Ranking ten (slightly) lesser-known examples of Bob Dylan’s lyrical genius

Bob Dylan can now add Nobel Laureate to his growing list of awards and honors. Despite some tsk-tsks from various corners of the literary world, the prize has been long overdue. Dylan’s oeuvre, its breadth and its depth, is unparalleled when you consider his vast reach as a popular poet. This is a subjective ranking of some lesser-known lyrical masterpieces. These songs aren’t obscure cuts. But they’re (relatively recent) works a casual listener wouldn’t stumble across on a best-of compilation. For that very reason, they best demonstrate why Dylan earned literature’s top accolade — even his secondary and tertiary works stride across the cultural firmament.

You can listen to this collection as a Spotify playlist too.

10. “Lily, Rosemary, and the Jack of Hearts”

A rollicking heist narrative that most people, no doubt, skip over on Blood on the Tracks to get from “Meet Me in the Morning” to “If You See Her, Say Hello”. What a mistake! Dylan paints his storytelling masterpiece on “Lily, Rosemary, and the Jack of Hearts”. It’s a saloon caper, and more importantly, a thrilling plot set to song.

9. “High Water (For Charley Patton)”

This apocalyptic track became instantly prophetic when “Love and Theft” was released on September 11, 2001. Dylan sings of the cuckoo, a winged parasite, whistling an avian tune while fluttering above human wreckage. His vision of an underwater hell went from figurative to literal, four years later, when the levees broke in Louisiana.

8. “Every Grain of Sand”

The single best result of Dylan’s brief conversion to Christianity. A hymn about the sublime — be it the result of God or nature — overtaking a great artist, and a broken man.

7. “Thunder on the Mountain”

The old coot embraces aging, and his elevated legacy, with a lascivious grin. Unlike on “High Water”, the End Times, on “Thunder on the Mountain”, are fun times. Dylan is the happy warrior heading into the final battle, just looking for a kiss.

6. “Isis”

Egyptian mythology provides the template for Dylan, here at his most swirling and surrealistic this side of “Mr. Tambourine Man”. “Isis” is a love song, and a song of love lost, turned into a vision quest. Heartbreak is sent through the kaleidoscope and emerges fractured, a little unintelligible, and powerful nonetheless.

5. “Not Dark Yet”

Death haunts Dylan on “Not Dark Yet”, but he only half-shivers at its specter. He’s too tired and bruised to worry or fret. Instead, he looks back, shrugs, and stumbles onward.

4. “Idiot Wind”

The bitterest fruit of Dylan’s catalog. A breakup song so angry, it’s hard to parse its imagery. Which is, of course, the point. This is bile, so potent, that it only sometimes rhymes.

3. “The Lonesome Death of Hattie Carroll”

Dylan, in ‘60s protest mode, goes strikingly literal (as he later would on “Hurricane”). Plain and devastating, this song seems relevant as ever, more than fifty years hence. Today’s racial injustices are summed up in its final lyric: “Oh, but you who philosophize disgrace and criticize all fears/ Bury the rag deep in your face/ For now’s the time for your tears.”

2. “Mississippi”

A magnificent and ambivalent ode…to what exactly? A failed relationship? Dreams unfulfilled? Existential regret? Depending on where you are in life, “Mississippi” can offer a necessary salve for any of these downsides. Perseverance is its theme and, yet, “the emptiness is endless.” Dylan serves up hope with a chaser of truth, which is “cold as the clay.”

1. “Blind Willie McTell”

Elegant and elegiac, “Blind Willie McTell” is the one that almost got away. Recorded during the Infidels sessions, this song, the finest of Dylan’s post-Blood on the Tracks work, was originally locked in the vault. When it finally emerged in 1991, on the first Bootleg Series release, early murmurings about its splendor were confirmed — and then some. Not only is it the prime example of a diamond unearthed from unreleased coal, “Blind Willie McTell” stands proudly next to, and maybe even above, many of Bob Dylan’s cherished compositions.

Through the lens of the relatively unknown blues singer, Dylan focuses on slavery, “all the way from New Orleans/ To Jerusalem.” But his imagery then settles on the Antebellum South and beyond. The moral sorrow and biblical outrage becomes overwhelming. Dylan, despondent, knows he can’t truly empathize as a white man, or even as a Jewish man: “No one can sing the blues/ Like Blind Willie McTell.”