I didn’t grow up listening to Bob Dylan. My house was a Beatles house. I knew most of the Beatles choruses by heart. But Dylan? I couldn’t have told you any of the names of his songs until my senior year of high school. By that time, I had begun listening to a lot of the pop classics. When I got to Dylan, I was so confused. How did a guy with this voice get to be considered the Voice of a Generation?

If Dylan’s unorthodox voice threw me off at first, it didn’t take long for me to fall in love with his originality. As strange as his voice is, there’s no arguing Dylan’s ability to craft a tune or write a lyric. Pretty soon, that one-of-a-kind, reedy voice came to hold a special kind of beauty to me. After some time exploring his catalog of albums, he became one of my favorite artists.

Listening to any artist’s entire discography can be exhausting and tedious, but Dylan had so many different phases and personalities over the years that each new wave felt like discovering a new artist. From all of his 36 studio albums, I picked the top 12. Why 12? I don’t know. It’s a third of 36. Seemed good.

The Top 12 Bob Dylan Albums


12. Down in the Groove (1988): The common refrain is that the ‘80s were a lost decade for Dylan. He got caught up in a born-again Christian fever and his creativity dipped- or so they say. There’s no question that the genius of his ‘60s and ‘70s albums didn’t surface in the ‘80s, but in retrospect it seems like Dylan’s initial spate of faith-focused albums turned critics off and they largely ignored the rest of the decade’s output. Only Infidels (1983) and Empire Burlesque (1985) get any love, and it’s muted love at that. But I prefer two other albums: Shot of Love (1981, see below) and this one, a 10-track diamond in the rough that has perhaps the purest, least-dated music of Dylan’s 1980s. Groove also has two of his best songs of the decade, the punchy “Silvio” and the soulful “Shenandoah”.


11. Modern Times (2006): As the third album of Dylan’s late-career renaissance, following Time Out of Mind (1997) and Love and Theft (2001, see below), it was understandable to expect a dip in quality. After all, Dylan had silenced his critics with two works that seemed to erase the bad will he built up in the 1980s. Most artists don’t even have one good record after 30 years making music, let alone two. Was three too much to expect? Turns out it wasn’t, as Modern Times sees Dylan at the top of his (admittedly old) game, turning out 10 great folk songs that were interestingly focused on the future. Dylan is almost defiant in his hope for a better life, a life without romantic worries in “Someday Baby”, a life free of the wickedness of others in “Ain’t Talkin’”.


10. Tempest (2012): Dylan’s last great album, and the one on which it sounds like the Bard’s vocal larynx has finally sprung a leak. If you weren’t turned off by Dylan’s voice before Tempest, this won’t be the one to convince you his songwriting is worth getting past the scratchiness (which makes it all the more humorous that he’s releasing a second Frank Sinatra covers album this year). But after the bland Together Through Life (2009), Tempest was a return to the strong songwriting of Modern Times. This time Dylan doubled down on a blues-rock groove that belied an even more light-hearted take on the world, climaxing with the whimsical last track, “Roll On John”.


9. Shot of Love (1981): This is the best of Dylan’s post-conversion albums. You can see why critics continued to lump this in with the uninspired Slow Train Coming (1979) and Saved (1980). There are some unabashed attempts to proselytize through song, like “Property of Jesus” and “Every Grain of Sand”. And Shot was a further commitment to move away from the introspective folk of Dylan’s early-to-mid-‘70s. In fact, Shot is Dylan’s album with the most soul, from the opening title track’s gospel-inspired backup singers to the old-fashioned spiritual style of “Watered-Down Love”.


8. The Times They Are A-Changin’ (1964): While not as well-remembered as Dylan’s breakthrough, The Freewheelin’ Bob Dylan (1963, see below), Times was arguably crafted to make more of an impact. Freewheelin’ had “Blowin’ in the Wind” and “Masters of War”, but nearly every song on Times was meant to be a protest song, starting with the opening title track that became an anthem for the ‘60s, all the way through “The Lonesome Death of Hattie Carroll”, about the murder of a hotel worker by a rich white man. The songs are less witty than on Freewheelin’ and their styles are more one-note, but Times solidified Dylan’s reputation as the Voice of a Generation.


7. “Love and Theft” (2001): Dylan had already had his big critical comeback in 1997 with Time Out of Mind. But I prefer 2001’s “Love and Theft”. Time was Dylan’s first album of original material in 7 years, and as such was his most personal album in a long time. But “Love and Theft” is a more ambitious album full of story songs, weaving tales of the South and its racial tensions. Album high point “High Water (For Charley Patton)” is a tribute to the esteemed blues pioneer in the guise of a story about the 1927 Mississippi River flood in Louisiana. The closer “Sugar Baby” talks about looking for fulfillment in the era of Prohibition. And “Mississippi”, on an album full of concepts, is one of Dylan’s most personal songs, facing romantic consequences that can’t help but feel inevitable.


6. The Basement Tapes (1975): After Dylan survived a traumatic motorcycle accident in 1967, the backing band on his last tour, the Hawks (who would later become The Band), joined him for one of the most famous collaborations in Americana history. In fact, The Basement Tapes, which weren’t released until seven years had passed, is credited with birthing modern Americana, though that’s a specious claim, since it seems there hasn’t been a decade before or since in which Americana didn’t have a big influence on the current music. Regardless, the combination of Dylan with fellow musical geniuses Robbie Robertson, Rick Danko, and Richard Manuel produced some of the most beautiful and fun music of Dylan’s career, including album standouts “Tears of Rage” and “Crash on the Levee”.


5. The Freewheelin’ Bob Dylan (1963): “Blowin’ in the Wind”, Freewheelin’s opener became the most famous protest song of all time, so it’s easy to forget that it’s a very simple song. All the songs on Freewheelin’ are simple, so much simpler than the brand of folk-rock Dylan became famous for later on in the ‘60s. But the lack of lyrical complexity doesn’t mean a lack of lyrical creativity. “Talkin’ World War III Blues” is one of Dylan’s funniest songs, and “Blowin’” has some of his strongest imagery. And the lack of musical complexity doesn’t mean a lack of musical beauty. “A Hard Rain’s A-Gonna Fall” finds its home in a mournful yodel, and the way the chorus builds to its resigned conclusion in “Don’t Think Twice, It’s All Right” is one of Dylan’s better compositions.


4. Highway 61 Revisited (1965): It’s tempting to put Highway 61 Revisited higher on this list on the strength of “Like a Rolling Stone” alone, but the albums ahead of it are there for a reason. This was the album where Dylan “went electric”. To our modern ears, there might not be much of a difference between Highway and its predecessor, Bringing It All Back Home (1965, see below), but so much of Highway is treading new ground. The whistles and slide guitar on the title track are just the most obvious wrinkles Dylan threw into the album’s mix. “Ballad of a Thin Man” and “Desolation Row” are perhaps the most indicative of Dylan’s new direction, the former for its heavy dependence on the organ (foreshadowing Dylan’s collaboration with The Band) and the latter for its 11-minute stream-of-consciousness poetry.


3. Bringing It All Back Home (1965): Album opener “Subterranean Homesick Blues” (which some have said is the first rap song- some have said it, not me!) and “Maggie’s Farm”, while still conforming to Dylan’s established folk structure, are subtle hints at the direction Dylan was about to go. He was beginning to get bored of following the same patterns on song after song, and Bringing is the first step towards his more avant-garde hit albums Highway and Blonde on Blonde (1966, see below). Released the same year as Highway, I prefer Bringing, because though it’s longer, the songwriting is stronger across the board, including “Mr. Tambourine Man” and the underrated “It’s Alright, Ma (I’m Only Bleeding)”.


2. Blonde on Blonde (1966): The best of Dylan’s ‘60s albums is also the longest, which should work against it, but there are just so many great songs on this record. It starts off with his weirdest song to date, “Rainy Day Women #12 & 35”, which riffs on the folk community’s overblown reaction to his new direction using a pot pun. Then there’s a 6-song run, starting with the effortlessly beautiful “Visions of Johanna” and ending with the spiteful “Just Like a Woman”, that is simply unparalleled in pop music. The final song is another 11-minute epic along the lines of “Desolation Row” called “Sad-Eyed Lady of the Lowlands”, but this one was a love song, an ode to Dylan’s new wife, and it’s Dylan at his most direct and most tender. Recorded in Nashville with session musicians, Blonde on Blonde finds the newly married Dylan at his peak, a point that he wouldn’t return to until that new marriage reached a point of turmoil 9 years later.


1. Blood on the Tracks (1975): The breakup album is a well-worn trope in the pop music world, and we may have Dylan to thank for that. Though his relationship with his wife wasn’t ending, they were estranged during Blood’s recording. Dylan has claimed Blood wasn’t a personal album; bullshit. This is one of the most achingly painful albums of all time, at some points full of grief and at others full to bursting of anger. “Idiot Wind” is the best example of the latter, as the title refers to the air coming out of his lover’s mouth. The best example of the former is the opening track, “Tangled Up in Blue”. I’ll write more about this song next week, but it sets the tone for the whole album, communicating with precision the complex and inescapable grief that comes with an ending relationship. I was trying to remember if Blood on the Tracks helped me cope with any of my own dissolving relationships in the past. “Cope” isn’t the right word. I would say that Blood has helped me put my own sadness into words and pictures, and that was more valuable to me than any album that might make me feel better for a little bit.

Next week I’ll cover Dylan’s Top 25 Songs.


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