Some of my favorite artists are even older than me and have been putting out records for a very long time. I was still a kid when I started following their adult careers, so that’s 50 years or so of releasing albums for the ones that survived. Even after my musical heroes pass, their record labels often continue to put out new compilations and archived recordings. Their extensive catalogs, despite how deeply I admire their work, are too damn unwieldy to reasonably expect that I’ll keep listening to everything they put out and still get anything else done in my life. Thankfully, all of these great musicians have a small handful of albums I go back to when I want to experience their particular magic. In this new series, I’m going to be narrowing down these prodigious outputs to my ten favorites, which is about how many stay in my active rotation with each of them. These aren’t intended to be “best of” lists, that’s ludicrously subjective with such groundbreaking and creative work. They’re personal big-picture favorites, the ones I go back to in my dotage after investigating everything for the previous four or five decades. Anything officially released in the U.S. is fair game, greatest hits and live albums will definitely appear on most of my lists.
I’m starting with Mr. Dylan because he’s one of the faces on my personal music Mount Rushmore. As sappy as it sounds, he changed my life, at least my how-I-think-about-creativity life. His work taught me that, in any creative pursuit, rules and expectations are for the audience to worry about, not the artist, and that tomorrow’s work is infinitely more important than yesterday’s. I’m sure he had no intention of teaching my sorry ass anything, but I’m forever grateful.
The Dylan Discography – I’m using Wikipedia’s numbers to get a final count of official releases. In Dylan’s case, that means 39 studio albums, 15 stand-alone live albums, 29 official hits compilations, and 22 box sets, which include his ongoing Bootleg Series. Listing the final ten in order of preference was more difficult than whittling the discography down that far in the first place, but this ranking works for me, and pretty much lines up with how many times I’ve heard each one over the years.
1. Blonde On Blonde (1966) – My first purchase of this one was on black vinyl back in the day, and I played it until that piece of plastic turned white. I sucked every note out of those two LPs until they had nothing left to give except static and some thin, wild, mercury sounds. I would listen through my speakers, with my headphones on, or bring it over to friends’ houses and insist they play it. The words and the sound were so completely new and mesmerizing I couldn’t listen to anything else for months. All I had were questions: Who was this Johanna, and why was she worth having visions of? What was it that one of us must know (sooner or later)? Why was owning a leopard-skin pill-box hat so worthy of the singer’s scorn? How does one steal a post office? I got very few answers over the years, and never cared in the slightest. Blonde on Blonde taught me that the questions can be intensely satisfying on their own.
EARWORM: “Stuck Inside of Mobile with the Memphis Blues Again” – Don’t bother trying to figure out what the fantastic(al) lyrics mean, just dive in and let the “Oh Mama, can this really be the end?” chorus sweep you up again and again. Forget about who the ragman might be. https://open.spotify.com/track/1NYTj6JEw3IOh4ggiBh82h?si=fdae6a41df6f4920
2. Blood on the Tracks (1975) – If you don’t hear this album as Bob’s “divorce” record, as his fellow musicians and his son, Jakob, insist it was (although Bob strongly denies it), what you have is a beautiful, mostly acoustic, album with one of Dylan’s most emotionally sophisticated set of lyrics. I didn’t hear it as a divorce record back in the day because I had no experience in such things, by 1975 I had yet to even experience a broken heart. After my divorce I realized what Bob was writing about wasn’t the heartbreak of an ending relationship at all, but the sense of the world becoming something other than what it had been, what you had relied on it being. Feeling uprooted and looking backward and forward because your now is so undefined. These days I believe Jakob is right and appreciate the album's depth even more.
EARWORM: “Tangled Up in Blue” – Lovely yet dense lyrics about feeling uprooted in this life, over an irresistible acoustic guitar line. One of his most astonishing songs.
3. Desire (1976) – After what must have been some sort of catharsis with Blood on the Tracks (including its massive commercial and critical success), Bob shook everything up. Again. There’s an attractive freedom to this record, a kind of gypsy wildness that never fails to pull me right in, even when he’s singing an eleven-minute dirge about a New York mobster. Dylan was walking a high wire with no net on this one, I feel that delicious tension every time I play it.
EARWORM: “One More Cup of Coffee (Valley Below)” – A brilliant use of the album’s two secret weapons; a gorgeous duet with Emmylou Harris, backed by Scarlet Rivera’s bewitching violin.
4. Bob Dylan’s Greatest Hits, Vol. II (1971) – I owned Volume 1, of course, and loved it. Those timeless songs, the trippy Milton Glaser poster that I taped to my wall like everybody else. But in every case the songs hit me harder in the context of their original albums, so I didn’t pull it out much. Volume 2 was put together with Dylan’s song choices, not the record label’s, and the difference is night and day. There are unreleased tracks, a grainy live recording from somewhere, and deep album cuts that are exactly the ones I would have chosen, had he consulted with me. Unlike Volume 1, this one feels personal, more representative of where Bob’s artistic vision was at the time, and plays like yet another essential Dylan album.
EARWORM: “Just Like Tom Thumb’s Blues” – If I had a gun to my head and was forced to choose, my favorite Dylan song. Thankfully, that scenario never happens. Wild, imagistic lyrics describing a trip Bob took to Juarez, Mexico, where the poverty and lawlessness reportedly shook him up. Breathtaking words and rhymes from a career full of them. https://open.spotify.com/track/5QhuzE05Nypw6O3xfSPAVx?si=0bba3f11b7b3400b
5. Before the Flood (1974) – The last time Dylan and The Band had toured together before this one was in 1966, when they got booed most nights during their second, loudly electric, set. I had one of the most famous bootlegs from that tour, the Royal Albert Hall show (which was later correctly identified as being from the Manchester Free Trade Hall), and despite the crowd being pissed off that Dylan was no longer the acoustic protest song troubadour they loved, the music was edgy, exciting, and amphetamine wired, a whole new Dylan sound. That record didn’t prepare me for this one. When Dylan and The Band hit the road again in ’74 they were a loud, aggressive steamroller. Once again, a whole new Dylan sound, this time it’s a previously unheard hard rock approach, tailored to the bigger arenas they were playing. I absolutely love the lack of subtlety and precision on this one. The Band is (brilliantly) playing like a freight train about to fly off the rails at any second, while Bob nearly shouts the words to the nosebleed seats. It’s crazed, exciting rock and roll, and by the end the crowd is ecstatic. I remember reading in Creem magazine at the time that this was either the best or worst live album ever released, the reviewer couldn’t decide. I could, Before the Flood is one of my top two or three favorite live albums ever.
EARWORM: “Like a Rolling Stone” – Either the last or next to last song of the night, depending on which city you saw them in. The crowd reaction was always over-the-top bonkers by the time they got there.
6. Oh Mercy (1989) – By 1989 I had lost faith, and interest, in Dylan’s career. I felt like his fuel rods were spent, his creative engine had run out of gas, his songwriting train had derailed, whatever metaphor for declining artistic relevance you’d care to throw in here works for me. After 1983’s mostly-great Infidels, he had released three sloppy, tossed off albums in a row with less than one album’s worth of decent songs between them. They had been savaged by the critics and sold poorly, so it wasn’t just me feeling like his former brilliance was a thing of the past.
It’s always difficult to tell how Bob sees his work at any given moment, but I’m guessing there was at least some concern about his career and legacy because he took an entirely different approach to Oh Mercy. He wrote a new, truly impressive batch of songs, went down to New Orleans and put himself in the hands of producer/musician to the alternative music stars Daniel Lanois. Lanois’ swampy, moody soundscapes fit Bob’s new songs perfectly, and I, to my great surprise and delight, had a new Dylan album to play incessantly. I was completely invested in following his career again, only to see him release three more hastily-recorded and generally terrible albums right after this one, worse than the three that had preceded it. But this gem kept me going until he and Lanois teamed up again and righted the ship with Time Out of Mind in ’97. Oh Mercy has a favored spot as my oasis-in-the-desert Dylan album.
EARWORM: “Everything is Broken” – The opener, “Political World,” let me know immediately that Bob was back in the game. This song showed me he was still the master of that particular game.
7. Love and Theft (2001) – Love and Theft came three years after the acclaimed Time Out of Mind had fans and critics confidently discussing Dylan’s creative and popular “comeback.” But Bob being Bob, this album was another sharp left turn following a previous success. Dylan stopped using outside producers or studio musicians, his recordings became entirely in-house projects at this point, he and his Never Ending Tour road warriors were gonna handle everything from here on out.
I had the same reaction as everybody else when I threw L&T on the first time – “What the hell happened to Bob’s voice?” It was deeper, raspier, ancient sounding compared to the last record. But as I listened, I realized the same could be said for the songs; they sounded looser, noticeably raspy and ragged around the edges. And they are unquestionably a magnificent batch of songs, even by his own standards. Dylan was obviously feeling inspired by the old, obscure American folk, pop, and acoustic blues songs he and his band were frequently slipping into their concert setlists to confuse the fans. Most of the songs sound like modern echoes of tunes from the old, weird America. Bob’s grittier voice both adds gravitas to the heavier songs and really sells the quips, jokes, and humorous asides that pop up all over the record. Ultimately, it's the odd contrast between Dylan suddenly sounding a decade older, while at the same time unleashing a previously unheard amount of sly wit and corny jokes, which makes Love and Theft sound age-defying, hopeful, and lots of fun.
EARWORM: “Mississippi” – One of his all-time great songs. The measured pace lets you fully appreciate his brilliant lyrics.
8. Highway 61 Revisited (1965) – I was seven when this album was released in 1965, so I wasn’t struck by the lightning bolt that was “Like a Rolling Stone” when it first arrived. I heard it at the time, of course, it was a radio hit, and I was already paying attention to the radio in my parent’s kitchen, but I didn’t have a context to put it in until I started focusing my attention on albums several years later. What keeps the record from a higher spot on this list is where it fits in my personal long view of Dylan’s career. Highway 61 has a few entries on my Dylan All-Time Favorites song list - “Just Like Tom Thumb’s Blues,” “Ballad of a Thin Man,” and “It Takes a Lot to Laugh, It Takes a Train to Cry” - with everything else merely great rather than mind-blowing. I hear Highway 61 at a 56-year distance as a fascinating warm-up for the impending creative explosion of Blonde on Blonde more than as a singular out-of-time masterpiece. But that’s just me, legions of Dylan diehards would disagree. Let ‘em write their own lists.
EARWORM: “Ballad of a Thin Man” – One of Dylan’s most enigmatic and tantalizing songs. The question of who Mr. Jones might be, and what he did to piss Bob off, has endured among Dylanophiles for decades.
9. Shot of Love (1981) – Shot of Love probably shouldn’t be on this list, it’s kind of a mess. By this point I was wondering if the old Bob was gone, forever replaced by the new “born again” Bob, the one suffering from a conversion to a particularly strident and judgmental form of Christianity. It followed the completely unlistenable Saved album, so I had my doubts about ever being a true Dylan acolyte again. But that old-time, secular rock and roll lifestyle was beginning to creep back into Bob’s life. Several of the musicians he recorded these songs with wouldn’t have been the kind of guys looking to include a prayer session into the recording, let’s just say. The ragtag nature of the recording sessions, and the absence of a final layer of spit and polish on the tracks, makes Shot of Love a welcome dose of loose, fiery rock and roll and emotionally convincing ballads. Despite the obvious beginning of a transition back to the secular world, Shot of Love also includes two of his best “Christian” songs – the noticeably defensive “Property of Jesus” and the breathtaking “Every Grain of Sand.” And despite (or because of) the album’s confused messaging and ramshackle musicianship, every song on Shot of Love is one I truly enjoy to this day. Still semi-born-again lyrically, it’s the sound of Dylan investigating the broader, secular world again, a shot of salvation I welcomed at the time.
EARWORM: “Every Grain of Sand” – Because if you’ve never heard it, you should. The closest Bob ever got to converting me.
10. Infidels (1983) – The follow-up to Shot of Love opens with “Jokerman,” one of Dylan’s greatest songs and reason enough for the album to make this list. Bob took more care with Infidels and crafted the final transitional step from preaching about sin and salvation to singing about more personal takes on love, loss, and the bigger world outside again. He made the record with Dire Straits’ Mark Knopfler because he wanted to work with somebody who knew the modern recording studio better than he did and hired the superstar Jamaican rhythm section of Sly and Robbie to provide a subtle reggae lilt to a handful of songs. Bringing in ex-Rolling Stone Mick Taylor to play some guitar didn’t hurt either. The results sound rich and detailed, melodic, and just plain marvelous. Dylan sings with both power and a long-abandoned romantic subtlety. I can play and enjoy this one every time simply because of the way it sounds. But unlike Slow Train Coming, Bob’s first “born again” record, which I give a pass because the production is so impressive, I can also focus on Infidel’s lyrics with great pleasure. “Sweetheart Like You,” “License to Kill,” and the Rastafari-influenced (thanks Sly and Robbie) “I and I” seem like his real “rebirth” to my ears.
EARWORM: “Jokerman” – One of the greatest album openers in pop music history. The reason I dropped the needle on Infidels so damn many times.
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