Bob Dylan is more than just a musician—he’s a cultural icon whose music has shaped generations. With a career spanning over six decades, Dylan has consistently pushed the boundaries of songwriting, blending folk, rock, and blues with poetic lyrics that often challenge the status quo. From his early days as a protest singer in the 1960s to his later explorations of love, loss, and spirituality, Dylan’s songs have captivated listeners around the world. His ability to capture the spirit of an era, while remaining timeless, is what makes his music so enduring. Whether you’re a lifelong fan or just discovering his work, there’s no denying the influence and genius of this legendary artist. In this list, we’ll take a look at the top 10 most popular Bob Dylan songs of all time—the tracks that defined his career and left an indelible mark on music history. From anthems of social change to deeply personal ballads, these songs represent the very best of Dylan’s unparalleled legacy. Dive in and rediscover the timeless magic of one of the greatest songwriters of all time.

1. Like a Rolling Stone (1965)

Released in July 1965, “Like a Rolling Stone” wasn’t just a milestone for Bob Dylan—it redefined the boundaries of popular music. At over six minutes long, the song defied radio conventions with its length and daring subject matter. Its scathing lyrics tell the story of a person’s fall from grace, highlighted by the iconic question, “How does it feel?” The blend of electric guitar, swirling organ, and Dylan’s unpolished, impassioned voice created a sound that fused folk storytelling with the raw energy of rock. This groundbreaking track marked a turning point in Dylan’s career and mirrored the cultural upheavals of the 1960s, earning its place as one of the most celebrated songs in music history.

2. Blowin’ in the Wind (1963)

Debuting on The Freewheelin’ Bob Dylan in 1963, “Blowin’ in the Wind” quickly became a defining anthem of the civil rights movement. With its simple yet profound lyrics, Dylan poses rhetorical questions about justice, freedom, and peace, anchoring the song in universal themes. The refrain, “The answer, my friend, is blowin’ in the wind,” is a poetic call to reflection and action, suggesting that solutions are both near and elusive. Covered by numerous artists, including Peter, Paul, and Mary in a rendition that further amplified its reach, the song transcended its time to speak to generations seeking change. Its timeless message continues to inspire social movements worldwide.

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

Released as the title track of his third album in January 1964, “The Times They Are a-Changin’” is Dylan’s rallying cry for transformation. Written amid the civil rights movement, its verses urge people to embrace progress and warn those clinging to the past of inevitable upheaval. With its folk roots and anthemic lyrics, the song became a beacon for the 1960s counterculture, symbolizing the decade’s spirit of revolution. Its impact resonates far beyond its era, often quoted in political discourse and protests, solidifying its status as a timeless anthem for change.

4. Tangled Up in Blue (1975)

Opening his 1975 album Blood on the Tracks, “Tangled Up in Blue” is a masterclass in narrative songwriting. Dylan weaves a fragmented, nonlinear tale of love and heartbreak, creating an intimate yet enigmatic portrayal of relationships. The song’s emotional depth is heightened by its blend of folk-rock melodies and Dylan’s raw, melancholic delivery. As one of his most personal works, it reflects on themes of loss and self-discovery while inviting listeners to interpret its layered storylines. “Tangled Up in Blue” is widely regarded as a highlight of Dylan’s career, a testament to his unmatched ability to make the personal universal.

5. Mr. Tambourine Man (1965)

First appearing on Bringing It All Back Home in March 1965, “Mr. Tambourine Man” is a poetic odyssey into the surreal. Its vivid, dreamlike imagery and lilting melody create an almost hypnotic atmosphere, inviting listeners to explore themes of creativity, escape, and transcendence. While interpretations of the song vary widely, its enigmatic lyrics have captured imaginations for decades. The Byrds’ electrified cover later that year brought the song mainstream success, but Dylan’s acoustic original remains hauntingly beautiful, cementing its place in the folk-rock canon.

6. All Along the Watchtower (1967)

“All Along the Watchtower,” from Dylan’s 1967 album John Wesley Harding, is one of his most enigmatic works. Its cryptic lyrics, featuring characters like the joker and the thief, have inspired countless interpretations ranging from biblical allegories to social commentary. The song’s minimalist arrangement reflects Dylan’s shift toward a stripped-down sound, amplifying its haunting, mysterious tone. While Jimi Hendrix’s legendary cover in 1968 turned it into a rock classic, Dylan’s original version retains a quiet intensity that continues to captivate listeners.

7. Subterranean Homesick Blues (1965)

From 1965’s Bringing It All Back Home, “Subterranean Homesick Blues” is a frenetic burst of lyrical innovation. Often hailed as an early precursor to rap, the song features rapid-fire verses brimming with cultural and political commentary. The iconic opening line, “Johnny’s in the basement, mixing up the medicine,” sets the stage for a chaotic, rebellious critique of 1960s society. Accompanied by a groundbreaking video of Dylan flipping cue cards with the lyrics, the song embodies the countercultural energy of the era and marks a pivotal moment in his transition from folk to rock.

8. Knockin’ on Heaven’s Door (1973)

Written for the soundtrack of Pat Garrett & Billy the Kid in 1973, “Knockin’ on Heaven’s Door” is a haunting meditation on mortality. Its sparse arrangement and simple, poignant lyrics convey a profound emotional depth. With its refrain, “Knock, knock, knockin’ on heaven’s door,” Dylan captures the universal human confrontation with life’s fragility. While it was born in the context of a Western film, the song’s themes transcend genres and generations, inspiring countless covers and enduring as one of Dylan’s most iconic works.

9. Don’t Think Twice, It’s All Right (1963)

From The Freewheelin’ Bob Dylan (1963), “Don’t Think Twice, It’s All Right” is a quietly devastating farewell to a failed relationship. Blending intricate folk fingerpicking with lyrics that are both tender and biting, the song captures the bittersweet process of moving on. Dylan’s conversational delivery adds an intimacy that makes the song feel deeply personal yet universally relatable. Its understated melancholy and emotional nuance have made it one of his most enduring breakup anthems, beloved for its authenticity and timelessness.

10. A Hard Rain’s A-Gonna Fall (1963)

“A Hard Rain’s A-Gonna Fall,” from 1963’s The Freewheelin’ Bob Dylan, is a sprawling, apocalyptic ballad that confronts a world teetering on the edge. Written during the height of Cold War anxieties, the song’s vivid, often surreal imagery addresses themes of war, environmental destruction, and societal collapse. Its prophetic verses are underscored by a haunting melody that lingers in the listener’s mind. While often linked to fears of nuclear annihilation, the song’s universal message of catastrophe and hope ensures its relevance across decades and global crises. It stands as one of Dylan’s most powerful and enduring works.