Bob Dylan at 80: 10 Albums for Millennials Getting to Know Him

Bob Dylan at 80 is almost as old as Rock N’ Roll. Beginning in the early 1960s all the way to his last year’s hit album Rough And Rowdy Ways, he has had one of the most distinguished careers in the history of modern music. 

Dylan’s discography is rich — over 39 studio albums, many bootleg recordings, and numerous independent songs. For his die-hard fans, both old and young, he’s been the ultimate songwriter, with songs like “Blowin’ In The Wind,” “Masters Of War,” “A Hard Rain’s A-Gonna Fall,” “The Times They Are A-Changin,” “Like A Rolling Stone” and “Positively 4th Street” being relevant or impactful even today. Though the announcement evoked mixed reactions, the fact that he won the Nobel Prize for Literature in 2016 speaks volumes about his range and influence.

Born Robert Allen Zimmerman on May 24th, 1941, to a Jewish family in Duluth, Minnesota, Dylan grew up on rock n’ roll acts like Little Richard and Elvis Presley, but later took to the folk music of Woody Guthrie and Pete Seeger. He began as a folk singer, and took the name Bob Dylan as a nod to his favorite poet Dylan Thomas. His self-titled 1962 debut album consisted of familiar folk, blues and gospel songs, besides two originals.

His second album The Freewheelin’ Bob Dylan was hugely successful, and “Blowin In The Wind” became an anthem with its lines “How many deaths will it takes till he knows, that too many people have died?” While his earlier albums blended folk-style tunes with protest lyrics, he later added rock elements to create a distinct folk-rock sound. Not everybody accepted the change, and he was booed at the 1965 Newport Folk Festival for going electric.

Dylan’s voice and singing style have always been subjects of debate. Some felt he was too nasal and even irritating, whereas others acquired the taste, describing his voice as unique and complementary to his lyrics, and the harmonica that often accompanied his songs. With time, his words moved from the protest emphasis, as he populated his songs with characters and descriptions of events, besides surreal references. He had a religious phase in the late 1970s, after converting to Christianity. He has been the subject of numerous academic research work, the most famous of which is Do You, Mr. Jones? a collection of essays on Dylan by academics edited by Neil Corcoran, Emeritus Professor of English at the University of Liverpool. 

Like many long-standing musicians, Dylan had his ups and downs, with many 1980s albums lacking the earlier class. He made a comeback of sorts in 1997 with Time Out Of Mind, where one first noticed that his voice was smokier and gruffy, the instrumentation was more atmospheric and the lyrics was more like lengthy poetry.

For those who have just discovered Dylan here is a list of 10 albums that capture his style and musical evolution. While one could always pick a greatest hits compilation, the advantage of individual albums is that they represent a similar period and style. This is neither a list of the writer’s personal favorites nor is it based on commercial performance. To choose only 10 out of 39 is a tough task, but these 10 broadly represent Dylan’s oeuvre. In keeping with the evolution of Dylan’s career, the order is chronological.

The Freewheelin’ Bob Dylan (1963)

His second album paved the way for Dylan’s sudden popularity. Besides the anthem “Blowin’ In The Wind,” it had the classic “A Hard Rain’s A-Gonna Fall,” which was filled with symbolist imagery and inspired by the French poet Arthur Rimbaud. The anti-Cold War song “Masters Of War” and the simple “Don’t Think Twice, It’s All Right” also adorned this set. Old-time fans insisted that lyrically, this was one of Dylan’s most intense albums.

Bringing It All Back Home (1965)

A mix of electric and acoustic songs, this album marked the turning point in Dylan’s sound. “Subterranean Homesick Blues” represented a different side of Dylan’s singing, fast and breezy, with the line, “You don’t need a weatherman to know which way the wind blows.” It also had “She Belongs To Me” and “It’s All Over Now, Baby Blue,” which had opposite emotions. These were besides the imagery-filled “Mr. Tambourine Man.”

Highway 61 Revisited (1965)

Released just five months after Bringing It All Back Home, Highway 61 Revisited completed Dylan’s transition from folk star to rock star. One of his biggest hits, the cynical “Like A Rolling Stone” opened the album, and the lines, “How does it feel, aah how does it feel, to be on your own, with no direction home, like a complete unknown, like a rolling stone?” struck a chord. Other popular cuts were “Ballad Of A Thin Man” and the 11-minute “Desolation Row.”

Blonde On Blonde (1966)

Around this time, Dylan had become so prolific that barely 10 months after releasing Highway 61 Revisited, he released the double album Blonde On Blonde. The songs “Visions Of Johanna,” “Sad-Eyed Lady Of The Lowlands” and “One Of Us Must Know” were considered high points of his writing, with the last one containing the lines, “But, sooner or later, one of us must know, that you just did what you’re supposed to do; Sooner or later, one of us must know, that I really did try to get close to you.”

Blood On The Tracks (1975)

Despite some great songs, Dylan’s albums had become erratic by the end of the 1960s. Blood On The Tracks marked a return to form, and was more personal than many other albums, as he wrote it when he was having differences with his wife Sara. Stand-out songs were “Tangled Up In Blue,” “Shelter From The Storm,” “Idiot Wind” and “Simple Twist Of Fate,” which was about a romantic relationship that didn’t work out. 

Desire (1976)

In many ways, Desire was the best example of Dylan’s versatility. On “Hurricane,” he wrote about boxer Rubin Carter, and on “Joey,” about the gangster Joey Gallo. “Romance in Durango” was about an outlaw’s love affair and “Black Diamond Bay” talked of a natural disaster. “Isis” used ancient Egypt as a metaphor, and “Sara” was considered his most personal song ever. “Sara, Sara, so easy to look at, so hard to define,” he sang.

Infidels (1983)

In the late 1970s, began a Christian album trilogy. Infidels came after that, and despite Biblical references in the opening song “Jokerman,” the album had a mix of political and personal songs. “Union Sundown” was a statement against imported consumer goods, and “Man Of Peace” was about evil. “Don’t Fall Apart On Me Tonight” was a love song, and “Sweetheart Like You” asked, “But what’s a sweetheart like you doing in a dump like this?” Mark Knopfler of Dire Straits co-produced the album and played guitar.

Time Out Of Mind (1997)

For over a decade after Infidels, Dylan struggled with his musical output. The 1997 album Time Out Of Mind ended the drought, winning three Grammy awards. On “Love Sick,” the songwriter showed his earlier class, singing vicious lines like, “I’m sick of love, I wish I’d never met you, I’m sick of love, I’m tryin’ to forget you.” His voice was now gruffer, the instrumentation was more atmospheric, and he focused on lengthy poetry on “Standing In The Doorway,” “Can’t Wait,” “Not Dark Yet” and the 16-minute “Highlands.”

Tempest (2012)

Lyrically, Tempest was one of Dylan’s darkest and most vivid albums ever, filled with words and tales of gore, doom and uncertainty. Lines like “You’ve got the same eyes that your mother has, if only you could prove who your father was,” “If love is a sin then beauty is a crime, all things are beautiful in their time” and “Your father left you, your mother too; Even death has washed its hands of you” was trademark Dylan. The epic title song was based on the sinking of the Titanic, whereas “Roll On, John” was a tribute to John Lennon.

Rough And Rowdy Ways (2020)

Coming after a string of recordings from the Great American Songbook, Rough And Rowdy Ways was another archetypal Dylan record. A highlight was the 17-minute “Murder Most Foul,” the longest song he recorded. Beginning with an allusion to President Kennedy’s assassination in 1963, he paid tributes to his favorite musicians. Other masterly songs were “I Contain Multitudes,” “Goodbye Jimmy Reed,” “Key West” and “False Prophet.” This is considered a modern classic.

As mentioned earlier, this list  is only an introduction to Dylan’s career. Obviously, he has released many other great albums, including Another Side Of Bob Dylan and Love And Theft, besides his recordings with The Band and Grateful Dead, and his song “Things Have Changed” from the 2000 film Wonder Boys. He also had his share of forgettable albums.

Besides his own output, Dylan has been a huge influence on many younger songwriters,  and was perhaps matched in poetic depth by Leonard Cohen and Jethro Tull’s Ian Anderson. Despite the tweaks in his style, he remains as relevant today as he was five decades ago, and that’s something that promises to continue. Fans are already waiting for his 40th studio album, and that should be another milestone.