The Story of Bob Dylan in 20 Songs

Before you see the biopic ‘A Complete Unknown,’ check out these classic Dylan tunes

Eric Spitznagel,

AARP

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Published December 20, 2024

A black and white portrait of Bob Dylan in front of a microphone with a harmonica

Before watching “A Complete Unknown” read about the life of Bob Dylan, told through 20 of his classic songs.

Val Wilmer/Redferns/Getty Images

A Complete Unknown, the much-anticipated new biopic about singer-songwriter Bob Dylan — it opens Christmas Day with Timothée Chalamet in the starring role — promises an intimate portrait of one of the most beloved (and sometimes divisive) artists in music history. But if you’re already familiar with Dylan’s vast canon, which spans more than 60 years, you know that he’s already told his life story in his songs. Although he doesn’t always agree. “I don't write confessional songs,” he once wrote. “It only seems so, like it seems that Laurence Olivier is Hamlet.” If you’re willing to look between the lines, however, the real Dylan is definitely in there.

As we count down to the movie’s premiere, here are 20 classic Dylan songs worth revisiting. They offer a glimpse into the man behind the myth, and the remarkable story of how he went from a “complete unknown” to a cherished Nobel Prize-winning legend.

1. “Highway 61 Revisited” (1965)

In his 2004 memoir Chronicles: Volume One, Dylan wrote about the importance of U.S. Highway 61, which at that time ran from Duluth, Minnesota — where he was born — down to New Orleans. "I always felt like I'd started on it, always had been on it, and could go anywhere from it," he wrote. “It was my place in the universe, always felt like it was in my blood.” The road that “begins about where I began” went on to be featured not just in this classic song, but also as the title of his sixth album.

2. “Song to Woody” (1962)

Just five days after arriving in New York in 1961, 19-year-old Dylan tracked down folk trailblazer Woody Guthrie at the home of friends near Greystone Park Psychiatric Hospital in New Jersey, where the singer was being treated for Huntington's disease. During their meeting, Guthrie reportedly told Dylan, “Kid, don’t worry about writing songs; work on your singing.” Inspired by the encounter, Dylan wrote “Song to Woody” for and about his musical hero, which was one of only two original songs on his 1962 debut. (The other is “Talkin’ New York.”)

3. “The Times They Are A-Changin’” (1964)

Dylan was never a fan of the “spokesman of a generation” label, but this anthem from his 1964 album of the same name cemented that legacy nonetheless. “Your sons and your daughters are beyond your command,” he famously sang to the parents of baby boomers. “Your old road is rapidly agin’.” It was a rallying cry for a young generation and a master class in political songwriting, and because it was released just months after the assassination of John F. Kennedy, it had an urgency that pop music rarely matched. “I wanted to write a big song,” Dylan explained in the liner notes of his 1985 box set Biograph. “With short concise verses that piled up on each other in a hypnotic way.” Mission accomplished.

4. “My Back Pages” (1964)

As Rolling Stone magazine noted in 2020, “My Back Pages” was “the sound of the greatest protest singer of the Sixties leaving politics behind.” Dylan himself seems to agree with the assessment, telling The New Yorker in 1964 that he was done with being a “spokesman” and writing songs that pointed at “all the things that are wrong.” Watching him record “My Back Pages” — in which Dylan sings “I was so much older then, I’m younger than that now” — writer and music critic Nat Hentoff noted that it seemed to “express (Dylan’s) current desire to get away from ‘finger-pointing’ and write more acutely personal material.”

5. “Ballad in Plain D” (1964)

“I must have been a real schmuck to write that,” Dylan once told an interviewer about this song from the 1964 album Another Side of Bob Dylan. “Of all the songs I’ve written, maybe I could have left that alone.” It recounts his painful breakup with his first serious girlfriend, Suze Rotolo — the same woman who huddled with him on the cover of 1963’s The Freewheelin’ Bob Dylan. For a songwriter who often hid his true meaning in symbolism, this one was raw and full of real anger and hurt.

6. “Positively 4th Street” (1965)

When a Dylan song opens with a line like, “You’ve got a lot of nerve,” you know you’re in for some serious literary venom. Named for 4th Street in New York City, the epicenter of the Greenwich Village folk scene of the ‘60s, it’s where Dylan first made his name — and it’s the place that turned against him when he dared to pick up an electric guitar and make pop music. “Positively 4th Street” is a “sneering excoriation” of his former folk family, The Guardian wrote in 2020.

7. “It’s All Over Now, Baby Blue” (1965)

On July 25, 1965, Dylan shocked his fanbase by “going electric” at Rhode Island’s Newport Folk Festival, playing part of his set with a full electric band. The audience booed, with one famously shouting, “Judas!” “I couldn’t understand it,” Dylan told SPIN magazine in 1985. “I was a little embarrassed by the fuss because it was for the wrong reasons.” He finished his performance with two acoustic songs, including this one from the newly released album Bringing It All Back Home. It was “his hard-ass response” to the critics, as Rolling Stone summed up the moment.

8. “Fourth Time Around” (1966)

Dylan and the Beatles had a love-hate relationship. Dylan famously introduced the Fab Four to marijuana. But he also wasn’t happy when he suspected the Beatles were ripping off his ideas. After hearing the Beatles hit “Norwegian Wood,” written and sung mostly by John Lennon, Dylan reportedly said, “What is this? It’s me, Bob. [John’s] doing me!” If you believe some critics, Dylan wrote “Fourth Time Around” to openly mock Lennon’s attempts at imitating him. Lennon may have gotten the message, revealing in a 1968 Rolling Stone interview that he “didn’t like” Dylan’s song. “I was very paranoid. I just didn’t like what I felt I was feeling.”

9. “Day of the Locusts” (1970)

During the spring of 1970, Dylan traveled to Princeton University to accept an honorary Doctorate of Music degree. “Bob did not want to go," his friend and fellow musician David Crosby remembered. "I said, ‘C’mon, Bob, it’s an honor!’” Dylan begrudgingly agreed to attend, and his experience resulted in this song about the cicadas that almost drowned out the outdoor ceremony. Although it’s unlikely that, as the lyrics suggested, Dylan was seated next to a man whose “head was exploding,” the rest feels like a snapshot from a very surreal day.

10. “You Ain’t Goin’ Nowhere” (1975)

After his 1966 motorcycle accident, Dylan holed up in upstate New York, where he and his backing band the Hawks (who would later become the Band) laid down rough demos for songs never intended to be shared with the outside world. “That's really the way to do a recording,” he told Rolling Stone in 1969. “In a peaceful, relaxed setting, in somebody's basement. With the windows open … and a dog lying on the floor.” One version of the song, released in 1975 on The Basement Tapes, sums up perfectly his feelings of isolation during that time. “Strap yourself to the tree with roots/You ain't goin' nowhere,” he sings.

11. “Forever Young” (1974)

Although Dylan insisted in the Biograph liner notes that he was "not wanting to be too sentimental” when writing "Forever Young,” it’s impossible to listen to it and not get a little choked up, especially if you’re a parent. "May you grow up to be righteous/ May you grow up to be true/ May you always know the truth/ And see the lights surrounding you." Dylan, who at the time was a father to two daughters and three sons, hasn’t recorded many songs about parenting, but this one tells you everything you need to know about him as a father .

12. “Sara” (1976)

Dylan wrote several songs about or inspired by his first wife, Sara Lownds. Some, like "Sad Eyed Lady of the Lowlands," were so steeped in literary allusion that it could be difficult to understand what he was sharing about their relationship. But with “Sara,” the closing song on his 1976 album Desire, he wore his heart on his sleeve, directly addressing his “radiant jewel, mystical wife.” Sara herself showed up to the studio to watch him record it, and before Dylan played the first note, he reportedly looked at her and said, “This one’s for you.” No ambiguity there.

13. “Tangled Up in Blue” (1975)

“The songs are my parents talking," Jakob Dylan once said about his father's 1975 album Blood on the Tracks. Dylan himself has denied that anything on the album, including this memorable opening track, is based on his doomed marriage. He even insisted at one point that the songs were actually inspired by Russian writer Anton Chekhov’s short stories. He might be telling the truth, or maybe not. He often introduced “Tangled Up in Blue” in concert by saying, “[This song] took me 10 years to live, and two years to write.”

14. “Oh, Sister” (1976)

Dylan’s relationship with fellow singer/songwriter Joan Baez, both professionally and romantically, is the stuff of folk music legend. And Dylan has only occasionally given his audience a peek into their rocky past. On this 1976 track from Desire, he appears to address a sister, asking her if he’s still “deserving of affection.” But Dylan didn’t have a sister. Could he have been talking about Baez? She seemed to think so, responding directly to him with her own similarly named song, “O Brother,” in which she sings: “And would you kindly tell me, mister/ How in the name of the Father and the Son/ Did I come to be your sister?”

15. “Every Grain of Sand” (1981)

Dylan’s “born again” period resulted in three albums devoted to his newfound Christian faith: Slow Train Coming (1979), Saved (1980) and Shot of Love (1981). Although fans and critics alike weren’t crazy about his religious music, there are a few standout songs, like this gem that even Dylan described as “inspired,” adding that while writing it, “I felt like I was just putting words down that were coming from somewhere else.” As U2 singer Bono once wrote about the song, “It’s like one of the great Psalms of David. Dylan stops wailing against the world, turns on himself and is brought to his knees.”

16. “Not Dark Yet’ (1997)

Mortality was very much on Dylan’s mind in 1997. His friend and collaborator Jerry Garcia of the Grateful Dead passed away from a heart attack a couple of years earlier. And just months before the release of Time Out of Mind, on which “Not Dark Yet” is featured, Dylan was hospitalized with pericarditis, a severe heart infection that had him convinced he'd “be seeing Elvis soon.” The song is full of dark humor and existential dread, reflected perfectly in Dylan’s world-weary voice. “I was born here and I'll die here against my will,” he sings. “I know it looks like I'm moving, but I'm standing still.”

17. “Things Have Changed” (2000)

The song that won Dylan his first (and thus far only) Academy Award. He once described “Things Have Changed” — which was featured in the 2000 movie Wonder Boys — as “a song that doesn't pussyfoot around nor turn a blind eye to human nature.” Critics, meanwhile, have had slightly different interpretations. Rolling Stone hypothesized that it was “a harsh riposte” to the political songs that once defined Dylan, and was “basically the evil twin” of anthems like “The Times They Are A-Changin’.”

18. “Mississippi” (2001)

“Your days are numbered, so are mine,” Dylan sings at the beginning of this exploration of aging and regret. Dylan loved the song enough that he not only released an official version on the 2001 album Love and Theft, but three different outtakes on 2008's Tell Tale Signs: Rare and Unreleased. Singer/songwriter Sheryl Crow, one of a dozen artists who covered what many believe is among Dylan’s best songs, once wrote that “Mississippi” is “our introduction to Dylan as somebody facing mortality with an upbeat attitude.”

19. “Autumn Leaves” (2015)

Nobody expected Dylan’s third act to involve covering standards from the Great American Songbook. But that's exactly what we got with his trio of albums, Shadows in the Night (2015), Fallen Angels (2016) and Triplicate (2017). No song better personified this period than his take on the romantic ballad “Autumn Leaves,” a jazz classic from 1945 that’s been recorded by everyone from Frank Sinatra to Bing Crosby to Doris Day. Dylan, who was 73 when he recorded it, clearly feels an affinity for the song; he’s performed it live 237 times (as of this writing), making it one of his most frequently played cover song of all time.

20. “I Contain Multitudes” (2020)

Released during the pandemic, this second single from the album Rough and Rowdy Ways feels like a return to classic Dylan, with its wordplay and literary name-checking, and the aging poet “considering his place in the constellation of great musicians and artists through the ages,” according to Rolling Stone. In a 2020 interview with The New York Times, Dylan described the song as “trance writing. It’s the way I actually feel about things. It is my identity and I’m not going to question it, I am in no position to.”

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Eric Spitznagel is a features writer for AARP Members Edition. He was also a co-founding editor of The Arrow, AARP’s newsletter for Gen X men. He's been a regular contributor to magazines like Vanity Fair, Men's Health, Rolling Stone, and The New York Times, among others.