Folk singer Bob Dylan has been one of the most influential musicians of the 20th and 21st centuries. Over his 60-year career, Dylan has released 39 studio albums, nearly 100 singles, and 15 live albums. Choosing the best songs from one of the most talented songwriters in history is almost impossible—but these 45 tracks come as close as it gets.
1. The Times They Are A-Changin’
The Times They Are A-Changin’ was released through Columbia Records in the 1964 album of the same name. This album, Dylan’s third, was his first to feature exclusively original compositions. Dylan sings about the contemporary social and political struggles against racism, poverty, and for a better world. The song was heavily influenced by Scottish and Irish ballads.
2. Positively 4th Street
Dylan released the single Positively 4th Street through Columbia Records in 1965. It was the follow-up to his highly successful single Like a Rolling Stone. The song’s title is nowhere in the lyrics, leading to debate about its meaning and significance. Its lyrics are bitter and derisive, leading many critics to compare it to his preceding single.
3. Subterranean Homesick Blues
Subterranean Homesick Blues is Dylan’s top song on the album Bringing It All Back Home, released in 1965. It preceded the album’s release by two weeks. Now considered to be among his greatest hits (and was even on Bob Dylan’s Greatest Hits), the song was one of the singer’s first electric recordings and even featured an innovative music video.
4. Just Like a Woman
Released on Dylan’s seventh studio album, Blonde on Blonde, Just Like a Woman was also released as a single. The song debuted on the album in June 1966. It has been criticized for its perceived sexist undertones, which may be a commentary on his relationship with folk singer Joan Baez.
5. Mr. Tambourine Man
Bob Dylan released Mr. Tambourine Man as the first track of the acoustic side of 1965’s Bringing It All Back Home. It quickly became known as one of Dylan’s most popular songs. With its bright melody and surrealist lyrics, Mr. Tambourine Man has been thought to be an analogy to LSD usage.
6. Girl From The North Country
This was Dylan’s second track on the studio album The Freewheelin’ Bob Dylan, later re-recorded as a duet with Johnny Cash. That version would become the opening track for Dylan’s ninth studio album, Nashville Skyline. He wrote it after his first emotional trip to England in 1962, releasing it the next year.
7. Forever Young
Dylan’s 1974 release Forever Young appeared in two versions. Both debuted on Dylan’s fourteenth studio album, Planet Waves. Dylan wrote the song in Tucson, Arizona, in honor of his oldest son, Jesse. The song is a lullaby about Dylan’s hopes for Jesse to stay strong, happy, and blessed.
Hurricane is one of Bob Dylan’s best-known protest songs. He co-wrote it with Jacques Levy for Dylan’s 1976 album, Desire. Hurricane describes a laundry list of racist acts and profiling against the famous boxer, Rubin “Hurricane” Carter. At the time, Carter was imprisoned and wrongfully convicted for murder. (He was released almost 20 years later).
Dylan wrote this ballad with Jacques Levy in July 1975. The second track on Dylan’s Desire was released the next year; Isis is unique among his songs. It contains many references to ancient Egypt (beginning with its titular reference to the Egyptian goddess). Dylan has described it as a song about marriage. The song is styled like a modal folk song and has no chorus.
10. It’s All Over Now, Baby Blue
Written by Bob Dylan for his 1965 album, Bringing It All Back Home, this is one of the performer’s acoustic guitar and harmonica classics. Dylan was influenced by Symbolist poetry. Critics and fans still speculate about the identity of “Baby Blue.” Possibilities include Paul Clayton, Joan Baez, David Blue—or even the audience or Dylan himself.
11. Blowin’ In The Wind
Dylan’s renowned protest song, released in 1963, poses powerful questions about war, peace, and freedom. The chorus is full of ambiguity about what it means to be “blowing in the wind”—does it mean that it is obvious or unattainable? The song, which has been called one of the best of all time, has been inducted into the Grammy Hall of Fame.
12. Like a Rolling Stone
Like a Rolling Stone is one of Bob Dylan’s most famous songs—and perhaps his most widely loved. Dylan originally recorded it during the sessions for his album, Highway 61 Revisited. Columbia Records disliked it and hesitated to release it, citing its heavy electric sound and length. The song leaked as a single and was immediately hailed as revolutionary. It reached No. 2 on the Billboard charts and captured the world’s imagination.
13. Blind Willie McTell
Dylan named this song for the famous blues singer and recorded it in 1983, during the sessions for Infidels, but didn’t release it until 1991. The melody is influenced by the noted jazz song, St. James Infirmary Blues. Dylan played piano with Mark Knopfler playing acoustic guitar. Dylan reflects on the history of American music and slavery, always summing up that “nobody can sing the blues like Blind Willie McTell.”
14. Ballad Of a Thin Man
Dylan wrote Ballad of a Thin Man in 1965. Dylan played the piano himself to contrast with the horror movie style organ parts. The song follows the misadventures of Mr. Jones, who asks questions without answers as the world becomes less sane. Dylan wrote the song in response to people who asked him too many questions for his taste, saying that he wished his life could speak for itself.
15. The Lonesome Death Of Hattie Carroll
Bob Dylan released this topical song in 1964 on his album, The Times They Are a-Changin’. It gives a factual retelling of the murder of a 51-year-old black barmaid named Hattie Carroll at the hands of 24-year-old William Zantzinger, a white man. Zantzinger was sentenced to six months after being convicted of mere assault. He expressed no remorse and openly scorned Dylan until his death. This is now considered one of Dylan’s greatest songs.
16. Sad-Eyed Lady Of The Lowlands
Dylan wrote this song as the closing track for his 1966 album, Blonde on Blonde. The song is longer than many at 11 minutes and 22 seconds, taking up all of the double album’s side four. He wrote the song about his wife, Sara Lownds. Sad-Eyed Lady of the Lowlands is one of the most haunting pop songs of all time.
17. Don’t Think Twice, It’s All Right
This song was released as part of Dylan’s 1963 album, The Freewheelin’ Bob Dylan. It was also released as the b-side of his single, Blowin’ in the Wind. Unlike most of his songs, Dylan’s version is not the most famous. It has been covered numerous times by other top artists, most notably Peter, Paul and Mary. That group’s version made it into the Billboard Hot 100’s Top 10 and popularized the song.
18. My Back Pages
My Back Pages premiered on Dylan’s 1964 album, Another Side of Bob Dylan. It hearkens back to his earliest folk protest songs. It has been interpreted as Dylan moving on from his time in the 1960s folk protest movement, leaving behind his idealism. He only first performed it live 14 years later in the late 1970s.
19. Can You Please Crawl Out Your Window?
This folk rock song debuted as a single in 1965 and reached 58 on the Billboard Hot 100. Dylan never included it on any of his studio albums, though has appeared on some compilations. The blues-inspired folk song notoriously led to an argument between Dylan and Phil Ochs.
20. All Along The Watchtower
Dylan wrote this song for his eighth studio album, John Wesley Harding, in 1967. The lyrics are made up of a conversation between a thief and a joker. Critics continue to argue over what the lyrics mean and symbolize. Some note potential references to prophecies in the biblical Book of Isaiah. It was famously interpreted by Jimi Hendrix for the album Electric Ladyland, released the next year.
21. If Not For You
Dylan wrote If Not For You for his 1970 album, New Morning. The song is a love song to his first wife then, Sara. He recorded it several times in its first year of release with George Harrison shortly after the Beatles broke up. This became a source of widespread speculation in the music industry. Olivia Newton-John covered it the following year—her first hit single.
22. Visions Of Johanna
Dylan wrote Visions of Johanna for his 1966 album, Blonde on Blonde. Critics have often hailed it as one of Dylan’s greatest songwriting achievements. It is often listed among the greatest songs of all time. It has been covered by artists from Marianna Faithfull to Robyn Hitchcock and the Grateful Dead.
23. Every Grain Of Sand
Every Grain of Sand was recorded in 1981 for Dylan’s album Shot of Love and shortly after on the compilation Biograph. Dylan had recently become a born-again Christian in 1978. The song contains many allusions to Jesus and evangelical spirituality. Its imagery is widely considered evocative of the poet William Blake.
24. This Wheel’s On Fire
Dylan wrote This Wheel’s On Fire with Rick Danko and recorded it with The Band in 1967. The Band released their own version in 1968 on the album Music from Big Pink. The Band also released live versions on the double album Rock of Ages and the CD-DVD version, Live at the Academy of Music 1971.
25. Tangled Up In Blue
Dylan recorded Tangled Up in Blue as the opening track for his 15th studio album, Blood on the Tracks. It reached No. 31 on the Billboard Hot 100. The lyrics center on relationships reflected from distinct perspectives. Dylan has changed the lyrics over the years to alter the viewpoints and details of the song.
26. Masters Of War
Dylan’s Masters of War was written for his album The Freewheelin’ Bob Dylan in 1963. The lyrics protest against the nuclear arms race of the Cold War era, which was prominent in many minds at the time. The song contains some of Dylan’s bluntest condemnations and strongest language.
Dylan’s Mississippi is a medium-tempo folk rock piece that serves as the second track on his 2001 album Love and Theft. The song has gravitas with a pop chord progression and similar lyrical themes to Stuck Inside of Mobile with the Memphis Blues Again. Critics often list Mississippi as one of Dylan’s greatest songs.
28. Maggie’s Farm
Dylan recorded Maggie’s Farm for his 1965 album Bringing It All Back Home. Dylan based the song on electric blues, like many of his other pieces at the time. He famously recorded the song in a single take. Every other song on the album has an existing alternative except this one. The song follows a straightforward blues structure full of countercultural war cries.
29. Up To Me
Up to Me is an outtake recording on The Bootleg Series, Vol. 1-3, and 1985’s Biograph. It originated in the session recordings for Blood on the Tracks in 1975. Dylan largely left this song off of his albums, though it is sometimes considered one of his most intriguing and enigmatic songs. For many artists, such a song might have been a career-maker. For Bob Dylan, it’s an outtake.
30. Chimes Of Freedom
Dylan featured Chimes of Freedom on his 1964 album, Another Side of Bob Dylan. The lyrics demonstrate his thoughts as he and a companion shelter from a lightning storm. Dylan sings of his solidarity with the oppressed and downtrodden, hearing the thunder toll in solidarity too. Some critics see it as one of Dylan’s greatest musical contributions and potentially the fruit of reflection on the assassination of President Kennedy.
31. Knockin’ On Heaven’s Door
Dylan wrote this song for the soundtrack of the 1973 film Pat Garrett and Billy the Kid. He released it as a single two months after the film premiered. It soon became a global sensation and reached the Top 10 in numerous countries. It became one of Dylan’s most popular and widely covered songs after the 1960s period. It has been performed by Guns N’ Roses, Eric Clapton, and countless others.
32. Idiot Wind
Dylan released Idiot Wind on the album Blood on the Tracks in 1975. Reviewers have sometimes speculated that Dylan was reflecting on his deteriorating relationship with his wife, Sara. Dylan has said the song is not autobiographical. It received mixed critical reception upon release, though it has received acclaim for its lyrics and performance since.
33. It’s Alright Ma (I’m Only Bleeding)
Dylan released this song on the 1965 album Bringing It All Back Home, and it contains some of the songwriter’s most memorable lyrical images. Dylan details his anger over American hypocrisy, commercialism, consumerism, and preoccupation with war. He ventures into existential questions of personal life at the same time. Dylan has said this is one of his most personally meaningful songs, and he often plays it at his concerts.
34. Simple Twist Of Fate
Dylan’s Simple Twist of Fate was released as the second song on his 1975 album, Blood on the Tracks. The song is about a romantic relationship that is fated to fall apart. The song immediately follows Tangled Up in Blue and similarly begins in the third person before shifting to the first. Critics have ranked it as one of Dylan’s best songs of the 1970s.
35. It Ain’t Me Babe
Dylan released It Ain’t Me Babe on his fourth album, Another Side of Bob Dylan, in 1964. This song is often considered the beginning of Dylan’s more existential explorations of human experience. Johnny Cash famously sang the song as a duet with his future wife, June Carter. Dylan’s biographers concur that he was inspired by his former girlfriend, Suze Rotolo.
36. Lay, Lady, Lay
Dylan released this song on his 1969 album Nashville Skyline. He sings this song, like others on the album, in a low croon instead of his typical high, nasally singing style. Lay, Lady, Lay has become a standard that has been covered by numerous artists. Dylan originally wrote the track for the film Midnight Cowboy but submitted it too late for it to be in the movie.
37. I Dreamed I Saw St. Augustine
I Dreamed I Saw St. Augustine is a song that premiered on Dylan’s 1967 album, John Wesley Harding. Numerous artists covered it, including Joan Baez, on her album Any Day Now and Eric Clapton. The song is a pensive ballad that uses spare musical accompaniment that remains unobtrusive. It was loosely based on the classic ballad I Dreamed I Saw Joe Hill.
38. With God On Our Side
Dylan first performed With God On Our Side during his 1963 debut at The Town Hall in New York City. The lyrics center on Americans’ belief that God is always on their side and opposes their enemies. Dylan mentions the slaughter of Native Americans, the Civil War, the Spanish-American War, both World Wars, the Cold War, and the Holocaust, in conjunction with Judas’ betrayal of Jesus Christ.
Jokerman appeared as the opening track on Dylan’s 1993 album Infidels. It has since appeared in numerous Dylan “Best of” compilations. It is notable for its biblical imagery as a political metaphor. The song failed to chart as a single but was well-received by critics.
40. A Hard Rain’s A-Gonna Fall
Dylan released this song on his second album, The Freewheelin’ Bob Dylan. The lyrical structure of this song is based on the question-and-answer format of traditional ballads. It contains heavy symbolist imagery that communicates suffering amid pollution and war. Dylan said he wrote the song from the initial lines of songs he never thought he’d get around to writing.
41. Murder Most Foul
Based on a quote from Shakespeare’s play Hamlet, Murder Most Foul is Bob Dylan’s 2020 hit. It is the final track on his 39th studio album, Rough and Rowdy Ways. Dylan sings about the assassination of President Kennedy amidst wider American political and cultural history. This was Dylan’s first original piece of music released in eight years. At 16 minutes and 56 seconds, it is his longest song.
42. Desolation Row
Dylan released Desolation Row in 1965 as the final track in his album Highway 61 Revisited. It is one of his longer songs, at 11 minutes and 21 seconds. It is notable for its surreal lyrics, with characters experiencing the effects of entropy and chaos. Desolation Row is often ranked one of Dylan’s greatest musical compositions and one of his most ambitious.
43. I Shall Be Released
Dylan debuted I Shall Be Released in 1991, but he first recorded it with the Band in 1967. It originated with the Basement Tapes sessions. Dylan also released a remixed edition in 2014 on The Bootleg Series Vol. 11: The Basement Tapes Complete. He also recorded the song in 1971 with another arrangement and different lyrics, accompanied by Happy Traum. It is heavily influenced by gospel music and religious imagery.
44. Highway 61 Revisited
Highway 61 Revisited is Dylan’s title track for his 1965 album of the same name. The song is named for Highway 61, which runs to New Orleans, Louisiana from Dylan’s hometown of Duluth, Minnesota. Highway 61 served as a major transit point for Black Americans traveling to northern cities following the Mississippi River valley for up to 1,400 miles.
45. Not Dark Yet
Dylan released Not Dark Yet as the seventh track in his 1997 album, Time Out of Mind. He also released it as a single. The song received widespread critical acclaim when it debuted. The lyric, “It’s not dark yet but it’s getting there,” is interpreted as the narrator, presumably Dylan himself, confronting his mortality.
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