Bob Dylan’s carved out a legacy over six decades and 40 studio albums, cementing himself as a songwriting colossus whose words cut straight to the bone. Whether he’s growling them himself, handing them off to other voices, or crafting them for someone else, his lyrics dig deep—stirring the gut and rattling the mind. Built on looping verses and fueled by a poet’s fire, his catalog sprawls across politics, heartbreak, and the edges of the unknown.
You can trace his restless evolution through two gems: “Farewell Angelina” and “Angelina,” both unearthed on The Bootleg Series Volumes 1–3: Rare & Unreleased in 1991. “Farewell Angelina” came first, penned for his 1965 record Bringing It All Back Home, but he passed it to Joan Baez—his flame at the time—for her own album of the same name. “Angelina,” though, was a later beast, born for 1981’s Shot of Love only to get sidelined, left to simmer in the vaults until the bootleg drop.
“Farewell Angelina” rides the raw, folk backbone of Dylan’s ‘60s sound, all acoustic strums and open road vibes. But “Angelina” swerves hard into something bigger, darker—teaming up with Jimmy Iovine, Dylan conjures a ghostly piano that drifts like fog, wrapping the song in a hollow, eerie glow that amplifies its weight.
The lyrics hit like a fever dream, dripping with holy dread and wild visions, making “Angelina” one of Dylan’s most cryptic puzzles. Doom seeps through every line, with Biblical echoes painting a sky ready to crack. He summons Revelation 6:8—“I can see the unknown rider, I can see the pale white horse”—death’s shadow galloping free. Then there’s “I see pieces of men marching, trying to take Heaven by force,” a jagged snapshot of power gone mad, greed clawing at the divine.
Dylan’s narrator stumbles through a wasteland—“Blood dryin’ in my yellow hair as I go from shore to shore”—a line that feels like someone else’s story, not the dark-haired bard we know. It’s a trek through despair, a soul grasping for something solid in a world tumbling apart. The end comes brutal and vivid: “Beat a path of retreat up them spiral staircases, pass the tree of smoke, pass the angel with four faces, begging God for mercy and weepin’ and moanin’ in unholy places.” It’s a descent into a gothic abyss, stark and unsparing.
Through it all, he softens the blow with “Oh Angelina,” a whisper of a refrain that floats tender and fragile against the storm of words. That sparse piano and those haunting images crack open Dylan’s shadowy side—a gothic streak that’s always lurked in his tunes but rarely cuts this deep. “Angelina” might be his bleakest howl, a masterpiece too heavy for Shot of Love, or maybe just too strange. Whatever kept it off the record, it stands alone—chilling, untamed, and unforgettable.
