20. Ballad of a Thin Man
Kevin Winter/Getty Images for AFIWith cryptic lyrics sung in a way that only Bob Dylan can, this song is laced with biting sarcasm that painted one “Mr. Jones” as tragically unhip — so much so that even the simplest cultural references go over his head. Dylan plays the piano with haunting, circus-like riffs, which adds to the song’s eerie vibe and perfectly matches the lyrics. The song was allegedly inspired by a real-life encounter with a clueless music journalist. Whether fact or fiction, it serves as a piece of poetic justice, making Mr. Jones not just the butt of the joke, but practically its whole anatomy.
19. Visions of Johanna
Val Wilmer/RedfernsWe wouldn’t doubt that there are several children out there named Johanna because of this song. “Visions of Johanna” is a wonderful piece by Bob Dylan. The song’s tale of the elusive Johanna and the more tangible but equally complex Louise paints a picture of longing and the ghostly presence of an unattainable ideal. Dylan’s delivery — half-spoken, half-sung — is as mesmerizing as the lyrics themselves, ensuring that Johanna doesn’t just linger in the mind, but almost haunts it. Whether Johanna was real or just a figment of Dylan’s lyrical mind is up for debate. What we can say for sure, however, is this song is one of his greatest.
18. Idiot Wind
George Rose/Getty ImagesThere’s something about an angrier Bob Dylan that just sounds so right. The delivery of the line “I can’t help it if I’m lucky” is one of our favorite Bob Dylan moments, and this song has plenty. “Idiot Wind” was recorded amid his marital discord, and Dylan doesn’t just sing the lyrics; he hurls them like accusations in a storm. The song is an unforgiving reflection of betrayal and miscommunication, where every character — including Dylan himself — is flawed and frayed. Plus, who could forget the trademarked Dylan harmonica, ripping its way through the song?
17. Lay Lady Lay
Val Wilmer/Redferns/Getty ImagesThis song is Bob Dylan in a surprisingly tender light. It has a distinctly mellow vibe and rhythm that practically begs you to lie down in its field of lush lyrics. This song is a far cry from Dylan’s usual harmonica-driven sounds. Instead, it offers a softer steel guitar that wraps the listener in melodic warmth. Recorded for the soundtrack of the movie Midnight Cowboy, the song didn’t make the final cut for the film, but it still found its way into the hearts of fans worldwide. Whether he’s actually singing about a bed or a metaphorical invitation to intimacy, “Lay Lady Lay” remains one of Dylan’s most compelling pieces.
16. Girl from the North Country
Charlie Steiner – Highway 67/Getty ImagesIf there were ever a song that tugged at your heartstrings, look no further than “Girl from the North Country”. Featuring a memorable duet with Johnny Cash, Bob Dylan sings a softer, melodic tone as opposed to his usual raspy and forceful delivery. Their voices blend beautifully and add further warmth to the song. Featured on Dylan’s Nashville Skyline album, this song is technically a revisit of one of Dylan’s earlier works, a tale presumably from Dylan’s past in the chilly climate of northern Minnesota.
15. Maggie’s Farm
Michael Ochs Archives/Getty ImagesHow can you go wrong with a hearty dose of rebellion with a side of folksy sarcasm? This song is a protest against the labor grind and outright refusal to conform to the soul-sucking demands of Maggie’s exploitative farm. With its catchy, upbeat rhythm, it might trick you into tapping your foot, but the lyrics carry an unmistakable punch. Dylan’s delivery transforms what could be a simple work complaint into a manifesto of personal freedom. Recorded during his transition from folk hero to rock ‘n’ roller, “Maggie’s Farm” shows Dylan at his musical best.
14. Shelter From the Storm
Kevin Winter/Getty Images for AFIThis song is like stepping into a warm, welcoming cabin in the midst of a howling storm. In this song, Dylan crafts an allegorical refuge from life’s hardships, featuring a repetitive, gentle rhythm and a calm delivery that evokes a sense of peace and security. Featured on the seminal Blood on the Tracks album, this track is often interpreted as a reflection on personal sanctuary, whether found in love or just mere survival. “Shelter from the Storm” stands out as an iconic song, offering a lyrical umbrella under which listeners can find their own shelter.
13. Don’t Think Twice It’s Alright
Vince Maggiora/San Francisco Chronicle via Getty ImagesThis is one of Bob Dylan’s most eloquently made breakup songs, carrying a suitcase packed with wisdom and — what else — a harmonica. The gentle folk melody masks the sharpness of its words with the softness of its tune. Dylan’s lyrical shrug to a love gone sour isn’t just a farewell, but a lesson in letting go with grace, albeit a tad wryly. The song’s casual, almost offhand delivery belies the depth of its message about the futility of wasted time and lost love. Featured on his album The Freewheelin’ Bob Dylan, this song has charmed and comforted many a listener since its release.
12. Desolation Row
Jeffrey R. Staab/CBS via Getty ImagesDie-hard Dylan fans might tell you this was one of his greatest-written songs. It’s a ten-minute journey through a surreal gallery of characters — from Cinderella to Einstein in Robin Hood garb — all dwelling within society’s margins. With just his acoustic guitar and his famous harmonica, Dylan crafts a song filled with biblical and cultural references, painting a scene that’s part carnival, part apocalyptic.
11. Forever Young
Kevin Mazur/WireImageIf you ever find yourself questioning why Bob Dylan won a Nobel Prize for poetry, perhaps give this song a listen. Delivered with Dylan’s iconic raspy voice that seems to perfectly smooth out just for this occasion, the song is filled with a gentle, folky strum, creating an anthem that’s as much a lullaby for a child as it is a universal anthem for the ages. Its lyrics resonate with the desire for lasting youth — not just in years, but in the spirit of endurance.
10. Highway 61 Revisited
Michael Ochs Archives/Getty ImagesThe title track of his 1965 album mixes biblical narratives with a contemporary sound, setting the stage for a surreal Americana journey. Dylan’s sharp lyrics propose outlandish scenarios — a God suggesting Abraham use Highway 61 for a sacrifice, for instance — over a backdrop of energetic blues riffs that drive the song forward like a thundering train, making you want to tap your feet. This track is one of the few where Dylan fully leans into the use of the electric guitar, a step away from his usual acoustic sounds.
9. Subterranean Homesick Blues
Sigmund Goode/Michael Ochs Archive/Getty ImagesThis song is accompanied by one of the best (and most awkward) music videos ever. It features an incredibly young Bob Dylan with a bundle of signs, each bearing a snippet of lyrics that he discards as the song progresses. Musically, the song is a frenetic burst of folk rock that seems to barely keep up with Dylan’s rapid-fire lyrics, bordering on rap. It’s a revolutionary track that not only influenced the music video format but also signaled Dylan’s shift from folk to a more rock-driven sound.
8. Knockin’ On Heavens Door
Gai Terrell/RedfernsWritten for the soundtrack of the film Pat Garrett and Billy the Kid, the track features Dylan’s reflection on mortality, wrapped in a simple melody that has captured the hearts of audiences worldwide. The song’s simplicity makes it a powerful emotional plea, emphasized by its haunting chorus. Over the years, “Knockin’ on Heaven’s Door” has been covered countless times by a diverse array of artists, including Guns N’ Roses and Eric Clapton– each bringing their own flavor while retaining the soulful core of the original.
7. A Hard Rain’s A-Gonna Fall
Brian Shuel/RedfernsBob Dylan loves the theme of the apocalypse. Written during the tense atmosphere of the Cuban Missile Crisis, this song functions to paint an anxiety-inducing scene, each verse building on the last to create a sense of impending catastrophe. Dylan’s delivery is as powerful as ever, suggesting urgent calls to action. The prophetic tone and allegorical language make “A Hard Rain’s A-Gonna Fall” a song filled with social commentary, and a call to consciousness that resonates as deeply today as it did at the height of Cold War anxieties.
6. All Along the Watchtower
Lester Cohen/Getty ImagesA song made famous by the Jimi Hendrix cover. In fact, upon hearing Hendrix’s cover for the first time, Dylan reportedly said “It’s Jimi’s now.” Dylan’s version, however, remains a masterclass in lyrical craftsmanship which shouldn’t be ignored. The song features a conversation between a joker and a thief, layered over a repetitive guitar riff that builds a sense of urgency. Dylan’s original recording and Hendrix’s electric reinterpretation together made “All Along the Watchtower” a unique staple in the canon of rock music, covered and beloved by many artists across generations.
5. Hey Mr. Tambourine Man
Bettman/Getty ImagesWith the eternally catchy lyric “Hey Mr. Tambourine Man, play a song for me,” Bob Dylan invites listeners into his lyrical dreamscapes with this song. Symbolic of Dylan’s early folk period in the ’60s, “Mr. Tambourine Man” is a journey through sound as the weary traveler seeking solace in the tambourine’s famous jingle-jangle. It also marked a significant moment in rock history by being one of the first songs to bridge the gap between poetic folk and mainstream pop, especially after The Byrds’ electric rendition hit the charts. Dylan’s version, with its pure acoustic delivery and intricate wordplay, remains a profound call to those who “hear it in the deep heart’s core.”
4. Tangled Up In Blue
Brian Shuel/RedfernsHow else can you describe this song other than a great American novel wrapped up in 5 minutes? With its opening line, “Early one morning the sun was shining,” Dylan sets the scene for a story that captures the complexity of human relationships. It’s a major song is a standout track from his critically acclaimed album Blood on the Tracks, often seen as a reflection of his own life — filled with ups and downs. The shifting viewpoints and the fluidity of the lyrics keep the listener hooked, as the song moves through different scenes as its protagonist shifts from place to place.
3. The Times They Are A-Changin’
John Byrne Cooke Estate/Getty Images“Don’t criticize what you don’t understand” is perhaps one of the most timeless lyrics in the entire Dylan discography. This song emerged as a powerful anthem from Dylan’s earlier work, calling for adaptation in the face of relentless societal shifts. Urging listeners from all walks of life to “Come gather ’round people wherever you roam,” it serves as a rallying cry for awareness and activism, resonating well beyond the tumultuous 1960s civil rights movements it originally echoed.
2. Blowin’ in the Wind
Thomas Monaster/NY Daily News via Getty ImagesBob Dylan poses a series of philosophical questions surrounding human rights, peace, and freedom. Opening with the line, “How many roads must a man walk down before you call him a man?” This song quickly became an anthem for the 1960s civil rights and anti-war movements — yearning for answers that seemed just out of reach, always “blowin’ in the wind.” The simplicity of its melody is what sets it apart, making it not only a staple of folk music but a universal query into the human condition. Dylan’s gentle yet insistent questioning offers no answers, instead leaving the listener to ponder the complexities of justice and equality.
1. Like A Rolling Stone
Steve Morley/RedfernsWith the opening crack of the snare, “Like a Rolling Stone” instantly captures the listener’s attention, signaling a major shift in Bob Dylan’s career and rock and roll itself. Dylan’s lyrics tell the story of a person who has fallen from grace into a humbling new reality, asking, “How does it feel, to be on your own, a complete unknown, like a rolling stone?” This track showed his utilization of electric instruments that drive the song with a raw, infectious rhythm. It’s a piece filled with scorn and sympathy in equal measure, challenging listeners to confront their own perceptions of success and identity. “Like a Rolling Stone” is nothing short of a masterclass in songwriting and impact — a cornerstone of music history that remains a defining anthem of the 1960s.
