A few critics, including NPR's Tim Riley, drew parallels between the album's title and the Steely Dan song of the same name (first issued on their 1980 album, Gaucho), but the phrase goes back to Samuel Beckett's Lessness, which opens: "Ruins true refuge long last towards which so many false time out of mind." And it includes: "Blacked out fallen open true refuge issueless towards which so many false time out of mind."

In a 1997 interview, Dylan said that the songs on Time Out of Mind "naturally hung together because they share a certain skepticism. They're more concerned with the dread realities of life than the bright and rosy idealism popular today."

In an article published in The Chicago Tribune on September 28, 1997, Greg Kot writes, "Dylan projects the unease of someone adrift in a world that he ceases to understand, and that ceases to understand him. Yet he finds a strange comfort in his surroundings. 'You could say I'm on anything but a roll,' he sings [on 'Highlands'], one of many instances of the album's gallows humor. The music, anchored by Dylan contemporaries such as pianist Jim Dickinson and organist Augie Myers, hovers like an eerie David Lynch soundtrack and echoes the solo-free groove and grind of Dylan's '60s masterpieces. With Lanois' painterly production giving the songs a three-dimensional depth, the arrangements frame Dylan's voice as few recent recordings have.

"Dylan does not push his voice beyond its limits, but rather sing-speaks barely above a hush, as though holding an imaginary conversation with a distant lover, perhaps even his long-departed audience. He sings about love gone cold, but until the epic closing song, 'Highlands,' that loss never acquires a human face. In this 16+ minute epic, the singer briefly recaptures the conversational, playful and erotically charged tone of his youth.

"If the Dylan of World Gone Wrong echoed Flannery O'Connor, the Dylan of Time Out of Mind evokes playwright Samuel Beckett and his spare, unsentimental poetry of despair. He is confident of only one thing: 'When you think you've lost everything, you find out you can lose a little more.'"

"Not Dark Yet" is arguably the most celebrated song on Time Out of Mind, and is perhaps the clearest example of John Keats' influence on Dylan's writing; it is even possible that "Not Dark Yet" was grown out of Keats' own work. In his book, Dylan's Visions of Sin, Christopher Ricks, a Warren Professor of the Humanities, draws parallels between "Not Dark Yet" and the Keats poem Ode to a Nightingale. Broken down line for line, "similar turns of phrase, figures of speech, [and] felicities of rhyming" can be found throughout "Not Dark Yet" and the Ode. Ricks also argues that "there is a strong affinity with Keats in the way that in the song night colours, darkens, the whole atmosphere while never being spoken of," just as Keats used winter to color and darken the atmosphere in another poem he wrote, To Autumn. "Dylan's refrain or burden is 'It's not dark yet, but it's getting there.' He bears it and bares it beautifully, with exquisite precision of voice, dry humour, and resilience, all these in the cause of fortitude at life's going to be brought to an end by death."

The longest composition ever recorded by Dylan, the 16-minute "Highlands" took its central motif ("My heart's in the highlands,") from a chorus in a stall ballad called "The Strong Walls of Derry." Jim Dickinson later recalled Dylan "leaning over the equipment case working on the lyrics...with a pencil."