Comparing Bob Dylan albums is a difficult task, in large part because, during his career, the man has often transformed so radically in terms of his music and message. Many times he’s been counted out, only to resurface even stronger. Even now, six years removed from his last album of original material, one gets the impression that he is only marshaling his forces for another incredible run of new music. And even if he isn’t, he has already given us so much amazing material that picking ten albums that separate themselves from the rest of his discography is perilously difficult. But we’ll give it a shot.
10. Desire (1976)
Dylan received songwriting assistance from theater veteran Jacques Levy on this release, thereby continuing his mid-career hot streak. The two men settled, for the most part, on a batch of story-songs, some inspired by the news (“Hurricane” and “Joey”); some quasi-autobiographical then spun through a surreal blender (“One More Cup of Coffee” and “Isis”). Scarlet Rivera’s gypsy violin proves just the right accompaniment for these rambling tales as Dylan closes out the album with “Black Diamond Bay,” an epic fake-out, and “Sara,” a tune so real it’s painful.
9. Slow Train Coming (1979)
Forget the subject matter and concentrate on the music for a minute: With Producer Jerry Wexler, ace guitarist Mark Knopfler, and several Muscle Shoals pros lending their expertise, this album features grooves that are some of the sultriest of Dylan’s career. This sexy sound was appropriate because Dylan had been seduced himself by the Christian faith. “Slow Train” promises Armageddon but does so funkily, while “Gotta Serve Somebody” is a comical explanation of his conversion. “I Believe in You,” “Precious Angel,” and “When He Returns” are all as vulnerable as the man ever sounded. Honestly, the overall effect is touching no matter what you believe.
8. Oh Mercy (1989)
Dylan in the ‘80s wasn’t nearly as bad as it’s sometimes mythologized to be, but there is no doubt that he needed some sort of triumph when he hooked up with producer Daniel Lanois at decade’s end. If nothing else, Lanois brought a coherent moodiness to this album, while Dylan responded with his most consistent set of songs in a decade. Highlights: “Ring Them Bells,” as empathetic as any of the protest material from the early ‘60s; “Man in the Long Black Coat,” so well-executed you can practically smell the evil; and “Shooting Star,” wistful, moonlit, and sweetly heartbroken.
7. The Times They Are A-Changin’ (1964)
Dylan first flexed his songwriting muscle on 1963’s The Freewheelin’ Bob Dylan, but the following year’s release was a more complete triumph. It is hard to fathom that this was a 22-year-old kid writing lyrics of such depth and wisdom. The title track is eternally relevant, “With God on Our Side” speaks eloquently of war’s hypocrisy, and “The Lonesome Death of Hattie Carroll” is a summarizing argument as good as any high-class lawyer could hope to give. Throw in more personal gems like the bereft breakup ballad “Boots of Spanish Leather” and the closing kiss-off “Restless Farewell,” and you have Dylan’s first masterpiece.
6. Time Out of Mind (1997)
When Dylan’s 30th-anniversary concert was held in 1992, it had the feel of a retirement party; surely, the man was out of comebacks. Fooled you. After recharging his batteries with a pair of excellent folk song collections, Dylan reconnected with Lanois, whose production casts a thick pall on the proceedings. Meanwhile, Dylan inhabits the character of a lonely wanderer with such world-weary perfection that he actually convinced many listeners that he wrote the songs while dying. (In fact, the serious infection that very nearly felled him came after the album was in the can.)
5. The Basement Tapes (1975)
Purists complain that The Band songs here weren’t actually part of the legendary Woodstock sessions with Dylan that birthed rock’s first great bootleg. But they are of a piece with the spirit of those recordings and give you even more greatness for your money, so why quibble? As for Dylan, his looseness on songs like “Million Dollar Bash” and “Yea, Heavy and a Bottle of Bread” was revelatory. And that didn’t stop him, with the doleful harmonies of Rick Danko and Richard Manuel seconding his emotions, from also plumbing bottomless depths of sorrow on “Tears of Rage” or conjuring ominous portent on “This Wheel’s on Fire.”
4. Highway 61 Revisited (1965)
After going partially electric earlier in the year on Bringing It All Back Home, Dylan went all-in with a country-blues hybrid sound that was just shy of out of control yet somehow made room for his torrential lyrical downpour. The opening drum crack on “Like a Rolling Stone” heralds one of the great album-openers of all time. “Tombstone Blues” and the title track are fast, funny, and furious; “Ballad of a Thin Man” is an epic takedown; and “Desolation Row” created an entire world that you always want to visit even if you don’t want to live there.
3. Love and Theft (2001)
Although Time Out of a Mind started the comeback, it is largely separate from what came after. “Love and Theft” began a stretch where Dylan produced his albums himself (under his Jack Frost pseudonym) and hooked up with intuitive session players to create music that alternated between barreling blues and twilight ballads, with a unifying characteristic of rootsy authenticity. Dylan also mixed the desolate sadness of the preceding album with many more moods, including flashes of mischievous humor and fierce menace. You can make it a legitimate case for it being his finest ever album some 40 years into his career. Who else does that?
2. Blood on the Tracks (1975)
Dylan swears that it wasn’t an album about his deteriorating marriage. No matter, because listeners have utilized it as their go-to LP when their own relationships are fracturing ever since its release. So many breakup albums released in its wake have been dour and one-sided; Blood on the Tracks finds room for moments of joy, while the narrator bravely owns up to his own part in the debacle: “We’re idiots, babe,” Dylan sings at the end of “Idiot Wind.” Just for good measure, Dylan adds one of the best story songs of all time — “Lily, Rosemary and the Jack of Hearts” — to throw us all off the scent.
1. Blonde on Blonde (1966)
The Dylan faithful diverge about his greatest album, but it’s hard to argue against this behemoth. The music is more refined than you might remember it; for every raucous blues, there is an elegant weeper right alongside it. Dylan’s concerns are largely confined to his inner circle, whether he is angry with them (“Leopard-Skin Pill-Box Hat”), fawning over them (“I Want You”), or missing them (“Visions of Johanna.”) The side-long closer “Sad-Eyed Lady of the Lowlands” is both the apex of his wordy eloquence and his springboard away from it in the albums to come.
Photo of Bob DYLAN; performing live onstage at the benefit for ousted Chileans: Felt Forum, New York (Photo by Steve Morley/Redferns/Getty Images)