Video Vanguard: Essential Pieces of Bob Dylan’s Life Are Laid Out in “When the Deal Goes Down”
In the ‘60s home movie-style music video for “When the Deal Goes Down,” Bob Dylan finds solace amid life’s turmoils by reflecting on the objects that shaped his youth.
Written by Joseph Gonzalez
Photos courtesy of Chris Bowman and Bob Dylan
By 2006, folk music legend Bob Dylan had amassed an iconic body of work and a persona considered almost mythological.
The release of his album Modern Times that year indicated a transition into the final stage of his career. This last lap in the music business, particularly for an introspective artist like Dylan, can mirror the last stages of life, as the narrative of one’s journey finally becomes clear and decipherable. One’s persona is more or less defined, and the events that shaped the trajectory of their life starts to make sense in retrospect.
For Dylan, this period was a time for reflection. The first volume of his autobiography was published two years earlier in 2004, and his music started to increasingly resemble the very styles that inspired him in his youth.
This nostalgia-inducing act of reflection can either distract from the inevitable end of life or celebrate what has defined one’s existence. Dylan’s work reflects the latter, as exemplified in his song and video for “When the Deal Goes Down” from Modern Times.
The ballad opens with a brief, romantic steel pedal intro, evoking sentimentality. Filmed on grainy 8mm film, the footage immediately catches the eye of the viewer. The shaky, unpolished quality isn’t meant to look professional but intentionally evokes the feel of handheld home video footage, an artistic decision that creates an undeniable sense of nostalgia.
The first shot introduces the video’s main character, a woman played by 22-year-old Scarlett Johansson, as she rides a ferry past the Statue of Liberty. It’s the 1960s, the decade in which Dylan blossomed into fame, becoming music’s fastest-rising star.
“In the still of the night, in the world's ancient light / Where wisdom grows up in strife /
My bewildering brain, toils in vain / Through the darkness on the pathways of life,” Dylan sings as the woman smiles and waves to the camera. Dylan admits that, despite the “wisdom” he has gained as he’s aged, he still feels lost. The progression of life remains dark and mysterious, but he chooses to dive into the uncertainty, bolstered by the support of something or someone.
“We live and we die, we know not why / But I'll be with you when the deal goes down,” he assures. The “you” could be a romantic partner, a higher power, or simply a feeling of hope — whatever it is, it shows Dylan life’s meaning.
The woman now rides in the passenger seat of a cherry-red convertible, the kind of car the singer bought with his first big paycheck. The car has Minnesota license plates, a reference to Dylan’s roots. He lived in the state for the first 19 years, and his earliest public performances were around the University of Minnesota.
“The midnight rain follows the train / We all wear the same thorny crown / Soul to soul, our shadows roll,” Dylan quavers as the woman walks through a green meadow. Scenes roll by, showcasing the woman at home: lying with a dog, playing badminton (a sport Dylan has played since the 1950s), visiting an aquarium, and holding a toddler.
For Dylan, the pains of the human condition exist alongside life’s beauty. The inescapable train of time rolls onward through generations, each carrying the shadow of their predecessors.
The woman now looks through old photos with an older couple, presumably her parents. The mother holds up a picture of her as a young woman to the camera. The shot cuts to a close-up of Johansson’s face.“We learn to live and then we forgive / O'er the road we're bound to go / More frailer than the flowers, these precious hours,” Dylan croons over the sentimental chord progression.
The woman now spends her precious hours on a small boat, dreamily running her fingers across the moving water. She fishes and catches a trout, another hobby from the folk singer’s youth.
In a hammock, the woman reads “Bound For Glory,” Woody Guthrie’s autobiography. This book was the gateway for Dylan to Guthrie’s music. A year after reading it, Dylan set off to New Jersey to visit Guthrie at the Parkland Psychiatric Hospital. He played his song, “Song to Woody,” for Guthrie, which would soon appear on Dylan’s debut album.
The video also features a shot of the album cover of Hank Williams’ Wanderin’ Around, released in 1961 — the same year Dylan visited Guthrie. Williams, along with Guthrie, was one of the most influential musical figures in Dylan’s life. By age 11, Dylan was transfixed with Williams’ music. His cutting, clean melodies, and knack for simple poeticism inspired Dylan to write his own songs.
“I became aware that in Hank’s recorded songs were the archetype rules of poetic songwriting,” Dylan wrote in his 2004 autobiography. “The sound of his voice went through me like an electric rod.”
A mellow guitar solo leads into a bizarre sequence as the woman visits a haunted house at a carnival, a setting that holds a meaningful place in Dylan’s life. According to the singer, as a teenager, he traveled across the country with a carnival, working odd jobs like cleaning up after the animals and learning folk songs on his guitar along the way. Some dismiss Dylan’s alleged time with the carnival as pure fantasy, but it’s clear that the archetype of the carnival had a lasting impact on the way he saw the world.
“I heard a deafening noise, I felt transient joys / I know they're not what they seem / In this earthly domain, full of disappointment and pain / You'll never see me frown,” Dylan proclaims as the video takes a brief, ghostly turn.
Strange animal-masked figures slow dance, and it cuts to a dimly lit poster of Buddy Holly on a table — a poignant reference to the time Dylan saw Holly perform in 1959, just three days before Holly tragically died in a plane crash.
Performers in pink dresses and white face paint — similar to Dylan’s white face paint he wore during the ‘Rolling Thunder Revue’ tour — are shown performing an off-putting, choreographed dance as they sway back and forth, holding what looks like theatrical comedy masks on sticks.
The carnival, defined by its oddities, surely made an impression on Dylan. His fixation with abnormal characters such as the sword swallowers and tightrope walkers appears in some of his most iconic songs.
In an interview with Retrospective Magazine titled “The Austin Interview,” Dylan likened himself to a “trapeze artist,” rather than a songwriter or poet.
The video turns again to the woman, and in the final shot, she returns to her boat. She poses for the camera, now serious and resolute, occasionally saying something to someone off-camera. The camera slowly and shakily zooms in toward her face, capturing her determination.
“I owe my heart to you, and that's saying' it true / And I'll be with you when the deal goes down,” Dylan ends.
The song concludes with the same romantic steel pedal riff from the start, a reminder that Dylan still writes with the same emotional depth as he did at the beginning of his career. He has always taken what he’s gathered from life — whether by coincidence or fate — and turned it into something enduring.
“When the Deal Goes Down” and its corresponding video paint an impressionistic portrait of Bob Dylan’s life. It plays like a dream, with his essence wrapped up in fleeting, captured moments. Through the imagery of a young mother from the ‘60s, the video honors the physical mementos of his artistic youth. These idols taught Dylan how to live, and thus, define his life. In essence, it’s an ode to his distinct and unbounded journey.
Perhaps, when he looks back, Dylan sees himself as this woman, or maybe as the person behind the camera, documenting his own memories through dreamy reflection. Everyone comes to cherish the things that showed them what it's like to love, to feel joy, and even to feel sadness. Many come to identify these things with themselves and their self-identity. The strange and personal body of work Dylan has left behind reflects the peculiar upbringing and collection of experiences which molded his psyche. His weapon against the inevitable injustices of existence has always been the poetry of his songs. The unknowability of his lyrics mirrors the unknowability of the human spirit. His work has always pointed towards the unfathomable, and what helps him find meaning and move past the confusion and pain of living is a sense of spiritual connection. This comfort allows him to continue creating, knowing his image and songs will continue the cycle and spark the creative impulse of future artists.
In this way, Dylan is immortal, his past loves never leaving his side. They are as intimate as family, and in the mental projection of his own memories, they are given the most color.
Every frame of the video is imbued with meaning, even if the scenes seem scattered or nonsensical, much like life itself. The closer one gets to Dylan, the more meaningful one’s relationship will be to this video. The music video for “When the Deal Goes Down” is not just a visual journey, but a reflection of Dylan’s complex relationship with time, memory, and the power of his created mythos.