On the occasion of Bob Dylan’s 80th birthday I’ve been spurred to look at my relationship with his music, one that began with exposure to songs of his that were mainstays on mainstream “classic rock” radio and then radiated in any number of directions since then. I am inspired by his tenacity of artistic vision (even when it changes, sometimes inconveniently). And I’m awed by his truly incredible catalogue of great songs, from earth-shaking protest music to evocative poetry to continuation of folk blues and gospel traditions to flat out catchy pop songs (when I found out that he wrote Manfred Mann’s “The Mighty Quinn” for example, I was blown away that this was the same guy who was responsible for the word salad in some of his other classic songs). And while some would say his voice is an acquired taste, I guess I’ve acquired it because I love that too.

So here are ten songs, in chronological order, that demonstrate some of what I love about him, followed by a bonus sub-list of my favorite cover versions of his songs.

1 ) “A Hard Rain’s a-Gonna Fall” from The Freewheelin’ Bob Dylan (released 1963)

If I weren’t doing this chronologically, I’d likely flip these first two in order to begin with a scathingly critical protest song. As it is, though, this song (which would be my #1 in a ranked list as well) somehow encompasses that, introspection, and abstract yet incredibly evocative poetry all into one early-career masterpiece. Its structure is borrowed from the old folksong “Lord Randall,” but what Dylan does with it is simply masterful and at least to me deeply moving.

2 ) “With God On Our Side” from The Times They Are a-Changin’ (released 1964)

Speaking of scathing protest songs, this one is fascinating and chilling even if not as overtly angry as “Masters of War” or snarling like “Only A Pawn in Their Game” (both of which could easily be on this list). Instead it’s presented in a gentle, reflective manner, but the aggregate of seven-plus minutes of verse after verse challenging us to scrutinize the glorification of war is as devastating as it is profound.

3 ) “Positively 4th Street” (single) (released 1965)

This non-album single carries on the sonic fingerprint of the landmark “Like A Rolling Stone,” with a super-catchy melody and a very direct lyric (or at least direct until you start to scrutinize whether he’s lashing out at a former lover or fickle fans). Al Kooper and Mike Bloomfield shine throughout this succinct performance.

4 ) “Stuck Inside of Mobile with the Memphis Blues Again” from Blonde on Blonde (released 1966)

When I was in my mid-teens I remember calling the local rock radio station to request this one. They played it (this was back in the day when that was more of a thing) but then openly mocked his warbling vocals and the to-them impenetrable lyrics. It was the first time I realized that some people who weren’t inherently anti-Dylan carried such feelings, but it didn’t make me love the song or his performance of it any less.

5 ) “Tangled Up In Blue” from Blood on the Tracks (released 1975)

When it comes to introspective, personal storytelling songs, this is one of my favorites by any artist in any genre. The music keeps me hooked (I’d keep listening if there were twice as many verses) and by the end, I feel like I have a vivid sense of the setting and an emotionally potent relationship with the “characters” in it (to the point of wishing there were a sequel or at least an additional verse to find out if he did indeed go back again and get to her somehow).

6 ) “Hurricane” from Desire (released 1976)

Well before I had even a cursory awareness of Dylan’s early pedigree as a protest artist, I heard this song and was so moved by the story and the fierceness of the musical performance. It’s also fascinating to me that he still had this in him after over a decade of apolitical music.

7 ) “Pressing On” from Saved (released 1980)

Maybe this is weird since I’m not a Christian, but I’m rather fond of Dylan’s religious period. This song, of all those he wrote during that period, really sounds to me like it fits well into the gospel canon. Religious themes aside, the music is soulful and passionate and his vocal performances is one of the most commanding of his career.

8 ) “Silvio from Down in the Groove (released 1988)

I almost chose “Everything Is Broken” from Oh Mercy! here but the fact is that this is a list of “favorite” and not “best” or “most important” tracks. I don’t actually know how to objectively assess this song, a collaboration with Grateful Dead lyricist Robert Hunter and featuring doo-wop inspired background vocals by three Grateful Dead members (around the time they were touring together) amidst a conspicuously ‘80s-sounding production. What I do know, though, is that a) this was the first contemporary Dylan song I ever heard (that is, I heard it on the radio when it was new and not “classic”) and b) I found it delightful then and still do.

9 ) “Highlands” from Time Out of Mind (released 1997)

I enjoy long Dylan performances and the glimpse they give me into his mind, and this one is truly epic. This album and its follow-up (Love and Theft) are powerful statements in general, and this track is a particularly authoritative statement.

10 ) “This Nearly Was Mine” from Triplicate (released 2017)

I enjoy hearing Dylan cover others’ music for a couple reasons. One is that it gives a certain type of insight into his process/how he hears things, and one is that at least for certain types of material the gnarly aspects of his voice inject a pathos that supports a song’s message. This is strikingly true on this track, which showcases him and his wonderful band performing the heartbreaking song that provides a sort of emotional (if not literal) conclusion to the musical South Pacific (a song I particularly associate with avant-garde jazz pianist Cecil Taylor, who brought out the song’s heartbreak more than a half century prior, albeit in a very different way).

Top 10 favorite cover recordings of songs by Bob Dylan

1 ) “All Along the Watchtower” from Electric Ladyland by Jimi Hendrix

Possibly the definitive Dylan cover of all-time, period.

2 ) “Ballad of Hollis Brown” from Brother’s Keeper by Neville Brothers

The Nevilles bring this heartbreaking tale to the swamp without losing any of the pathos.

3 ) “I Shall Be Released” from Music from Big Pink by The Band

An early document of the Band’s long and fruitful relationship with Dylan, featuring Richard Manuel’s ethereal vocal.

4 ) “Just Like A Woman” from Here Comes the Sun by Nina Simone

Nina did a number of potent Dylan covers, and this one gets extra points for the gnarly piano intro.

5 ) “Million Miles” from Slipstream by Bonnie Raitt

Save for “Make You Feel My Love,” there are fewer covers of contemporary Dylan songs, but this is one of two excellent ones on Bonnie’s 2012 album.

6 ) “Mr. Tambourine Man” from We Used to Dance by Abbey Lincoln

Jazz versions of harmonically simply pop/rock/folk songs often leave something to be desired, but not so here thanks to Abbey’s incredibly potent vocal and a characteristically powerful band.

7 ) “Gotta Serve Somebody” from Gotta Serve Somebodythe Gospel Songs of Bob Dylan (various artists, this song performed by Shirley Caesar)

This is my favorite actual-gospel cover of a Christian-era Dylan song, drawn from a not-insignificant array of these.

8 ) “Masters of War” from Further East/Further West by Bill Frisell

The only instrumental on this list, this is actually my second favorite Bill Frisell version of this song, but included here in deference to those who like to stream – everyone else, stop now and download the version that he and Jim Hall did together.

9 ) “Highway 61 Revisited” from Second Winter by Johnny Winter

This one snarls and chugs, with authoritative slide guitar from Johnny throughout.

10 ) “Knockin’ On Heaven’s Door” from The Wind by Warren Zevon

Just because I can’t stand the Guns ‘N’ Roses version of this song (there, I said it) and am not crazy about Clapton’s (if you don’t already know it, don’t bother) doesn’t mean this song is un-coverable. This laconic yet powerful performance is the emotional epicenter of Warren’s “I’m dying but I’m going to make a record about it first” album.

Honorable mentions:

Gary Burton “I Want You”

Joan Baez “It Ain’t Me Babe”

Jeff Healy “When the Night Comes Falling from the Sky”

Manfred Mann “Mighty Quinn

Odetta “Times They Are A-Changin’”

Bryan Ferry “Make You Feel My Love”

R.L. Burnside “Everything Is Broken”

Taj Mahal “It Takes A Lot to Laugh, It Takes A Train to Cry”

Chris Smither “Visions of Johanna”

Grateful Dead “When I Paint My Masterpiece”

Byrds “It’s All Over Now Baby Blue”

Johnny Cash “Don’t Think Twice, It’s Alright”

Isley Brothers “Lay Lady Lay”



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