Advent is my favorite season of the liturgical year. It is a season of expectation, preparation, and self-reflection. The Church meditates on the mystery of the Incarnation at Christ’s first coming while considering his second coming. So we turn our attention inward where, to the best of our ability, we disclose those parts of us requiring to be handed over to the Refiner’s Fire for purgation (Mal 3:2). In Advent the reality of divine judgment gives significance to our actions and the crushing weight of eternity contextualizes our temporality.

Recently, I have been more intentional in the way I listen to music. Instead of listening to custom-made playlists at the mercy of shuffle mode, I have been slowly exploring the catalogues of artists. My current selection has been the work of Bob Dylan, an appropriate choice for the Advent season. With a catalogue as large as his, I will focus on his first album from 1962.

The self-titled debut album Bob Dylan focuses on themes like disappointment, failure, and mortality. Lacking the counter-cultural pacifistic zeal present in The Freewheelin’ Bob Dylan, this album is more intimate. The focus is not on political problems “out there” so much as on the singer-storyteller’s immediate orbit, teaching the listener a certain transitory view of the world paralleling the focus of Advent. The songs from this album of particular note are “In My Time of Dyin,” “Man of Constant Sorrow,” “Fixin’ to Die,” and “Gospel Plow.”

“In My Time of Dyin’” is a Gospel song initially based on Psalm 41:3 (NRSV), “The Lord sustains them on their sickbed; in their illness you heal all their infirmities.” The song reflects two Advent themes: dependence and preparation. The song speaks to dependence on God:

Well, meet me Jesus, meet me, meet me
In the middle of the air
If these wings should fail me
Lord, won’t you meet me with another pair.

In Advent, we meditate on where we are spiritually lacking and we turn towards God to meet our needs where we know we cannot. While we consider our dependence on God, we also look forward to our finality:

Lord, in my time of dying, don’t want nobody to cry
All I want you to do is take me when I die
Well, well, well, so I can die easy
Well, well, well
Well, well, well, so I can die easy
Jesus gonna make up, Jesus gonna make up
Jesus gonna make up my dying bed

The album’s next Advent-themed song is the folk classic “Man of Constant Sorrow.” The title is an allusion to the Suffering Servant in Isaiah 53:3 who was “despised and rejected by others; a man of suffering and acquainted with infirmity; and as one from whom others hide their faces he was despised, and we held him of no account.” The song itself is about a protagonist who leaves home. Separated from loved ones, he has no place to lay his head, embracing a nomadic mode of being (“Through this open world I’m about to ramble, Through ice and snow, sleet and rain, I’m about to ride that morning railroad, Perhaps I’ll die on that train”). Yet the song ends with a sense of homecoming:

I’m going back to Colorado
The place that I started from
If I knowed how bad you’d treat me
Honey, I never would have come

The song uses biblical imagery of the “man of constant sorrow” as a metaphor for the singer’s personal problems. In so doing, the song speaks prophetically about suffering in that all pain and trial finds its culmination in the crucifixion. However much suffering we go through, the fact that Christ became “like his brothers and sisters in every respect, so that he might be a merciful and faithful high priest in the service of God, to make a sacrifice of atonement for the sins of the people” (Heb 2:17; cf. Phil 2:8). However much we suffer, Christ is the Man of Constant Sorrow. As Danielle Cummins expresses beautifully, “We find [the suffering God] at our side, mending our story with His anew and deepening our devotion to a crucified and risen Messiah.”

“Fixin’ to Die” is the album’s next tune which speaks to Advent. The song grapples with the tension between love of life and the inevitability and uncertainty of death:

Feelin’ funny in my mind Lord, I believe I’m fixin’ to die
Feelin’ funny in my mind Lord, I believe I’m fixin’ to die
Well I don’t mind dyin’ but I hate to leave my children cryin’
Well look over yonder, to that buryin’ ground
Look over yonder, to that buryin’ ground
Sure seems lonesome, Lord when the sun goes down

Advent is a season of seemingly contradictory impulses. While considering darkness, we meditate on light. While thinking about death, we yearn for life. Even though our contemplation of the end may cause us momentary hesitation, Advent is a time for training. Anglican poet John Donne explains, “The church prepares our devotion before Christmas Day with four Sundays in Advent, which bring Christ nearer and nearer to us and remind us that he is coming to enable us by a further examination of ourselves to depart in peace, because our eyes have seen his salvation.”

The song with the most overt religious theme on the album is “Gospel Plow.” The title comes from Luke 9:62 where Jesus says, “No one who puts a hand to the plow and looks back is fit for the kingdom of God.” The song uses a framework of eternity to bring significance to present actions:

Mary, Mark, Luke and John
All these prophets are dead and gone
Keep your hand on that plow, hold on
Oh Lord, oh Lord, keep your hand on that plow, hold on
Well, I’ve never been to Heaven
But I’ve been told streets up there
Are lined with gold
Keep your hand on that plow, hold on
Oh Lord, oh Lord, keep your hand on that plow, hold on

As Christians, we work with eschatological hope in mind. We may not see it, but heaven makes our present reality meaningful and, hopefully, keeps our hands on the plow as we work for the kingdom.

In Advent, members of the Church set aside time for self-reflection as we consider the first coming of our Lord in the Incarnation and expect his second coming in judgment. We know that this reality is imminent. Bob Dylan’s first album gives us opportunity to reflect well this season as it confronts us with the reality of suffering, mortality, and ultimately hope.