Few things will inspire interest in a legendary artist’s back catalog than a prestigious biopic with a respected director, a movie star going all-in on the role, and of course, the cooperation of the artist’s estate and publishers (so the most iconic songs can be licensed for the film). 

Some obvious examples are the 2004 Ray Charles biopic Ray directed by Taylor Hackford and starring Jamie Foxx; the 2005 Johnny Cash biopic Walk The Line, directed by James Mangold and starring Joaquin Phoenix; 2018’s Freddie Mercury biopic Bohemian Rhapsody, directed by Bryan Singer and starring Rami Malek and 2022’s Elvis Presley biopic Elvis, directed by Baz Luhrmann and starring Austin Butler. All of them got Academy Award nominations (and some were winners, including Malek and Foxx). 

The Bob Dylan biopic  A Complete Unknown, a film directed by James Mangold and starring Timothee Chalamet, seems destined to be a big Oscar nominee in 2025. It’s based on the 2015 book Dylan Goes Electric! which details Bob Dylan’s artistic evolution, starting with his days as a folk singer and leading up to his infamous and controversial performance at the Newport Folk Festival on July 25, 1965, when he showed up with an electric rock band (this was considered heresy in folk circles at the time).

(Fun fact: Tom Morello, an electric guitar player of some note, has said “I may be the last person alive who still believes that Dylan sold out at Newport in 1965 when he went electric. The pressure was on him to lead a movement, something he didn’t sign up for and wasn’t interested in.”) 

As sort of a “pre-game” to seeing the film, we thought we’d take a look at some Dylan’s best songs from the era. It’s not a comprehensive list – we’ve done a list like that already – and we’ll leave off the songs that everyone knows, like “Blowin’ In The Wind,” “The Times They Are A-Changin’” and “Like A Rolling Stone.” This is not a ranking, it’s just a list of some gems you may not be familiar with.

• “Talkin’ New York” from ‘Bob Dylan’ (1962)

  Many fans mistakenly refer to 1963’s The Freewheelin’ Bob Dylan as his debut because it contains many of his greatest songs, like “Blowin’ In The Wind.” Bob Dylan, meanwhile, was mostly covers of folk and blues songs. It contained material that many folk singers of the day would be familiar with: “In My Time Of Dyin’,” “Man Of Constant Sorrow.” “Fixin’ To Die” and “House Of The Rising Sun,” among others. But the album had two Dylan originals: the first was “Talkin’ New York,” which describes his arrival in New York from his home in Minnesota. After arriving in Greenwich Village, he tells us, “I walked down there and ended up/In one of them coffee-houses on the block/I get on the stage to sing and play/Man there said, ‘Come back some other day: You sound like a hillbilly/We want folksingers here!’” New York hipsters: insufferable for more than sixty years running! But obviously, the people at the coffee houses came around to Dylan’s “hillbilly” sound. 

  
  
  

• “Song To Woody” from ‘Bob Dylan’ (1962)

  The other Bob Dylan original from his debut album was a tribute to the legendary folk singer Woody Guthrie. Woody Guthrie wrote “This Land Is Your Land,” among many other timeless songs. In Dylan’s 2004 memoir Chronicles Volume One, he wrote. “The songs of Woody Guthrie ruled my universe.” In that book, Dylan recalls going to visit Woody Guthrie at the Greystone Park Psychiatric Hospital in New Jersey, where he was being treated for Huntington’s disease. In A Complete Unknown, there’s a scene where Dylan performs the song for Gurthie in his room: He sings, “Hey, hey, Woody Guthrie, I wrote you a song/’Bout a funny ol’ world that’s a-comin’ along/Seems sick and it’s hungry, it’s tired and it’s torn/It looks like it’s a-dyin’ and it’s hardly been born.”

  A fascinating part of Chronicles is when Dylan recalls Guthrie telling him about boxes of poems and unused lyrics in the basement of his house in Coney Island. As Dylan recalls, Guthrie told him, “I was welcome to them.” So he trekked out to Guthrie’s house on a frigid winter day to find those lyrics. When he got there, Woody’s wife wasn’t home. However, his young son, Arlo (who would become an artist, and would have a huge Thanksgiving hit with “Alice’s Restaurant”) was with a babysitter and didn’t know where the box was. Four decades later, those lyrics were used by British folk singer Billy Bragg and American indie rock band Wilco on their Mermaid Avenue albums.

• “Tomorrow Is A Long Time” (recorded live in 1963, released in 1971 on ‘Bob Dylan’s Greatest Hits, Vol II’)

  A lovely song that may have been lost to the mists of time, except for the fact that Elvis Presley recorded a cover in 1966 during the sessions for his gospel album, How Great Thou Art. (Elvis had heard a cover of the song by folk singer Odetta.) It was ultimately released on Presley’s 1966 album Spinout. For our money, it’s one of Presley’s best post-’50s recordings. Dylan would later say that it was “the one recording I treasure the most.” Dylan’s life was changed by Elvis Presley, just like most of his peers.

  The song was clearly written by a young, lovestruck guy: “I can’t see my reflection in the waters/I can’t speak the sounds that show no pain/I can’t hear the echo of my footsteps/Or remember the sound of my own name/Yes, and only if my own true love was waitin’/And if I could hear her heart a-softly poundin’/Yes and only if she was lyin’ by me/Then I’d lie in my bed once again.”

• “Talkin’ John Birch Paranoid Blues” (recorded live in 1962, originally released on 1963’s ‘The Freewheelin’ Bob Dylan,’ but soon removed from reprints, and later released on 1991’s ‘The Bootleg Series Vol. 1 - 3’)

  Dylan’s earlier songs had a pretty sharp (and political) sense of humor. The narrator in this song joins the John Birch Society, an actual anti-communist organization of the era that seemed to find communists (“Reds”) everywhere. He starts out by saying that he was “feelin’ sad and kinda blue” and was worried about communists, so he joined the John Birch Society and was very enthused about the mission of exposing the enemy. Maybe a little too enthused. “I heard some footsteps by the front porch door,” he drawls in the song. “I grabbed my shotgun from the floor/Snuck around the house with a huff and a hiss /Saying, ‘Hands up, you communist!”/It was the mailman: he punched me out!”

  Later he goes further down a rabbit hole: “Well, I quit my job, so I could work alone/Got a magnifying glass like Sherlock Holmes/Followed some clues from my detective bag/And discovered red stripes on the American flag: Betsy Ross!/Now Eisenhower, he’s a Russian spy/Lincoln, and Jefferson and then Roosevelt guy/To my knowledge, there’s just one man/That’s really and truly an American/That’s George Lincoln Rockwell/I know for a fact he hates Commies/’Cause he picketed the movie Exodus!”

• “Masters Of War” from ‘The Freewheelin’ Bob Dylan’ (1963)

  One of Dylan’s hardest-hitting songs. Dylan has said that it isn’t so much an anti-war song as a condemnation of what President Eisenhower called “the military-industrial complex” in his 1961 farewell address: “In the councils of government, we must guard against the acquisition of unwarranted influence, whether sought or unsought, by the military-industrial complex. The potential for the disastrous rise of misplaced power exists and will persist.” Dylan comes for them in the first verse: “Come you masters of war/You that build all the guns/You that build the death planes/You that build the big bombs/You that hide behind walls/You that hide behind desks/I just want you to know/I can see through your masks.”

  Throughout the song, he keeps up his assault, noting that they only build things to destroy, they lie and deceive, they create the wars that other people fight, while watching from a safe distance and profiting. He even sings that they make people afraid to have children. “You ain’t worth the blood that runs in your veins,” he spits.

  The final verse is the most chilling and unforgiving: “And I hope that you die/And your death’ll come soon/ I will follow your casket/In the pale afternoon/And I’ll watch while you’re lowered/Down to your deathbed/And I’ll stand o’er your grave/’Til I’m sure that you’re dead.”

• “Don’t Think Twice, It’s All Right” from ‘The Freewheelin’ Bob Dylan’ (1963)

  Even at a young age, Dylan was able to tackle worldly events like war, but also write about matters of the heart. This one was supposedly inspired by his relationship with Suze Rotolo – the woman pictured with Dylan on the cover of the album (and portrayed in the film by Elle Fanning under the fictional name “Sylvie Russo”). Heartbreak really stings when you’re in your early twenties and you feel that in the lyrics to this song: “I’m walkin’ down that long, lonesome road, babe/Where I’m bound, I can’t tell/But goodbye’s too good a word, gal/So I’ll just say fare thee well/I ain’t sayin’ you treated me unkind/You could have done better but I don’t mind/You just kinda wasted my precious time/But don’t think twice, it’s all right.” Ouch!

  The song has resonated over the decades: In the ‘60s it was covered by folk trio Peter, Paul and Mary. Country stars including Johnny Cash, Dolly Parton and Willie Nelson have also recorded their own versions. A pre-stardom Post Malone covered it (you can find that version on YouTube), as has Lana Del Rey. For our money, the best cover, though, is the one that Eric Clapton played at the Bob Dylan 30th anniversary celebration at Madison Square Garden back in 1992.

• “The Ballad Of Hollis Brown (Live At Carnegie Hall, New York, NY - October 1963)

  The studio version would later be released on 1964’s The Times They Are A-Changin’. It’s one of Dylan’s bleakest and most disturbing songs. It tells the tale of a farmer who has fallen on hard times: “He lived on the outside of town/With his wife and five children/and his cabin fallin’ down.”

  It’s a dire tale of how poverty can lead to desperation and to serious mental illness. Hollis Brown is unable to get any work, he’s broke and, as the narrator tells him, “Your children are so hungry/they don’t know how to smile.” It gets worse from there, and the song ends, “There’s seven people dead/On a South Dakota farm/Somewhere in the distance/There’s seven new people born.” While maybe some of the lyrical references are dated, it’s a story that remains frighteningly relevant today.

• “With God On Our Side” from ‘The Times They Are A-Changin’’ (1964)

  Here, Dylan looks at some of the more horrific chapters of history, specifically things that had been done “with God on our side.” He goes back to the New Testament. “Jesus Christ was betrayed by a kiss/But I can’t think for you/You’ll have to decide/Whether Judas Iscariot had God on his side.” But he also addresses the birth of our country (“The calvaries charged/The Indians died/The country was young/With God on its side”), the Spanish-American War, World War I and II, the Cold War and any future conflicts (“But now we got weapons/Of the chemical dust/If fire them we’re forced to/Then fire them we must”). He concludes, “If God’s on our side/He’ll stop the next war.”

• “The Lonesome Death Of Hattie Carroll” from ‘The Times They Are A-Changin’’ (1964)

  A harrowing account of the killing of 51-year old Black barmaid Hattie Carroll by William Zantzinger, “who at twenty-four years [old], owns a tobacco farm of six hundred acres/With rich wealthy parents who provide and protect him/And high office relations in the politics of Maryland, reacted to his deed with a shrug of his shoulders.” The song isn’t totally accurate: while Dylan sings that Zantzinger was charged with first-degree murder, he was actually charged with second-degree murder. (According to The Washington Post, he spent six months in jail for this, and then returned to his life as a wealthy businessman.) But other than that, the cuts to the heart of a painful and tragic story about race in America.

• “Spanish Harlem Incident” from ‘Another Side of Bob Dylan’ (1964)

  I’ll shift to the first person here and recall an interview that I did with the late, great and criminally underappreciated songwriter Chris Whitley back in 2000. His then-new album, Perfect Day, featured all covers, including Dylan’s “4th Time Around” and “Spanish Harlem Incident”; the latter track opened the album. When I asked him about it, he laughed a little and said that it was almost too good to talk about; he didn’t know what to say about the song. He indicated that it set an impossibly high bar for songwriters. Dylan has said that he doesn’t know what the song is about, but looking at it from one angle, it seems like it’s about someone who falls in love with a woman at first sight, without ever actually meeting her.

• “Chimes Of Freedom” from ‘Another Side of Bob Dylan’ (1964)

  Most of the other political songs on this list have a degree of specificity to them; they are about specific things or incidents. “Chimes Of Freedom,” on the other hand, is a more of an anthem for people who are fighting for justice. But as Xavier University’s Graley Herren wrote in his essay, “The Twilight’s Last Gleaming: Dialogs and Debts in Bob Dylan’s ‘Chimes of Freedom,’” “‘Chimes of Freedom’ is at once the high-water mark of Dylan’s achievement as a protest singer and his resignation letter as spokesperson for a political movement he had outgrown by 1964.” Most of Another Side of Bob Dylan were songs about Bob Dylan. There are a few love songs, and as Herren wrote, “‘Chimes of Freedom’ can best be understood as a love song for liberty, a love song for those denied their due share of freedom, and a love song for those dedicated to righting such wrongs.”

• “Mama, You Been On My Mind (with Joan Baez)” from 'The Bootleg Series Vol 6: Concert At Philharmonic Hall'

  Dylan and Joan Baez’s relationship is a big plot point in A Complete Unknown (in the trailer, we see them perform together, then making out and then him insulting her songs; Joan, played by Monica Barbaro, retorts, “You’re kind of an a–hole, Bob,”). This concert, recorded on October 31, 1964 at New York’s Philharmonic Hall, was mostly Dylan solo acoustic (as all of his shows were back then), but Baez joined him towards the end of the show. It’s a bit loose, as you can hear in this song. This show found Dylan in a transitional phase; a lot of the songs in the setlist were from his next album, 1965’s Bringing It All Back Home, which saw him moving away from his protest-folk persona. Another scene in the trailer sees Dylan annoyed that “They just want me singin’ ‘Blowin’ In The Wind’ for the rest of my God-damned life.” But he would soon let the world know that he was no longer that guy.

• “Subterranean Homesick Blues” from ‘Bringing It All Back Home’ (1965)

  This is really where Dylan “went electric.” It’s the opening track from Dylan’s fifth album, and the one that started the phase of his career as a post-folkie rock and roller. This song owed a debt not to Woody Guthrie or Josh White, but to Chuck Berry and Beat poet Allen Ginsberg. It was as radical of a “new direction” as any popular musician has ever taken. It was Dylan’s first top 40 hit, and of course, was seen as a “sell-out” by the folkies.

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