The 10 Biggest Songs Of Bob Dylan’s Career

The Bob Dylan biopic A Complete Unknown has led to many new listeners unsure of where to start with the singer’s vast catalog. With an over 60-year career and dozens of studio albums that traverse blues, folk, country, rock, and even gospel, whittling Dylan’s work down to just ten songs is a daunting task considering just how massive an impact he has had on social and political culture across the 20th and 21st centuries. While viewers heard plenty of great songs through Timothée Chalamet’s excellent portrayal, this was just the tip of the iceberg when it comes to Dylan.

As a protest singer, folk icon, rock innovator, and reluctant voice of his generation, Dylan has remained relevant throughout each decade of his career and always managed to come back on top throughout his many ups and downs. As perhaps the most influential singer-songwriter who ever lived, his timeless lyricism and endless innovation meant his back catalog is the benchmark by which all other poetic music writers are judged. While everyone’s opinions will differ on what his biggest songs are, each track here is essential to understanding the man, myth, and legend known as Bob Dylan.

10

“Song To Woody”

Bob Dylan (1962)

Bob Dylan has always worn his influences on his sleeve, a fact clear from his debut self-titled album from 1962. While that first album was mostly covers of folk standards, the self-penned track “Song to Woody” explored Dylan’s appreciation for the folk legend Woody Guthrie. With the passion and enthusiasm of a 20-year-old kid who had recently arrived in New York city aboard a freight train from Minnesota, this song was the first clue toward Dylan’s future status as the voice of his generation, as he paid tribute to a musical legend while opening the door to become one himself.

Woody Guthrie was one of the most important figures in American folk music, whose songs of socialism and anti-establishment beliefs, such as “This Land Is Your Land,” were great catalysts for social change. A direct link can be made to Dylan’s future status as a protest music legend and Guthrie’s trailblazing influence. While Guthrie was already in ill health by the time Dylan had made it to New York, there’s a legend depicted in A Complete Unknown that the burgeoning folk singer snuck into his idol’s hospital room and sang this song to him as he struggled with Huntington’s disease.

9

“Blowin’ In The Wind”

The Freewheelin’ Bob Dylan (1963)

The ethos of the civil rights movement can be summed up in Bob Dylan’s “Blowin’ in the Wind,” a track that poses eternal questions about peace, freedom, and war. As Dylan confronted listeners with the timeless pondering, “How many roads must a man walk down before you call him a man?” and the philosophically rich response that the answer was “blowing in the wind,” he captured in one simple phrase the drive for social change. “Blowin’ in the Wind” was an anthem that has endured through generations and been utilized as a calling card for progressive beliefs for hordes of activists.

“Blowin’ in the Wind” was the opening track of Dylan’s second album, The Freewheelin’ Bob Dylan, that also included other protest songs like “Masters of War” and “A Hard Rain’s a-Gonna Fall.” Dylan continued writing in this vein in subsequent albums on songs like “The Times They Are a-Changin'” and “The Lonesome Death of Hattie Carroll,” which similarly captured the trials and tribulations of the civil rights movement in the 1960s. While Dylan has had countless iconic songs, to the casual listener, “Blowin’ in the Wind” was perhaps his definitive track.

8

“Don’t Think Twice, It’s Alright”

The Freewheelin’ Bob Dylan (1963)

While Bob Dylan carved out his legacy in his early career as an icon of protest music, he had an equally impressive talent for composing beautifully vulnerable love songs. Tracks like “Girl from the North Country,” “Boots of Spanish Leather,” and “Love Minus Zero” showcase Dylan as an emotive writer capable of capturing complex emotions within the confines of a simple folk song. Out of all these heartfelt melodies, “Don’t Think Twice, It’s Alright” perfectly summed up the bittersweet resignation of a failed relationship coming to an end.

Dylan wrote “Don’t Think Twice, It’s Alright” around the time of his relationship with Suze Rotolo, who was renamed Sylvie Russo in the biopic A Complete Unknown. With a finger-picked acoustic style, the song has had an enduring influence on countless future indie folk artists who have mimicked Dylan’s nasally confessional style of writing and singing. There was a mature wit to “Don’t Think Twice, It’s Alright” that meant it feels simultaneously timeless and modern, as Dylan’s writing suggests a guarded sense of emotional protection as he mourns the end of a once-blossoming love affair.

7

“Subterranean Homesick Blues”

Bringing It All Back Home (1965)

Bob Dylan’s Bringing It All Back Home started with a bang as “Subterranean Homesick Blues,” not only signaled his transition into electric rock music but also his new lyrical style categorized by surreal, stream-of-consciousness imagery. As Dylan’s first single to chart in the US, by this point in 1965, the singer’s frantic, speed-addled, sunglasses-wearing persona was fully formed, and he had already achieved a kind of mythic status within pop culture. With an innovative music cue card video, this felt totally modern and acted as the perfect representation of Dylan’s controversial musical transformation that was depicted in A Complete Unknown.

“Subterranean Homesick Blues” was packed with literary references and allusions that distilled 1960s youth culture into two minutes and twenty seconds. While folk purists bemoaned Dylan’s decision to move past protest music, lines like “you don’t need a weatherman to know which way the wind blows” were still extremely tapped into far-left ideology, the cultural zeitgeist, and opposition to the Vietnam War. This song signaled the dawning of a new era for Dylan that had a fast-paced, anti-establishment energy that predated punk rock by more than a decade.

6

“Like A Rolling Stone”

Highway 61 Revisited (1965)

It’s a testament to the importance of Bob Dylan’s classic song “Like a Rolling Stone” that its lyrics inspired the title of A Complete Unknown as he sang: “How does it feel? To be on your own, with no direction home, a complete unknown, like a rolling stone.” This was Dylan’s first hit single and the culmination of his transition into rock n’ roll, as its electric guitar licks, organ chords, and youthful cynicism tapped the mood of its era. This track turned Dylan into a titanic figure of pop music, as his popularity was only rivaled by the Beatles.

“Like a Rolling Stone” has commonly been ranked as Dylan’s greatest composition and was listed at number one in Rolling Stone magazine’s 500 Greatest Songs of All Time in their 2004 and 2010 lists. Dylan himself acknowledged the song’s special place in his catalog and said it felt like it was given to him by a “ghost” (via Far Out) whose spirit allowed him to write it. With its signature Hammond B2 organ riff improved by the session musician Al Kooper, “Like a Rolling Stone” was a watershed moment in the history of rock music.

5

“Knockin’ On Heaven’s Door”

Pat Garrett & Billy the Kid (1973)

The late 1960s and early 1970s saw Bob Dylan embrace a more stripped-back and grounded lyrical style compared to the surreal excesses of the Blonde on Blonde era, as albums like John Wesley Harding and New Morning had a more relaxed and introspective feeling to them. This new era saw Dylan explore acting with a role in the Sam Peckinpah Western film Pat Garrett and Billy the Kid. While Dylan’s soundtrack album was mostly comprised of instrumental recordings, it also included one of his biggest songs.

“Knockin’ On Heaven’s Door” is one of Dylan’s most well-known post-1960s songs and has been famously covered by artists like Eric Clapton and Guns N’ Roses. As a worldwide hit, the simple beauty of this track directly described the film’s scene it was in as it explored mortality, resignation, and the inevitability of death. With a lasting cultural impact that far exceeds the film it was written for, “Knockin’ on Heaven’s Door” addressed universal themes of life and death in a way that has transcended its origins.

4

“Hurricane”

Desire (1976)

While Bob Dylan was criticized for moving on from protest music in the mid-1960s, he returned to his activist roots for the epic true crime story song “Hurricane.” This sprawling eight-and-a-half-minute narrative told the story of the imprisonment of boxer Rubin “Hurricane” Carter, a man Dylan asserted was wrongly convicted for a crime he didn’t commit. While “Hurricane” addressed one man’s story, Dylan used Carter’s imprisonment as a symbol for the woes of racism and criminal profiling across the United States.

Dylan did more than just write one song for Carter, as the release of “Hurricane” was followed by a benefit concert with his traveling music troupe, the Rolling Thunder Revue, at Madison Square Garden (via Rolling Stone), which raised $100,000 for his defense. As one of Dylan’s most powerful songs, “Hurricane” came just one year after the creative triumph that was the Blood on the Tracks album, which many rank as Dylan’s best record. The song raised public awareness of Carter’s campaign for release, and his conviction was finally overturned in 1985.

3

“Make You Feel My Love”

Time Out of Mind (1997)

By the 1990s, Bob Dylan had earned his status as an elder statesman of rock music, but, in many ways, he felt like a relic of a bygone era whose relevance had dwindled over the years. That was until the release of Time Out of Mind in 1997, a comeback record that showcased an older, wiser Dylan who was addressing issues of mortality head-on. While this record included fan favorites like “Highlands,” it also featured one of Dylan’s best-known and most consistently covered songs.

“Make You Feel My Love” has become something of a modern standard as it’s been covered by over 450 different artists, including Billy Joel and Adele. As a heartfelt ballad about unconditional love, the track had a genuine sentimentality that was unusually honest for the often cryptic and notoriously guarded Dylan. As a wedding favorite, the unabashed romanticism of the song has resonated across genres and generations.

2

“Things Have Changed”

Wonder Boys (Music from the Motion Picture) (2000)

From the Nobel Prize in Literature to the Presidential Medal of Freedom, the number of awards presented to Bob Dylan is practically endless, and after the release of “Things Have Changed” he could add Oscar winner to his long list of accolades. This song was written for Curtis Hanson’s comedy-drama Wonder Boys, which starred Michael Douglas as an English professor dealing with his wife leaving him and a litany of personal and professional problems. Stylistically, the track continued in the same vein as the music from Time Out of Mind and proved Dylan’s creative renewal was not just a one-off event.

With playful yet ominous lyrics that cynically reflected on life’s complexities and the passage of time, “Things Have Changed” kicked off the 21st century with Dylan as razor-sharp and evocative as ever. As the decade continued with records like “Love and Theft” and Modern Times, it was clear Dylan had found a way to maintain his creative spark as he headed toward his twilight years. While it may be true that things have changed since Dylan’s heyday in the 1960s, he has remained as relevant as ever.

1

“Murder Most Foul”

Rough and Rowdy Ways (2020)

The sudden release of “Murder Most Foul” in the midst of the pandemic came as a welcome surprise to Bob Dylan fans who hadn’t heard any albums of original material since Tempest in 2012. While Dylan released three albums of traditional pop standards in the intervening years, the epic over-16-minute song that addressed the assassination of John F. Kennedy within the wider context of American political and cultural history felt like the culmination of his entire career. By reflecting back on the political tensions of the 1960s, it felt like Dylan was reflecting on his own place within contemporary society.

“Murder Most Foul” encapsulated a new sound for Dylan that carried forward into Rough and Rowdy Ways, which also featured acclaimed singles like “I Contain Multitudes.” As a singer who has continually reinvented himself throughout his career, it’s astounding that Dylan was able to release some of his very best work just as he was about to enter his 80s. Dylan’s career has plenty of iconic songs, and the biopic A Complete Unknown only gave a brief glimpse into one short era of his career, with “Murder Most Foul” showcasing Bob Dylan may have plenty of surprises left for fans yet.

Sources: Far Out, Rolling Stone

A Complete Unknown Official Teaser Poster

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9.3/10

A Complete Unknown

BiographyDramaMusic

A Complete Unknown is a biographical movie that follows a young Bob Dylan as he integrates with New York and catches the eye of the folk singers in the area, eventually propelling him into stardom.

Release Date

December 25, 2024

Main Genre

Biography

Cast

Timothée Chalamet
, Edward Norton
, Elle Fanning
, Monica Barbaro
, Nick Offerman
, Boyd Holbrook
, P.J. Byrne
, Scoot McNairy
, Dan Fogler
, Will Harrison
, Charlie Tahan
, Jon Gennari
, Norbert Leo Butz

Character(s)

Bob Dylan
, Pete Seeger
, Sylvie Russo
, Joan Baez
, Alan Lomax
, Johnny Cash
, Harold Levanthal
, Woody Guthrie
, Albert Grossman
, Bob Neuwirth
, Al Kooper
, Stage Manager

Director

James Mangold

Writers

Jay Cocks
, James Mangold

Studio(s)

Searchlight Pictures
, The Picture Company
, Automatik Entertainment

Distributor(s)

Searchlight Pictures

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