by the beautiful ballad “Precious Angel” and the nursery rhyme simplicity of “Man Gave Names to All the Animals”.

18) Bob Dylan (1962)

Dylan’s debut album contained just two originals and the 20-year-old was clearly in thrall to Woody Guthrie, nevertheless, it was a startling introduction to his nascent talent. Authentic readings of the traditional “House of the Risin’ Sun” and “Man of Constant Sorrow” are the highlights, while “A Song for Woody” was a fitting tribute to his hero.

17) Rough and Rowdy Ways (2020)

It seems wholly appropriate that the rock era’s foremost social commentator should release an album that sound-tracked such turbulent times. Dylan’s 39th studio album was a triumph and garnered universal acclaim. “Murder Most Foul”, a 17-minute dissertation on JFK’s assassination, loaded with references to the wider 20th century cultural landscape, is destined to become as talked-about and as lionised as anything from his remarkable back catalogue.

16) Oh Mercy (1989)

Energised by his success with The Traveling Wilburys and the beginning of his Never Ending Tour, Dylan’s long period of writer’s block was alleviated when he hooked up with producer Daniel Lanois for the best record of his most barren decade. Magnificent songs such as “What Good Am I”, “Shooting Star”, “Most of the Time” and “Ring Them Bells” demonstrated that Dylan’s songwriting smarts had returned with a vengeance.

15) Another Side of Bob Dylan (1964)

There was room for one more deathless socially-conscious classic (“Chimes of Freedom”), but Dylan’s most personal album to that point was where he bade farewell to the hated “spokesman of a generation” label. “All I Really Want To Do” and “It Ain’t Me Babe” were inspired by his break-up with Suze Rotolo, and “My Back Pages” drew a veil on Dylan’s past and anticipated his next move with one of his greatest couplets: “Ah but I was so much older then/I’m younger than that now”.

14) Modern Times (2006)

Modern Times perfectly bookended Dylan’s autumnal renaissance that began with 1997’s Time out of Mind. As on 2001’s Love and Theft, Dylan immersed himself in American roots music and produced his own unique take on the music that had always inspired him. He drew some controversy for not crediting original artists, but he had borrowed tunes as far back as 1963’s “The Girl from the North Country”. Plus ça change.

13) Desire (1975)

Desire remains a prime example of Dylan’s unrivalled skill as a storyteller. Opener, “Hurricane”, about a wrongly imprisoned boxer, may not be totally factually accurate but masterfully recalls the previous decade’s classic social injustice songs. “Isis” is a rambling, surrealist widescreen epic, and “Sara” his last stab at a reconciliation with his wife whom he had savaged on Blood on the Tracks. Violinist Scarlet Rivera adds immeasurably to the overall sound and that’s a luminous Emmylou Harris you hear on backing vocals.

12) Nashville Skyline (1968)

Dylan confounded fans and critics alike as he embraced country music on a homely, deeply personal collection reflecting his domestic contentment and his love as a teenager for Hank Williams. And what’s more, his voice was now a warm, honeyed croon. “Lay Lady Lay” is the obvious standout, with the rueful “Tonight I’ll Be Staying Here with You” – one of his loveliest songs – not far behind.

11) Love and Theft (2001)

Cherry-picking from the entire lineage of American music, Dylan fashioned an album underpinned by the blues. Yet it’s also wonderfully eclectic, and most of all, fun. The rockabilly of “Summer Days”, the delta blues tribute of “High Water (For Charlie Patton)”, the creaky beauty of “Mississippi”... Dylan hadn’t sounded so energised in years. Two decades on, Love and Theft stands as his best album of the 21st century.

10) The Times They Are a-Changin’ (1964)

By his third album Dylan’s songwriting craft was developing apace, culminating in the archetypal civil rights era protest album. The anthemic title track, “The Lonesome Death of Hattie Carroll”, “With God on Our Side” and “Only a Pawn in Their Game” rank among his most powerful statements, offering compassion, political insight, empathy and anger. However, Dylan was already looking to expand his horizons with “One Too Many Mornings”, a sad, reflective love song.

9) John Wesley Harding (1967)

A post-motorcycle accident Dylan rejected the lysergic trends of the time and produced an understated, rootsy album that anticipated the Americana genre of later decades. Peopled with hobos, drifters and various misfits, this affectionate almost spiritual celebration of the poor and the oppressed is now viewed as one of Dylan’s most significant and influential works. “All Along the Watchtower”, “Drifter’s Escape” and the mellow, countrified “I’ll Be Your Baby Tonight” are particular standouts.

8) The Basement Tapes (1975)

Recorded with The Band in Woodstock’s famed Big Pink house in 1967 after Dylan’s infamous motorcycle accident, for years these recordings represented one of the rock’s most sought after bootlegs. Finally emerging eight years later and including masterpieces such as “Tears of Rage” and “This Wheel’s On Fire” amid a grab bag of traditional American music influences, The Basement Tapes fully justified its reputation as a roots rock milestone .

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7) Time Out of Mind (1997)

Eerily prescient given Dylan’s close brush with death shortly after its release, this mighty creative rebirth is a dark dissertation on mortality and a reflection on times past. Time Out of Mind is again distinguished by Daniel Lanois’ atmospherically muddy production, but it is the emotional impact of the songs and Dylan’s fragile voice that matter most. “Love Sick” and 16-minute epic “Highlands” are fantastic, but “Not Dark Yet” is the key song, one of Dylan’s greatest and most insightful ever.

6) The Freewheelin’ Bob Dylan (1963)

A year in the making, and a quantum leap from his debut, Dylan’s first classic album marked his coming of age as a composer. With the Cuban missile crisis fresh in the memory, Dylan captured the zeitgeist perfectly with timeless protest songs “Masters of War”, “Blowin’ in the Wind” and “A Hard Rain’s a-Gonna Fall”. And the achingly beautiful “Girl from the North Country” and “Don’t Think Twice, It’s Alright” surely rank near the top of any list of Dylan’s greatest love songs.

5) The Bootleg Series Vol. 4: Bob Dylan Live 1966, The “Royal Albert Hall” Concert (1966)

The in-joke title alludes to the infamous “Judas” cry erroneously attributed to Dylan’s London gig of his infamous and pivotal “electric” revolution. Manchester Free Trade Hall was of course the venue for this recording with The Hawks, soon to become The Band. Now however, the most striking aspect of one of the most iconic cultural events of the 1960s isn’t so much the impact of the plugged-in music, as Dylan’s venomous delivery.

4) Bringing It All Back Home (1965)

A new genre, folk-rock, was born with this touchstone album split into two halves, one electric, one acoustic. The two-minute twenty seconds adrenaline rush of “Subterranean Homesick Blues” kicks off the electric side and it’s a hard act to follow. However, side two’s four acoustic songs – including “Mr Tambourine Man” and “It’s All Over Now, Baby Blue” – represent one of the greatest runs of classic Dylan songs.

3) Highway 61 Revisited (1965)

A landmark recording in the history of rock – a completely new type of music brimming with surrealist poetry against a backdrop of a swirling, hypnotic amalgam of folk, blues and swing powered by Al Kooper’s organ and Mike Bloomfield’s blues guitar. Infinitely influential with game-changing songs such as “Ballad of a Thin Man”, “Tombstone Blues”, “Desolation Row”, and of course, “Like a Rolling Stone” which, even if it isn’t the greatest rock ‘n’ roll record ever, I have yet to hear a better one.

2) Blood on the Tracks (1974)

Dylan’s raging cri de cœur over the disintegration of his marriage is a masterpiece of such soul-bearing intensity that Dylan himself said that he couldn’t understand why people would want to listen to it. The vitriol of “Idiot Wind”; the dazzling wordplay of “Tangled Up in Blue”; the heartache of “You’re a Big Girl Now” and “If You See Her, Say Hello”; the narrative drive of “Lily, Rosemary and the Jack of Hearts” and a life-affirming “Simple Twist of Fate” emphatically reasserted Dylan’s genius on an album that, once heard, is never forgotten.

1) Blonde on Blonde (1966)

Released just weeks before his infamous motorcycle crash during that tumultuous, epochal year for Dylan and rock music, Blonde on Blonde found Dylan at his most expansive and productive. With an unbelievably high concentration of classic songs on the record’s four sides, the record includes “Just Like a Woman”, “I Want You”, “One of Us Must Know”, and the masterful, sprawling ballads “Visions of Johanna” and “Sad Eyed Lady of the Lowlands”. Blonde on Blonde bookended Dylan’s first classic period and its reputation as the artist’s magnum opus endures. One of the greatest albums ever made.