Icon: Bob Dylan

How loose could Dylan get? Loose enough to kick off rock's first double-LP with a stoned and staggering party anthem, played by the perplexed Nashville session cats with whom he cut most of it. (The album's front-cover photo is a little out of focus, and there's a certain smoked-up blurriness to most of the songs, too.) How tight could he get? Tight enough to end it with the spellbinding epic "Sad-Eyed Lady of the Lowlands," which his admirers are still unpacking. The real joy of Blonde on Blonde, though, is that it's hard to tell its meticulously crafted jewels (and binoculars) from its casually thrown-together mules — most of its highlights, like the seething blues "Leopard-Skin Pill-Box Hat," seem to have accidentally stumbled onto their enduring power. Dylan's loopy free associations aren't just a tic, they're the centerpiece of his art. Anyone else would've called the jolly breakup tune here "You Go Your Way and I Go Mine" without the "Most Likely," which isn't even in the lyrics; anyone else would've thought twice about throwing in an apropos-of-nothing bridge involving a stilt-walking judge; anybody else in 1966 would have, you know, sung it, instead of magisterially drawling the lyrics like a drunken accusation. But Dylan wasn't like anybody else, and nearly every wild, counter-intuitive gesture he made on this sprawling album was a Zen arrow hitting a bullseye.

Beneath all that bombastic Vegas-style production (saxophones! backup chicks!), there are some spectacular and expansive songs here — Dylan reeling off verse after verse of half-mystical, half-earthbound visions of travel and transcendence like "Changing of the Guards." There's also a curiously nasty, dominant streak of sexuality, especially on the seething blues "New Pony."

By 1979, Dylan's fans were used to his album-by-album transformations, but his embrace of born-again Christianity took a lot of them by surprise. So did the hectoring fire-and-brimstone tone he took on his new songs — the master of ambiguity was now spitting pronouncements like "ya either got faith or ya got unbelief and there ain't no neutral ground" — as well as his refusal to play any of his old secular material live. Still, he sugarcoated his Bible-thumping with impressive music: production by soul veteran Jerry Wexler, lead guitar from Dire Straits' Mark Knopfler, a Grammy-winning single in "Gotta Serve Somebody," and an adorable children's song called "Man Gave Names to All the Animals."

Dylan's second Christian album retraces rock's path through R&B to gospel — he's got a handful of soul veterans in the band, and "Solid Rock" grooves like nothing else he's recorded. The lyrics are undiluted born-again dogma, which shocked fans who were used to Dylan's don't-follow-leaders irreverence. But a lot of these songs make more musical sense if you consider them as a Dylanization of the black gospel of the '40s and '50s.

"Love is so simple, to quote a phrase," Dylan snaps. But breakups aren't so simple, and there's no other record that captures the blinding, complicated pain of a dissolving relationship like this. Full of rage and longing and knotty memories, these are mutable songs — they're a matched set (all of them were written in the same open tuning, and half of them end each verse with a refrain), but he famously rewrote and re-recorded half of them with a pick-up band a few weeks before the album came out. "Tangled Up in Blue," a strong candidate for his greatest song, kept changing shape in concert for decades, sometimes with new lyrics and sometimes simply by virtue of what words Dylan emphasized in each performance. The deeper you go into the emotional labyrinths of these prismatic narratives and aching, painterly observations, the deeper they get. Sometimes their insights are direct, as in "You're Gonna Make Me Lonesome When You Go," a perfect love song with a permanent leavetaking built into it; sometimes they're oblique, as in "Lily, Rosemary and the Jack of Hearts," a nine-minute Western drama about a sacrifice for love. And sometimes they take the form of naked, blistering pain, especially on the vituperative left-right combination of "You're a Big Girl Now" and "Idiot Wind."

Recorded and released almost immediately after Self-Portrait, this is simply a modest singer-songwriter album — everything on it feels casually tossed off, the band plays with a light touch, and there are some genuinely silly things here, especially the fake hepcat-jazz recitation "If Dogs Run Free." But his natural gifts for rhyme and tune (not to mention his natural oddness) still shine through: "If Not For You" is a fake Tin Pan Alley number that went on to be memorably covered by both George Harrison and Olivia Newton-John. And, for once, Dylan sounds genuinely happy. "The Man In Me" even starts with a "la la la" chorus, and "Time Passes Slowly" and "New Morning" are both paeans to the pleasures of hanging out with a loved one, doing nothing in particular.

After seven years of songwriting silence, Dylan surprised everyone by returning in full glory if "glory" is the right word for songs as doomy as these — and won an Album of the Year Grammy. He'd also finally figured out how to make the ragged husk of his youthful voice dramatically and musically effective. "I'm sick of love," he declares at the outset, and the love that he suggests is already slipping from his memory's trembling clutch is his only consolation here against the ravages of sickness and age. Death hovers around the margins of most of these songs, underscored by Daniel Lanois' spooky production. Dylan's persona is half a ghost already, and his longest song ever, "Highlands," is almost pure desolation, a Samuel Beckett-ish voice talking to itself, trying and failing to interact with the world around it.

A confused album, recorded at a time when Dylan was struggling to figure out how to present his bleak, shuddering new songs in the age of MTV. "Dark Eyes," which is just the singer and his guitar, is a small gem, but a lot of the material creaks under the weight of overly busy arrangements — "When the Night Comes Falling from the Sky" is a bizarre stab at new wave dance music.

Its title swiped from an Eric Lott book about minstrelsy, its music palmed from a smattering of vintage 78s and 45s, a few of its lines appropriated from a biography of a Japanese gangster, this is 100% a late-model Bob Dylan masterpiece. It's a magpie wonder, slyly observing the millions of little thefts and other injustices that make up the American pop, jazz, blues and country traditions he loves so dearly, even as he adds a few to the pile. His voice is shot to hell, which just makes his jump blues and riverside meditations sound sager, and his lyrical persona is a marvelously cranky, funny old guy, chatting on key as much as he sings — on no previous Dylan album would it have been possible to imagine the phrases "2 a.m. booty call" and "Freddie or not, here I come." And what's he singing about this time? Mostly what to do while everyone's waiting for the Apocalypse to arrive — which it effectively does on the album's centerpiece, "High Water (For Charlie Patton)," a brother to Patton's song about the great Mississippi flood of 1927. In the meantime, there's love, of course, and sparing the defeated, and cracking the occasional joke, and returning to the crackling shellac that keeps the moonlight of the past shining.

After a motorcycle accident sidelined him for the Summer of Love, Dylan returned with the least psychedelic album of 1967, a dozen shockingly unfancy songs that take their lyrical visions Bible-style and owe more to Hank Williams than to the Beatles. St. Augustine, Thomas Paine and "Judas Priest" all turn up as characters in these cryptic parables about slavery, law and the vagaries of fate. It's his most austere album, but it might also be his most haunting — and it's got flashes of loony wit, too. "I'll Be Your Baby Tonight" could be addressed to an actual baby: "bring that bottle over here," Dylan croons.

The 20-year-old kid who recorded Dylan's first album was promising as anything — a favorite on the coffeehouse folk circuit, with fleet fingers, an agile if rough-hewn young voice that could navigate a thousand songs he'd learned from dusty old 78s, and a major, major Woody Guthrie fixation. (The two awkward Dylan "originals" are both heavily inspired by Guthrie songs.) Bob Dylan sold poorly at the time, and it doesn't offer the slightest indication of what this particular singer would eventually become, but it's a fun, confident folk record. Listening to it in 1962, you might have thought he could get to be as big as Joan Baez someday.

His songwriting well had run dry, so Dylan recorded an unaccompanied voice-and-guitar album where he went back to his version of basics: the standards and folk tunes he'd internalized in his coffeehouse days, from the Mississippi Sheiks' "Sittin' On Top of the World" to imperishable ballads from Harry Smith's Anthology of American Folk Music.

Another home-recorded solo-acoustic album of folk songs and country blues, all of them thoroughly Dylanized. It's a despairing set of material — the refrain of "Delia" goes "all the friends I ever had are gone" — but Bob's alligator-skin voice crackles with heat, and his guitar playing is his sharpest in decades, especially on Blind Willie McTell's acid-spitting "Broke Down Engine."

The title isn't quite ironic, it's just disapproving. 65-year-old Dylan is settled comfortably into his latest persona, a slim, slick, slightly disreputable old rake who "can't go to Paradise no more/I killed a man back there," and he's drawing direct lines between his own work and an American popular song tradition that ended right around the time he started recording. In practice, that means he's borrowing more freely than ever before from the old-time pop and blues records he loves. "Rollin' and Tumblin'" lifts its arrangement from Muddy Waters' version, "When the Deal Goes Down" cops a Bing Crosby melody, and that's just the beginning — and a number of lines from Confederate poet Henry Timrod, of all people, are sprinkled throughout the album.

Released to tie in with Martin Scorsese's documentary about the early years of Dylan's career--everything up to his 1966 tour — this collection of live performances and alternate takes from the same era doesn't add many titles to his repertoire, aside from two masterful songs from the widely bootlegged 1961 "Minnesota hotel tape." But the electric material on the second disc (which effectively incorporates an alternate Highway 61 Revisited) is mostly worth hearing for Dylanophiles: the plugged-in "Maggie's Farm" that freaked the Newport Folk Festival out, a tougher "Leopard-Skin Pill-Box Hat," a live "Ballad of a Thin Man" that seriously rakes Mr. Jones over the coals.

Back on top of his game after Blood on the Tracks became a hit, Dylan made a very different kind of record. Co-written with theatrical director Jacques Levy, Desire is a series of dramatic scenarios and narratives, some about real people ("Hurricane," which became a radio hit, and "Joey" respectively concern jailed boxer Rubin Carter and gangster Joey Gallo), others fantastical fiction, almost all of them mentioning or set in faraway climes. Finally, Dylan drops all the masks for "Sara," a desperate plea of devotion addressed directly to his wife, with whom his relationship had lately been turbulent; on stage, he also introduced "Isis" as "a song about marriage."

It's an expansive album, whose nine songs average over six minutes long. At a moment when pop music was speeding up and glittering up, Dylan perversely slowed his tempos to a crawl, lingering over every phrase. (Emmylou Harris's backup vocals sweeten his nasal croak on a few songs, especially the mystical Isis-and-Osiris fantasy "Oh, Sister.") He also constructed his arrangements with greater care than usual — the album's most distinctive instrumental voice belongs to violinist Scarlet Rivera, who Dylan had literally picked up off the street. In any case, his precision and contrarianism paid off: Desire became one of Dylan's best-selling studio albums, supported by the Rolling Thunder Revue tour of 1975 and 1976.

Recorded as the soundtrack for a Sam Peckinpah movie, this is mostly straightforward instrumental music in the Western-flick tradition — which isn't what anyone had expected from Dylan's first new album in three years. It's notable mostly for the classic three-chord deathbed ballad "Knockin' on Heaven's Door," subsequently covered by everyone from Guns n' Roses to Dolly Parton.

Think of this slapdash collection as a single for "Brownsville Girl" with a bunch of trivial B-sides, and it's a lot easier to deal with. An eleven-minute epic co-written by playwright Sam Shepard, "Brownsville Girl" (a sideways tribute to Woody Guthrie's "Danville Girl") is a woozy, rambling Western with a heartbroken narrator who's lost his way almost as badly as the singer.

Dylan's collaboration with Was (Not Was) resulted in a very minor album, but one that's full of little treats, especially the chipper eschatological blues "Cat's in the Well." At the time, it was derided for opening with a goof called "Wiggle Wiggle" — was the poet laureate of rock reduced to this? — but, in fact, most of the album's lyrics incorporate cleverly scrambled fragments of nursery rhymes. ("Handy Dandy" is the creepy cousin of Humpty Dumpty.)

The folk scene thought Dylan had betrayed them by "going electric" on the first half of this watershed record and abandoning topical political songs in favor of whatever was on his roiling, restless mind. In fact, he just opened up possibilities for himself — and created folk-rock while he was at it. He's raiding ideas from blues and traditional songs even more deftly than before, and cranking them up until they're as immediate and catchy as the British Invasion pop that had taken over the airwaves in the previous year or so. "Maggie's Farm" is as delicious and resilient a critique of capitalism and its power relations as anyone has ever cooked up; "Subterranean Homesick Blues" pours out of Dylan faster than anyone can parse it. The electric half of the album is also funnier than history tends to remember — its last three songs are straight-up comedy. Every lyric on the album is packed with explosive little bon mots: "you don't need a weatherman to know which way the wind blows," "you are a walking antique," "skippin' reels of rhyme," "the highway is for gamblers." And the four imagistic wonders that constitute the original LP's second side were some of the first successful fusions of their era's poetry with pop music. What's "Mr. Tambourine Man" about? Anything you want it to be, pretty much, but mostly the delirious power of Dylan's language.

Recorded over the course of a year, Dylan's second album instantly transformed the scruffy young singer-songwriter from a promising young Woody Guthrie fan to the undisputed king of the folk revival, an alpha tiger with his claws bared and a wide, red-fanged grin. "Blowin' in the Wind" alone would have made his reputation — Peter, Paul and Mary had a gigantic hit with their cover around the same time as Freewheelin' was released, and all of a sudden, every singer in America wanted an acoustic guitar, a harmonica and an encyclopedic command of poetry and the folk repertoire. (Only two of those were available in stores.) But the album never lets up. It's a virtuosic parade of tender and bitter love songs and political screeds with a thousand years of momentum behind them. "Don't Think Twice, It's All Right" is still a shocking kiss-off, and features impossibly virtuosic guitar picking to boot; "A Hard Rain's a-Gonna Fall" mutates the traditional ballad "Lord Randal" into a poetic, prophetic vision of nuclear apocalypse; "Masters of War" confronts the "big guns" of the military-industrial complex with an unforgettable indictment. "Corrina, Corrina" is the only full-on "folk song" here, but the entire record is the sound of Dylan dragging the backward-looking establishment of the folk tradition into the New York City of 1963.

The rock 'n' roll bootleg album was actually invented for Dylan — the first documented bootleg LP was 1969's Great White Wonder, a collection of his unreleased material. That's because, well into the '80s, he recorded much more than he released — and was singularly perverse about what he released and shelved. His ongoing archive-raiding series began with this triple-CD set of outtakes, live tracks, demos and false starts down un-followed roads. The unreleased tracks from his acoustic era are mostly second-tier stuff and odd stabs at comedy like "Talkin' Hava Negeilah Blues," although a few songs like "Eternal Circle" still put most of his contemporaries to shame. (There's also a long, rambling poem called "Last Thoughts on Woody Guthrie," which is what it sounds like.) But the set goes electric with a bang — a raucous Beatles pastiche called "If You Gotta Go, Go Now" — and from there on out it's at least interesting and at best essential, encompassing a waltz-time stab at "Like a Rolling Stone," the feverish Blonde on Blonde outtake "She's Your Lover Now," and some harrowing songs from the original, scrapped version of Blood on the Tracks. The last ten tracks, in particular, would've been his best album of the '80s, salvaging lost masterpieces like "Blind Willie McTell" and "Series of Dreams" from the scrap-bin.

The granddaddy of all boxed-set retrospectives (named after a blues reissue label!) is a magnificent overview of the first 25 years of Dylan's career, and its smartest move is avoiding chronology in favor of a thematic exploration of Dylan's work. It starts like a seduction, with a string of subdued come-ons, then displays the songwriter's plumage: protest songs, rock 'n' roll, mystical visions, sprays of venom, and more, culminating with a set of hymns and meditations that contextualizes the explicitly Christian songs he was writing around 1980 in a personal tradition that encompasses "All Along the Watchtower" and "Knockin' On Heaven's Door."

More than a third of Biograph's tracks hadn't appeared on an album before, including some astonishing stuff — Dylan's first electric recording ("Mixed-Up Confusion," from 1962!), the early-'80s epic "Caribbean Wind," the sneering ditch-your-boyfriend rant "Can You Please Crawl Out Your Window?," and a slew of live tracks, most notably a ferally intense "Isis" from 1975. But even the box's familiar favorites (almost all of Greatest Hits appears here) are alchemically transformed by their context —"I Want You," for instance, seems like a different song between two other visions of lust, 1965's Beatles/Stones homage "I Wanna Be Your Lover" and 1981's fervent "Heart of Mine." Not many albums can serve both as an introduction for the curious and a revelation for the faithful, but this set pulls it off.

Dylan is nothing if not a contrarian, and his reaction to the late-'60s audience that expected visionary rock poetry from him was to become a lightweight country singer with moon-June rhymes and a clear, crooning tenor voice. There's even an acoustic duet with Johnny Cash up front as a sort of "who, me? A rock star? Surely you must be thinking of someone else" gesture. The punch line is that Dylan's kind of terrific at lightweight country: "Lay, Lady, Lay" became one of his biggest hits, and a few other tracks, especially "I Threw It All Away," achieve the kind of profound simplicity he's always sought out in other people's songs.

A famously — and deliberately — dreadful album: Dylan hurling the contents of his junk drawer at Dylanologists to throw them off his trail. It's a mess of out-of-tune covers, schlocky string arrangements, half-remembered folk tunes and some middling live tracks from 1969's Isle of Wight festival. "Copper Kettle" isn't bad, though.

The third and last of Dylan's overtly Christian albums is also the most peculiar. Winnowed down from dozens of recordings, it's got a handful of extraordinary songs — especially the exquisite, prayerful ballad "Every Grain of Sand" and a raving rocker called "The Groom's Still Waiting at the Altar" — sprinkled among finger-pointing, asthmatic stomps.

Dylan was way out of his element in the late '80s, and his 25th studio album was awkwardly tacked together from five years' worth of sessions with dozens of musicians (including Jerry Garcia, Full Force and the Sex Pistols' Steve Jones), and heavy on the covers and co-writes. He only sounds fully present on his cover of the Stanley Brothers' alienation album "Rank Strangers."

Dylan's performance at the Free Trade Hall in Manchester England on May 17, 1966, may be the single most famous concert in the history of rock — bootleg editions of it circulated from the early '70s until this version saw legitimate release in 1998, and it lives up to its reputation. In those days, it was still a huge deal that the former champion of folk music was playing with a rock band (the Hawks, who later became the Band); people actually came to the shows to yell at him for selling out.

To be fair, Dylan was a lot more invested in charging ahead than in pleasing his old fans. The polite, draggy acoustic set on this set's first disc has nothing earlier than Bringing It All Back Home, and a couple of songs from Blonde on Blonde, which had come out literally the previous day. But then he comes out again with the Hawks, audibly out of his head, howling a speedfreak rocker called "Tell Me, Momma" whose lyrics are more phonemes than words, and the place goes nuts. He turns a couple of old acoustic favorites into electric blitzkriegs; he howls like he's discovered punk rock a decade early. Eventually, a heckler calls him "Judas," Dylan responds "I don't believe you!... You're a liar!," the band breaks into a scorched-earth rendition of "Like a Rolling Stone," and everybody goes home shell-shocked.

A document of the 1976 leg of the Rolling Thunder tour, Hard Rain debuted yet another side of Bob Dylan: an entertainer with murder in his eyes, playing good-time rock 'n' roll with a horse's head hidden inside it. Released to coincide with a live TV special, it's the slickest-sounding album he'd ever made, bubbling arena rock with quicksilver glam-rock guitars (the band featured five guitarists, including T-Bone Burnett and Mick Ronson). The repertoire, though, focuses on the vituperative resignations and half-contemptuous love songs in his catalogue, and his performances twist them into something even darker than their original form — "Idiot Wind," in particular, becomes a ten-minute thunderstorm of bitter rage.

Shortly before the release of Desire, Dylan went out on a legendary tour with a gaggle of old friends (including Joan Baez, who duets with him here) and a sprawling band called Guam that featured violinist Scarlet Rivera and David Bowie's former guitarist Mick Ronson. He recasts his '60s standards as bulked-up, rafter-reaching glam rock with grand theatrical flourishes; amazingly, most of them survive the transition just fine. And his newest, more narrative songs crackle and sparkle, especially "Isis," a wild-eyed fable about marriage that Dylan declaims with passionate fervor, and "Hurricane," an eight-minute harangue on behalf of jailed boxer Rubin Carter.

The last hurrah of Dylan the protest singer. The audience at this Halloween, 1964 show ("I have my Bob Dylan mask on," he quips) knows and loves and is totally down with the political lyrics from his last few records, and he knows how to flirt with them — when he blows the beginning of "I Don't Believe You," his request for them to remind him how it goes draws a big laugh. Still, he's clearly more interested in playing his new, unrecorded, more visionary stuff (this was the public debut of "It's Alright, Ma"). Joan Baez, who wouldn't dare to snark up her singing the way Dylan does, joins him for four rapturously received duets.