#149: Rough and Rowdy Ways

Ranking The “250 Greatest Albums of the 21st Century So Far” (2025)

In 2025, Rolling Stone released their list of “250 Greatest Albums of the 21st Century So Far.” I am working my way though the list, from #250 to #1, reviewing each. It’s a fascinating opportunity to revisit old favourites, and maybe discover new ones.

Bob Dylan, 2020

Alright. Now, I am a Bob Dylan fan, bigger than some, not as big as others, but I enjoy the majority of his studio albums across his nearly 60-year recording career. His 21^st century output is a bit of a mixed bag, but I generally enjoy it as well: “Love & Theft” is one of his best; I play his Christmas album each and every year, much to the chagrin of my family; I enjoyed 2012’s Tempest, though I am disappointed in the quality of the vinyl I picked up at the merch table during his tour stop in my town; “When the Deal Goes Down,” from 2006’s Modern Times, was played during my wedding ceremony (instrumental piano version played brilliantly by my brilliant aunt); 2009’s Together Through Life had some gems, like “I Feel a Change Comin’ On,” co-written with Grateful Dead lyricist Robert Hunter, as was most of the album. But his trio of albums covering standards from the mid-20th century American songbook released between 2015-2017 did not fill me with confidence about any new material that came afterward. I was sure he was done with new work and instead following his muse elsewhere.

But then came “Murder Most Foul,” a surprise 16+ minute epic about the death of John F. Kennedy, in 2020. Recorded just before the pandemic and released at just the right time, it hit #1 on the Billboard chart, the first song of his to reach that pinnacle. Rough and Rowdy Ways followed in June and it felt like the previous 8 years of touring and recording other peoples’ songs had prepared him for this. Lyrically, he’s near his best, witty and sharp and funny and poignant; his singing voice is ravaged and by no means turning back the clock - he was 78 when this was recorded, and he modified his style accordingly to match the music and the lyrics and his own diminished ability. His band, as always, is superb: Charlie Sexton, Tony Garnier, Matt Chamberlain, Donnie Herron, and Bob Britt. They sound fantastic, custodians of his legacy in the studio as in concert on his Never Ending Tour.

“Murder Most Foul” features Benmont Tench on organ, and Fiona Apple and Alan Pasqua on piano; Pasqua played on Dylan’s 1978 album Street Legal, released on June 15, 1978; born in September 1977, Apple was 9 months old.

On vinyl, this album is a double LP, with “Murder Most Foul,” the closing track, by itself on side 4. The previous 9 songs are split evenly with three apiece, creating mini-suites, no song shorter than 4 minutes. The first section, with “I Contain Multitudes,” “False Prophet,” and “My Own Version of You,” feels like 60s Dylan, with playful, cryptic lyrics. On “False Prophet” he claims “I ain’t no false prophet - I just said what I said” and then, later,

I ain’t no false prophet - I’m nobody’s bride
Can’t remember when I was born and I forgot when I died

One thing you notice right away about this album is the sheer number of words. Dylan is constantly singing - there are very few musical breaks and no choruses, creating monologues that reminded me of Blonde on Blonde or Time Out of Mind, his tales almost too full for the music. As always, the rhymes come in surprising ways, often arriving at the last moment, nearly too late. On “I Contain Multitudes,” the title refrain comes in every time, but just barely: “I rollick and I frolic with all the young dudes . . . I contain multitudes.”

The second section is “I’ve Made Up My Mind to Give Myself to You,” “Black Rider,” and “Goodbye Jimmy Reed.” The first track is a moving torch ballad, professing love and devotion in a way only Dylan can. “Black Rider” is a minimal Cash-like tune, American Recordings-style, and “Goodbye Jimmy Reed” is a rocking blues track, reminiscent of “Leopard Skin Pill-box Hat.”

The third section is the most varied and the most poignant. “Mother of Muses” is another minimal ballad, hymn-like; “Crossing the Rubicon” is another blues rocker; and “Key West (Philosopher Pirate)” is the gem of the album, an emotional ode to a place and, seemingly, to himself, contemplating fading into the sunset, Key West becoming symbolic of something else, something beyond what we currently know: “Key West is the place to be / If you’re looking for immortality.”

It’s a meditative ballad, nearly a dirge the way Dylan sings it, heavy with, I’m not sure, some feeling, maybe regret? Maybe resignation, as though he is realizing his age, the time he has left and the time he’s spent so far:

Key West is under the sun
Under the radar - under the gun
You stay to the left and then you lean to the right
Feel the sunlight on your skin
And the healing virtues of the wind
Key West - Key West is the land of light

We don’t get Dylan like this very often. He always speaks truth but usually it’s veiled, with a degree of deniability, in case he changes his mind about what he means. In “Key West,” he sings more directly: there’s no wink of the eye, no mischievous smile, no misdirection. This song tells me more about Bob Dylan as he is than any other song I can think of, moreso even than “To Ramona” or “Buckets of Rain” or “What Good Am I?” And for 9 minutes and 34 seconds, we seem to peer into his peerless soul.

Rough and Rowdy Ways surprised me. I didn’t think I would learn more about Dylan than I already knew; I didn’t think he had more to say than I had already heard. It’s a masterful record, from an artist still reaching that pinnacle that others strive for, even after 58 years and 38 studio albums. His 39^th is one of his best.