Essentials: The Top ’80s Bob Dylan Songs

Lean in close, don’t tell anyone, but the ’80s is my favourite Bob Dylan decade. How can this be, you ask? (Or is that me asking myself?) This generally accepted decade of decline, which included scattershot albums as bleak as ‘Down in the Groove,’ where the slim number of originals included songs like ‘Ugliest Girl in the World.’ Well, as Tom Waits once said, Bob Dylan is a planet to be explored, and I have spent many years exploring the well-trod terrains of his peak periods: the monument valley of the ’60s, the sweeping western vistas of the ’70s, and the more recent fertile fields of his comeback decades. However, the ’80s, as parched as it was, contained many unique shimmering jewels amidst its often barren landscape.

Coming off the back of his Christian trilogy, Dylan appeared at war with himself, or at least the image of his former self. Strained vocals, hairspray, under-cooked and critically savaged albums, featuring backup singers, children’s choirs, ardent attempts to remain contemporary, and confounding decisions, including ditching some of his best songs of the period off his albums. Indeed, four of these ten were excluded from their intended albums. As if evidence that Dylan’s greatest conflict was often with himself.

In his 2004 memoir ‘Chronicles,’ Dylan says of the time, “I felt done for, an empty burned-out wreck. Too much static in my head and I couldn’t dump the stuff … My own songs had become strangers to me…” However, among that wreckage are wonders. A new voice, a rambunctious stew of rock and roll and reggae rhythms matched with a merging of apocalyptic biblical imagery and hard-boiled realism. The best showcase the singularity of his talent, that neither changing times nor his own missteps could suppress.

10. ‘Caribbean Wind‘ (1981)

Sometime between 1982 and 1983, Dylan disappeared off the map, spending time sailing the Caribbean on his custom-built yacht, ‘The Morning Pearl.’ The languid rhythms and haunting melodies of ‘Caribbean Wind‘ breathe with mystery. The oblique lyrics are filled with yearning and striving, a song of rebirth envisioned from the claustrophobic heat of a hotel room. Multiple versions were attempted, but none made it to a final album. This slower version, released as part of the recent archival ‘Bootleg Series,’ reflects weariness, as if Dylan could feel the mercury of it slipping from his fingers. It touches upon much of where Dylan was at this time—spiritually torn and adrift in a wavering decade.

09. ‘Tight Connection to My Heart‘ (1985) (Cover version)

Upbeat and wry. Dylan intertextuality stirs in a mix of Bogart film noir lines that give a hard-boiled wit. The released version was swamped in synths that plagued much of ‘Empire Burlesque.’ This reimagined version comes from the recent Conor McPherson musical ‘Girl from the North Country,’ which draws out the yearning.

08. ‘Most of the Time‘ (1989)

Dylan at his most beguiling. A song from another time and place. ’80s Dylan couldn’t do many of the things ’60s Dylan could, but he was capable of these new low moods of sanguine and sorcery. A dim glimpse into the blurred lines of human relationships. A beating blue heart of regret. As the decade ended, the Daniel Lanois-produced ‘Oh Mercy‘ foreshadowed directions Dylan would travel next.

07. ‘Dark Eyes‘ (1985)

‘Empire Burlesque‘ was a synth-laden attempt to contemporize Dylan’s sound, but it ends with this acoustic midnight hymn. An Irish folk melody which Dylan delivers with a beautifully crafted vocal filled with dark existential mystery. “A million faces at my feet and all I see are dark eyes.” Swashbuckling romanticism, Civil War doom, shadow figures around the battlefield campfire. The inner visions of a man who’s seen too clearly and too much.

06. ‘Every Grain of Sand‘ (1981)

One of Dylan’s most careful and cultivated songs of the decade and still a regular in concert performances. Dylan channels William Blake to curate this gentle masterpiece of heaven and hell philosophy.

05. ‘Foot of Pride‘ (1983)

Savvy and cutthroat, a pulsing stripped-back exposition of sinners, saints, and all those in between. A speaker’s corner diatribe; spouting visions and taking names. Paired down instrumentation and Dylan at his mercurial best, mouthing mistrust.

04. ‘Blind Willie McTell‘ (1983)

A widely accepted latter-day Dylan masterpiece that was cut from 1984’s ‘Infidels.’ Dylan peers into the wounded heart of America, the scars of slavery, the smoke and shadows of past crimes. Heavy with portent, the smell of magnolia, rich southern night atmosphere. Regret, fear, and the corruption of innocence. Dylan peers into the human heart and sees only darkness.

03. ‘Jokerman‘ (1983)

Dylan is back in the Caribbean. The world is raging. The horizon is heavy with storms. The skies are slippery grey. The future is unwritten and filled with uncertainty. Island shadows, ghost dreams, power struggles, the prince of darkness, the hunted and haunted. Soulfully underwritten Sly and Robbie rhythms. Dylan the poet in full embodiment of his powers.

02. ‘Brownsville Girl‘ (1986)

An Americana dream, pulp novel, road movie, western 13-minute masterpiece. ‘Badlands‘ meets ‘High Noon.’ The torn fragments of a thousand roadside motel paperbacks. A film with the reels in the wrong order. The shattered fragments of a modern fable. Co-written by playwright Sam Shepard, this is a sweeping, overwrought theatrical extravaganza.

01. ‘Angelina’ (1981)

Swirling and imagistic, an exquisite, fevered, summer night dream. The shattered fragments of a thousand images of sin, lust, violence, and rage. The biblical imagery erupts into a tortuous exposition of raging longing. Dylan, however, never made peace with it. It never found an album home until the ‘Bootleg Series,’ and he never unearthed it in concert.