Ranking the 5 Best Songs on Bob Dylan’s Comeback Masterpiece ‘Time Out of Mind’

In 1997, Bob Dylan resurrected his career when he released Time Out of Mind.

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He worked with producer Daniel Lanois on his previous comeback effort, Oh Mercy (1989), but it was more of a creative anomaly than a return to form.

However, Time Out of Mind redefined Dylan for the next chapter of his career. He followed it with a run of brilliant studio albums, avoiding the creative drought between Oh Mercy and Time Out of Mind.

Following Jerry Garcia’s death in 1995, Dylan examined his own mortality and wrote a collection of songs about love, redemption, and death. Lanois and engineer Mark Howard shaped the album at Teatro, a makeshift studio in Oxnard, California. Howard manipulated Dylan’s voice using guitar amps to create a gritty sound, while Lanois washed the band in cascades of echo and reverb. Dylan sounded like he was singing from another dimension.

Though the job here is to highlight the five best songs on his masterpiece, it’s a good idea to play the whole album. Nevertheless, here are Time Out of Mind’s five best songs ranked.

5. “Can’t Wait”

The sessions for Time Out of Mind started with drum loops. Lanois and drummer Tony Mangurian recorded percussion parts over Charley Patton’s Delta blues. They removed Patton’s recordings and edited their parts into loops for Dylan. The idea to work this way began with Beck. After hearing Odelay, Dylan said, “I’d love to make a record like that kid Beck.” Though the sessions evolved away from using loops to build the album’s structure, a Beck-like groove remains on “Can’t Wait.” Lanois prefers the song’s original demo, but the final rhythmic arrangement of “Can’t Wait” hints at the album’s original architecture.

Skies are grey, I’m looking for anything that will bring a happy glow
Night or day, it doesn’t matter where I go anymore, I just go
If I ever saw you coming, I don’t know what I might do
I’d like to think I could control myself, but it isn’t true
That’s how it is when things disintegrate
And I don’t know how much longer I can wait

4. “Standing in the Doorway”

The album’s third track, “Standing in the Doorway,” is utterly beautiful, with Dylan singing about dying happiness. Early in the song, he croons about the ghost of old love. However, in a later verse, Dylan admits, I would be crazy if I took you back. It’s a profound line on an album full of profound lines. Someone once described the band on Time Out of Mind as being like Noah’s Ark—there were two of each instrument. But Lanois coached them to play with discipline. He also instructed the musicians to stop playing when they felt lost. Dylan often changed arrangements on a whim, confusing even the most experienced players. Part of the album’s charm is hearing them avoid crashing into each other.

I’m walking through the summer nights
Jukebox playing low
Yesterday everything was going too fast
Today, it’s moving too slow

3. “Love Sick”

Dylan opens the album with what sounds like parting words. It’s Dylan walking along Desolation Row—the ultimate outsider—and he’s sick of love. He’s burdened by the ticking clock, which the pulsing organ mimics with the urgency of fleeting time. “Love Sick” establishes the despairing mood of Time Out of Mind. While he stares at two lovers, he’s left hanging on to a shadow of affection. A variation of the love hurts theme.

I’m walking through streets that are dead
Walking, walking with you in my head
My feet are so tired, my brain is so wired
And the clouds are weeping

2. “Make You Feel My Love”

“Make You Feel My Love” is the light peeking through Dylan’s melancholy. He sings tenderly over a piano and woozy organ, and his weary voice adds poignancy to the song. Billy Joel released a soft rock version one month before Dylan released Time Out of Mind. In 1998, Garth Brooks recorded a country rendition for the Hope Floats soundtrack. Adele’s version appeared on her debut studio album 19. “Make You Feel My Love” is similar to Leonard Cohen’s “Hallelujah,” a great song in danger of ruin from too many reality TV singing shows. But Dylan’s original is untouchable, and Lanois’ ghostly treatment adds to its haunting beauty.

When the rain is blowing in your face
And the whole world is on your case
I could offer you a warm embrace
To make you feel my love

1. “Not Dark Yet”

Dylan’s character in “Not Dark Yet” reaches the twilight of his life with growing cynicism. It’s a tale of the spiritual death of a man slowly giving in to nihilism. The warm organ turns the song into a misty hymn where the instruments bleed into each other like the hazy memories of fading years. He’d written many death-beset songs before, including “Knockin’ on Heaven’s Door” and “Let Me Die in My Footsteps.” But Dylan felt death was catching up to him, and “Not Dark Yet” turns abstract mortality into a hard truth.

Well, my sense of humanity has gone down the drain
Behind every beautiful thing, there’s been some kind of pain
She wrote me a letter, and she wrote it so kind
She put down in writing what was in her mind
I just don’t see why I should even care
It’s not dark yet, but it’s getting there

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Photo by Vinnie Zuffante/Getty Images

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