While some will prefer Dylan’s earlier, more stripped-back folk records, there are others who will assert that he peaked later in the 1960s as he embraced a more surreal, stream-of-consciousness style of writing. There’s an argument that Dylan was at his poetic best in the 1970s, although some will swear by the older, Dylan’s music represent one of the greatest bodies of work by any artist who ever lived.

10 Oh Mercy (1989)

Bob Dylan had a major career comeback with his 26th studio album

After a string of poorly received records throughout the 1980s, many longtime listeners had started losing faith in Bob Dylan before the release of Oh Mercy in 1989. However, Dylan had a major comeback with Oh Mercy, a record that saw him team up with music producer Daniel Lanois for the first time. This album avoided the lackluster, overly 1980s production of Empire Burlesque and the underwhelming offerings of Down in the Groove and was replaced by an exciting return to form that proved Dylan still had something urgent to say.

Related

10 Bob Dylan Movies To Watch Before A Complete Unknown

Across documentaries, feature films, and experimental releases, there are plenty of great Bob Dylan movies to check out before A Complete Unknown.

Posts

With the opening track “Political World,” Dylan echoed the ion for protest music that had made him famous in the first place and hinted at the introspective sentimentality of his earliest days with the romantic reminiscences of “Most of the Time.” It seemed Dylan had been reinvigorated creatively from his time making the Traveling Wilburys supergroup debut album the year before, and that ion carried over into this record. Oh Mercy was the first of several late-career triumphs for Dylan that showcased to audiences that he always found a way to get out of any creative rut.

9 John Wesley Harding (1967)

Bob Dylan got back to his folk roots with his eighth studio album

Recorded around the same time as The Basement Tapes, his astounding home sessions record with The Band, John Wesley Harding was a return to a more acoustic and folk-influenced style after the rock n’ roll excesses of Bob Dylan’s previous few albums. With lyrics that were grounded in realism and evocative imagery, the surreal stream-of-consciousness style of Blonde on Blonde was replaced with more streamlined poetic writings on John Wesley Harding. Recorded after Dylan retreated to Woodstock following his 1966 motorcycle accident, this record was Dylan getting back-to-basics and finding a new creative voice in the process.

While to the average music fan the highlight of John Wesley Harding will be "All Along the Watchtower,” a song made even more famous through Jimi Hendrix’s cover, the entire record was full of incredible Dylan musings. Tracks like “The Ballad of Frankie Lee and Judas Priest” act as parables on finding meaning and purpose through one's existence, and it's clear this record was Dylan in a more introspective mood than the drug-infused wildness of his previous years.

8 The Times They Are A-Changin' (1964)

Bob Dylan fully embraced protest music on his third studio album

Although many think of Bob Dylan as primarily a protest singer, this was actually just a very brief period of his career that was best encapsulated by The Times They Are a-Changin’. This 1964 record featured pointed political anthems on issues of racism, poverty, and social change, which led to Dylan being characterized as the voice of his generation for his ability to capture the progressive beliefs of youth culture in the 1960s. From its powerful opening title track, The Times They Are a-Changin’ immediately became a timeless declaration on the need for change.

Other songs like “With God on Our Side” and "The Lonesome Death of Hattie Carroll" revealed Dylan’s unmatched skills for capturing society's hypocrisies and ills into brief folk songs that transcend generations. While The Times They Are a-Changin’ was Dylan’s most outright political record up to this point, it still contained hints at the introspective romantic seen in The Freewheelin’ Bob Dylan with the song “Boots of Spanish Leather.” With richly layered character dynamics and raw vulnerability, songs like this were an early indication of Dylan’s future status as a Nobel Prize winner.

7 Rough And Rowdy Ways (2020)

Bob Dylan proved he’s sharp as ever with his 39th studio album

It’s a testament to Bob Dylan’s unmatched legacy that an album of new material still felt like a major musical event in 2020 when he surprised everyone with the release of one of his best albums, Rough and Rowdy Ways. Things kicked off with the surprise release of “Murder Most Foul,” a sprawling near-17-minute song that captured the modern history of the United States through the lens of the assassination of John F. Kennedy. With razor-sharp lyricism and plenty of wit, there was a real ethereal beauty in the song that was then accompanied by an equally astounding album.

It’s hard to know whether Rough and Rowdy Ways will be Dylan’s final album of new material, but if that were the case, he’d have bookended his career on a high note. Tracks like "I Contain Multitudes" and “False Prophet” seemed to lean into Dylan’s life and legacy, as his rugged, older, bluesy style of singing lent itself well to the record. Rough and Rowdy Ways felt like an old legend playing to an eager, intimate crowd in a small, smoke-filled bar as Dylan proved once again that he's never lost it.

6 Time Out Of Mind (1997)

Bob Dylan looked mortality in the eye with his 30th studio album

There was a sense that Bob Dylan was coming to the end of the line on Time Out of Mind, the first of many records that fans interpreted as a final farewell. With a haunting atmosphere and dark lyrics that addressed mortality head-on, it felt like Dylan had found a new musical voice with Time Out of Mind. Dylan sounded older and wiser on this record as he grappled with death on songs like "Tryin' to Get to Heaven" and "Not Dark Yet,” two tracks that were as profound as anything he’d written in the 1960s.

Time Out of Mind also had a commercial appeal, as his oft-covered love song "Make You Feel My Love" has become a modern standard that will be well known to many non-Dylan fans through Adele’s beloved rendition. Time Out of Mind concluded with the excellent “Highlands,” a 16-minute epic that transported listeners to another world. As Dylan’s reunion with the Oh Mercy producer Daniel Lanois, Time Out of Mind was his last album before he started to self-produce all of his records.

5 The Freewheelin’ Bob Dylan (1963)

Bob Dylan truly found his voice on his second studio album

Although Bob Dylan released his self-titled debut in 1962, it wasn’t until the following year that the true extent of his talent was on display with the release of The Freewheelin’ Bob Dylan. While Dylan’s first record had hints of songwriting skills with the self-penned track “Song to Woody,” on Freewheelin’, Dylan wrote practically every song, and the world was introduced to a true songwriting legend. As a record that is still emulated by countless singer-songwriters to this day, Freewheelin’ laid the groundwork for modern indie folk and was the bible for every nasally-singing Bob Dylan wannabe with an acoustic guitar.

From its opening track, "Blowin’ in the Wind,” which summed up Dylan’s reputation as the voice of his generation in under three minutes, to the poetic vulnerability of "Don't Think Twice, It's All Right,” at just 21 years old it was clear that this was a writer wise beyond his years. Tracks like "Masters of War" and "A Hard Rain's a-Gonna Fall" laid the groundwork for Dylan’s more protest-oriented follow-up record. Freewheelin’ had aspects of everything that made Dylan great in the 1960s, and from this point on he became the benchmark by which all other folk acts judged themselves.

4 Bringing It All Back Home (1965)

Bob Dylan shocked the folk scene by going electric on his fifth studio album

The release of Bringing It All Back Home was a major moment in music history as Bob Dylan traversed genres and alienated countless people along the way. As a record that’s split into two distinct halves, the first side featured Dylan going all out on fast-paced electric songs, signaling the dawning of a new rock n’ roll star, while side two harkened back to his roots with more folk, acoustic-oriented music. Bringing It All Back Home also abandoned protest music in favor of more surreal and cryptic poetic lyricism.

Kicking off with "Subterranean Homesick Blues,” this album was the dawning of the sunglass-wearing, cigarette-smoking, speed freak Dylan as he carved out an entirely new persona for himself. There’s an anti-establishment punk rock energy to songs like "Maggie's Farm" while also delivering complex lyrical masterpieces such as "It's Alright, Ma (I'm Only Bleeding).” Bringing It All Back Home proved that Dylan could rock out with the best of them and that he was capable of branching out well beyond his folk music and traditional roots.

3 Blonde On Blonde (1966)

Bob Dylan leaned fully into a surreal, stream-of-consciousness style on his seventh studio album

The sheer volume of output from Bob Dylan during the mid-1960s was astounding, with his non-stop songwriting culminating in the epic double album Blonde on Blonde. This record leaned into the surreal, stream-of-consciousness style that Dylan had been developing since Bringing It All Back Home and, along with Highway 61 Revisited, completed a trilogy of records that was unmatched by any other artist, bar arguably the Beatles. As a complex and cryptic postmodern record, Blonde on Blonde captured the essence of Dylan’s surreal era before things became more stripped back and grounded with John Wesley Harding the following year.

Things kicked off with the hilarious "Rainy Day Women #12 & 35,” whose repeated chorus of “Everybody must get stoned” highlighted Dylan’s playful nature. However, this sprawling record also included incredible love songs like "I Want You" and "Just Like a Woman" that showcased a poet at the top of his game. Although none of this compares to the final track, "Sad Eyed Lady of the Lowlands,” a song filled with literary allusions whose impenetrable nature was almost Joycean in its unknowable but powerfully beautiful appeal.

2 Highway 61 Revisited (1965)

Bob Dylan broke new ground with his sixth studio album

Any album that kicks off with "Like a Rolling Stone" was always going to rank high, but Bob Dylan somehow managed to keep that same level of quality throughout Highway 61 Revisited. This is the perfect Dylan record to explain to people why this folk artist was revered and to tap into the reason that, even today, people remain fascinated and enthralled by his music. Not only are all the songs on Highway 61 Revisited astounding examples of an artist at the top of his game, but they are filled with complexity, philosophy, and wit.

Dylan addresses his frustrations with the media’s attempts to pigeonhole him in "Ballad of a Thin Man," whose title character leaned into the preposterous nature of hapless journalists. The religious imagery found on the record’s title track even showcases that Dylan had a tendency to mine Biblical imagery for material well before he became born again in the late 1970s. Highway 61 Revisited was a perfect record and truly encapsulated the essence of Dylan’s world-conquering appeal in the 1960s.

1 Blood On The Tracks (1975)

Bob Dylan laid his soul bare on his 15th studio album

Bob Dylan’s personal life was in shambles in 1975 as his marriage was deteriorating, and he had found himself in a creative slump the previous years, yet he somehow managed to take these difficulties and put them into what was arguably his greatest achievement. Blood on the Tracks was a highly confessional and vulnerable record from Dylan that many have described as the greatest breakup album of all time. Dylan’s estrangement from his then-wife Sara informed the poetic characterization of Blood on the Tracks, which felt more like a collection of beautifully constructed short stories than a typical album.

While Dylan was rarely forthcoming about his personal life and denied Blood on the Tracks was autobiographical, he also said of the opening track, "Tangled Up in Blue," that it took “ten years to live and two years to write” (via Time.) Blood on the Tracks was Dylan’s most mature album up to that point, and it played out like a man who had nothing to prove and who wanted to lay his soul bare for the world to see. There’s a timeless beauty in Blood on the Tracks that reveals itself anew to listeners at each point in their lives.

Source: Time