This is the first in a series of year-end posts about some favorite works of art that I first encountered in 2020. It will be followed by pieces on my favorite books and films.

2020 has sucked for all sorts of reasons. Observing strict COVID-19/social distancing guidelines means that I’ve spent less time with family and friends than ever before; what I assumed would be my busiest and most productive year as an artist has ended up being the exact opposite; and, as an adjunct college professor, I’ve had to re-learn my trade from the ground up as I’ve transitioned into teaching classes online exclusively. In order to maintain perspective, I’ve had to remind myself that I’ve been a lot luckier than some other folks I know: Unlike friends and colleagues who have been laid off, I’ve at least been able to work from home and continue earning a steady paycheck. Being at home more often also means that I’ve spent more time consuming art — mainly, literature, music and movies — than I have in a single calendar year in decades, maybe ever. The work of art that I’ve turned to for comfort more than any other during this tumultuous time has been “Key West (Philosopher Pirate),” the penultimate track from Bob Dylan’s terrific Rough and Rowdy Ways album, which was released in June. I’ve listened to this song literally hundreds of times already, often on headphones while walking around the north side of Chicago wearing a quarantine mask, and it’s never failed to be a transporting and cathartic experience.

I think it’s productive to regard “Key West” as Dylan’s own version of “Over the Rainbow,” a song originally written by Harold Arlen and Yip Harburg for The Wizard of Oz and sung by Judy Garland’s Dorothy in response to her Auntie Em’s advice to find a place where there isn’t any trouble. Dylan, who described “Over the Rainbow” as “cosmic” in his 2004 memoir Chronicles Volume 1, makes an explicit nod to The Wizard of Oz in “Key West” when he sings, “I’ve never lived in the land of Oz / Or wasted my time with an unworthy cause.” Beginning with a disturbing description of hearing the assassination of William McKinley on a pirate radio station, Dylan’s song specifically details the act of traveling to Key West, a destination the narrator posits as a mythical place free of trouble, a “paradise divine” that appears “on the horizon line.” The subject of the song is the thin line between life and death, and Dylan uses Key West, a place where he apparently spent a considerable amount of time decades ago, as a metaphor for some kind of peaceful afterlife. The lyrics and Dylan’s phrasing are perfect: There are literally dozens of magical vocal moments scattered across the song’s nine-and-a-half minutes (e.g., “…if you got something to confess,” “Bougainvillea blooming,” “…gold fringes on her wedding dress,” etc.). But what truly elevates the track to heaven’s door, to that rarefied sphere of Dylan’s greatest achievements, is the genius accordion playing of Donnie Herron, the multi-instrumentalist and stealth MVP of Dylan’s live band for the past 15 years. Herron’s accordion here becomes the aural personification of a gentle Florida breeze, warmly embodying the “healing virtues of the wind” that Dylan so memorably sings about.

“Key West” also has meaningful and substantial connections to “Murder Most Foul,” the already-notorious, 17-minute epic about American popular culture in the wake of JFK’s assassination that follows it on the album. In addition to being concerned with the murders of Presidents and the act of listening to the radio, both songs also share similar lyrics: The phrases “down in the boondocks” and “going down slow” in “Key West,” for example, cleverly become literal song titles that are quoted in “Murder Most Foul.” Conversely, some of the lines in “Murder Most Foul” (e.g., “the man who fell down dead like a rootless tree”) appear to have been composed in pointed contrast to certain lines in “Key West” (e.g., “I’ve got both my feet planted square on the ground”). But the most important connection between the songs comes in the “Key West” lyric “I heard your last request,” which seems to refer to the final, self-reflexive line of “Murder Most Foul” (after a litany of other requests: “Play ‘Murder Most Foul'”). It is as if the narrators of the songs are in dialogue with each other — the narrator of “Key West” hearing and fulfilling the dying wish of the narrator of “Murder Most Foul” (who may be JFK himself) — thus creating an eternal two-song circle within an album full of other such circles (add the Julius Caesar-themed “Crossing the Rubicon” to these two, for instance, and you have a trilogy dealing with political assassination). Making these kinds of connections has always been part of the fun of listening to Bob Dylan, of course, but the songs on Rough and Rowdy Ways offer an exceptionally intricate, Joycean web in which listeners can get lost if they so choose. And I emphatically choose to do so. Such is life, such is happiness.

For those who don’t already own Rough and Rowdy Ways (and, if you don’t, what’s wrong with you?), you can listen to “Key West (Philosopher Pirate)” on YouTube here:

You can read more of my thoughts on Rough and Rowdy Ways here. My buddy (and Flickering Empire co-author) Adam Selzer expounds on the connections between “Key West” and “Over the Rainbow” at length here.

For the record, my top five favorite albums of the year are:

5. Emma Swift – Blonde on the Tracks
4. Haim – Women in Music Pt. III
3. Run the Jewels – RTJ4
2. Fiona Apple – Fetch the Bolt Cutters
1. Bob Dylan – Rough and Rowdy Ways