Bob Dylan's 'Shadows in the Night' Turns 10

“Why Try to Change Me Now?”: Bob Dylan’s Shadows in the Night at 10

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“We’ve said it before and we’ll say it again… Nobody sings Dylan like Dylan!”

So ran an advertisement for Bob Dylan’s landmark 1966 double album, Blonde on Blonde, in Billboard. Nearly 60 years and countless Dylan releases later, the tagline remains hotly debated. Just last September, I came across a thread on X where netizens revealed their “most radical position that cannot be placed on the left-right political spectrum” that posited: “Bob Dylan was one of the five greatest vocalists of the 20th century.” For every repost, there was a response of utter confusion, if not blatant disagreement: Bob Dylan’s notoriously nasally, nicotine-stained croak, a top contender for the last century’s greatest voice? Maybe it is a radical position to get behind—yet, most of the time, when I itch to hear a Dylan composition, I want to hear him sing it. I’m not a particularly spiritual person, but I believe in music, and I definitely believe in Bob Dylan—the songwriter and the singer. For me, reposting that X thread was a no-fucks-given assertion of a firmly-held faith.

There is little contention, among both casual listeners and diehard fans, regarding Dylan’s lyrical genius—it’s hard to argue against a Nobel Prize in Literature winner, after all. Conversation surrounding the pipes behind the poetry is obviously another story, though. I’ve lost count of how many times I’ve tried earnestly and patiently to convert a friend, coworker or stranger to the fruits of Dylanology, only to hear that “his songs are good, but I’d rather hear somebody else sing them.” Maybe we all can agree that nobody sings Dylan like Dylan. The truly radical claim? With a few exceptions (looking at you, Jimi Hendrix), nobody sings Dylan better than Dylan.

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I won’t argue that Dylan has some of the most awe-inspiring range (although, to be fair, it is broader than he generally gets credit for—just hear his plush croon, almost sounding like that of an alter-ego, on his joyous foray into country music, Nashville Skyline), and I’d never pull “honey” or “liquid gold” out of my bag of metaphors when describing the sounds that have come out of his mouth. I will contend, however, that pleasantness is besides the point of a “great” voice, let alone great music. No, Dylan’s voice is not particularly dulcet. But you can hear his intention surging behind every word, in every giggle and hum, in every vowel prolonged to the point of spiraling and splintering.

I listen to Dylan’s battered, delirious howls on “Idiot Wind,” and I can hear his heart popping at the seams. I listen to him stretch “Sara” into a gut-twisting, four-syllable word, and I can hear the desperation ripping through his core—he prolongs his then-wife’s name as if doing so would freeze time’s glacial passage, as if it would prevent the separation he knew was creeping closer by the second. I listen to his creaky yet confident profession of undying love on “I’ve Made Up My Mind to Give Myself to You,” and I cannot help but sigh and swoon along with each undulation of its waltz.

The latter track appears on Dylan’s 39th and most recent studio album, Rough and Rowdy Ways. Upon its release in the summer of 2020, the album achieved the deserved status of an instant classic. There is a subtle yet striking vulnerability built into these songs’ understated architectures; where instrumentation recedes, we are beckoned into open rooms in which intimate self-portraits hang and final judgements linger in the air, heavy and often haunting. The songs themselves, perhaps, are haunted—take, for example, the creepy, control-starved narrative of “My Own Version of You,” or “Murder Most Foul,” a sprawling, epic conclusion in which Dylan oscillates between a dizzying mirage of voices, memories and pop culture markers of times lost and tainted yet remembered and preserved. It’s reminiscent of T.S. Eliot’s poetry—densely allusive, each of its acts insist on close attention and analysis.

“Murder Most Foul” is the very rare song that you, the listener, feel as though you can fit into. You’re demanded to, actually: during the song’s final movement, Dylan calls upon you to keep finding the music as time cycles on. Play “Memphis in June” and “Merchant to Venice.” Play “Lonely at the Top” and “Lonely Are the Brave.” Play “Deep In a Dream” and “Driving Wheel.” Play Beethoven and Bud Powell. And, Dylan whispers as the curtains fall, “Play, ‘Murder Most Foul.’” If this were to be the last line Dylan ever sang to record (I hope it isn’t), it would be quite chillingly perfect: Here is a man aware that his own cult status rivals, if not exceeds, those of his deified predecessors. You could very well study the text of “Murder Most Foul” as you would one of Eliot’s poems—but then, you would miss the years of unspoken wisdom, love and loss enlivening his words. You would miss the sound of Dylan—then 79, thousands of songs and lives behind him—continuing to expand upon his already-inexhaustible self-mythology.

Part of why Rough and Rowdy Ways marks such a significant chapter in Dylan’s canon is that it was his first studio album of new, self-written material since 2012’s Tempest. The eight years between those releases encompassed a trilogy: Shadows in the Night, Fallen Angels and Triplicate. And, not unlike preceding Dylan triptychs, this one was somewhat of a head-scratcher. The albums consist entirely of standards from the Great American Songbook, specifically those popularized by Frank Sinatra and like-minded crooners. If any other artist burrowed within the timeworn, grossly over-annotated pages of the songbook, it would seem like they were throwing in the towel, or taking a meek final bow. As we know in 2025, this wasn’t the case for Dylan. Yet, even without the hindsight of Rough and Rowdy Ways, there was something bold about Dylan—our time’s greatest poet, as well as its most divisive voice—tackling the sometimes-sappy songs that Sinatra’s velvety baritone once made so delectable and timeless.

We’re now a decade removed from Dylan’s first gone-Sinatra record, Shadows in the Night. In the 10 years since its release, it hasn’t gone down as one of his most essential recordings, but that’s not to say it exists without merit: It’s a thoroughly handsome affair that never veers into cloying territory, certainly not a blemish on Dylan’s discography. Furthermore, it (along with Dylan’s other cover albums) offers a compelling case study of Dylan as a vocalist—as it surely did a decade ago, it might today serve as a reminder that his voice has been as integral to his enduring star power as his lyricism. Dylan sounds like he could be anyone, but no one sounds like him. Give him a song, and he will give you a piece of himself.

Dylan’s selections for Shadows in the Night’s tracklist reflect a considerable breadth of Sinatra’s oeuvre, many of the songs pulled from lesser-explored corners of the crooner’s discography. Dylan’s arrangements are sparser, less grandiose than Sinatra’s; the instrumentation is generally limited to low, mournful horns, faint pedal steel loops and gossamer webs of spindly strings. The succession of these somber, leaden tracks can feel soporific—as Stephen Deusner observes in his Pitchfork review, the album’s luxuriously moody atmosphere smothers any potential glimmers of the “sophisticated humor, feisty insight, or infectious rhythm” Sinatra famously imbued these songs with. Still, the toned-down approach plays to Dylan’s strengths as an interpreter: In peeling back the ornate layers enrobing the songs’ skeletons, he unravels the coverings that dress the songs’ wounds and reaches their cores.

Opening track “I’m a Fool to Want You” strongly sets the tone for most of what follows. A tenebrous, simmering unfurling of longing, its music’s rawness unearths the desperation—and even danger—laced through its lyrics: When Dylan hisses his urge “to share a kiss that the devil has known,” his voice curling like smoke in the air, you get the sense that there is something spectral, something wicked drawing that desire out of him. As on succeeding tracks, he doesn’t hit every high note—some cries sputter like dying motors, or burn out as unevenly as a cigarette—and there are no sweeping, full-orchestra upheavals to drown out the occasional sniffle, nor is there the post-production wizardry necessary for glossing over shaky breaths between words. Dylan sounds utterly alone on these recordings, which amplifies the intimacy the lyrics call for. His sole companion seems that of his own shadow, which feels fitting, as these songs themselves are, figuratively speaking, about shadows: the lost loves that trail Dylan’s footsteps as he paces through the darkness.

In his latest book, The Philosophy of Modern Song, Dylan notes that the alleged muse behind “I’m a Fool to Want You” (which Sinatra co-wrote) is Ava Gardner, but he determines that playing a who’s-who game is besides the point of listening: “It’s what a song makes you feel about your own life that’s important,” he asserts. And, while I must admit to occasionally indulging in YouTube shorts that parse out the love triangles and feuds that covertly (or, more often than not, overtly) permeate modern pop stars’ lyrics, I agree with Dylan: What’s so special about music is that we can make it our own.

Because we often do think of music as a space in which to find ourselves, an entity that affects us from the outside-in. A great lyric can draw blood; a great guitar solo can inebriate; a great character sketch can transplant someone miles away straight to your doorstep. However, for me, at least, some songs feel more like they unspool themselves from within my own body—there are a few rare songs that seem more like maps of myself than mirrors to it. I’m reminded of what Dylan once said about a 13th-century Italian poet’s verses: “Every one of them words rang true and glowed like burning coal, pouring off of every page like it was written in my soul, from me to you.” What that poet’s work was to Dylan is what Dylan’s work is to me. In his words, I see what my own soul aches to pronounce, but his delivery of those words—always, always more intentional than he receives credit for—is what brings them to life, what sets ablaze the pieces of coal that they are.

Personally, I do not connect as viscerally with the tracks on Shadows in the Night as with Dylan’s albums of originals. But classics are classics for a reason; there is some universal sentiment expressed by lines like “You know I’ll love ya, ’til the moon is upside down.” Lying beneath the triteness of such lyrics is a giddiness that is absolutely real, and which Dylan’s performances properly excavate. “Why Try To Change Me Now” is particularly affecting, a rare glimpse of Dylan at his most tender. As he confesses to sentimentality against a backdrop of starlit strings and woozy pedal steel, you can almost hear—a smile?! It surely sounds like it: Listen closely, and hear how light and, frankly, sweet he sounds as he reflects on his daydreams and the romanticism of walking in the rain. Dylan was 73 when Shadows in the Night was released, but he sounds young-and-in-love—still in awe of the moonbeams that douse the night’s shadows in light, however silly that might be.

The songs Dylan performs on Shadows in the Night are simplistic compared to his own, but perhaps that is why they have endured for so long—they are open to any voice to step inside and reshape. It is up to the artist to make these classics “ring true” to their own lives and those of listeners, and Dylan succeeds. It’s impossible to say who or what he might have been thinking about as he recorded each song; nevertheless, he seems to color each with his own personality and decades’ worth of romance, heartbreak and regret. For example, his grizzled vibrato profoundly deepens the wistfulness and poignancy of “Autumn Leaves”: It sounds like his sorrow for a lost love has only weighed more heavily upon him as seasons have come and gone. “Stay With Me”—a true standout—likewise portrays a sincere, potent ache that’s only sharpened with time. “Should my feet sometimes stumble on the way, stay with me,” he implores, his weathered cry quite literally faltering and crumbling “on the way.” From a young Sinatra, these words make for an irresistible, smooth seduction—I’d wager that he has a pretty good chance of getting his girl back. Dylan? Not so much. But I’m willing to bet more of us will hear ourselves—whether we want to or not—in his weary, run-down rasp.

Shadows in the Night is a record rife with uncertainty, three of its tracks’ titles alone (“Where Are You?” “What’ll I Do?” “Why Try to Change Me Now”) posing questions. Particularly, Dylan spends much time pondering love: “Who can explain it? Who can tell you why? Fools give you reasons, wise men never try,” he sings on “Some Enchanted Evening.” We tend to think of him as possessing some singular wisdom, some grasp on the most untouchable concepts in life, those which we feign to comprehend. To be fair, if anyone might make sense of love, it probably would be the bard behind “To Make You Feel My Love,” “Sad-Eyed Lady of the Lowlands” and other breathtaking odes. But ultimately, Dylan is just as human as any one of us. We know he’s capable of much more throat-catching, heart-shattering lines than those on Shadows in the Night, which often do deal in melodrama. Some evoke rather saccharine scenes: “Tonight I’ll use the magic moon to wish upon, and next full moon, if my one wish comes true, my empty arms will be filled with you,” Dylan warbles on “Full Moon and Empty Arms.” To wish upon the moon—does it border on cheesiness? Sure. But love makes fools of us all, even Dylan.

The unexpected vulnerability and tenderness with which Dylan inflects these songs are enough to make Shadows in the Night a worthwhile listen. The album might not have warranted two follow-ups (practically, four, considering Triplicate’s triple album status), and Rough and Rowdy Ways certainly served as a reminder of how dearly missed Dylan’s lyricism was. Even still, Shadows in the Night is an elegant, fine addition to Dylan’s canon and ample proof that the guy can sing—quite affectingly and, when he wants to, even quite beautifully. Not that Dylan cared to convince you of that—when has he tried to win anyone over? He’s gone electric. He’s gone Christian. He’s even gone Christmas. He’s done it all, and he’s admittedly done some things better than others.

But it’s his boldness, hunger to grow and undeniable love for his craft that make him the singular artist he is. I wouldn’t want to change anything he’s done; I wouldn’t try to even if I could—every song he’s sung is a piece to the puzzle of the artist and man he is. But if Shadows in the Night’s existence must be justified by one track, it would be its rapturous grande finale, “That Lucky Old Sun.” And, if Dylan’s singing “That Lucky Old Sun” must be justified for one reason, it would be its final stanza. The verses are an exhausting uphill climb, but their destination is one of Dylan’s most stunning vocal performances of his career, both wrought with emotion and technically superb. Listen to the upswell of his voice on those final words as a symphony of strings ecstatically rises to meet him, and then try telling me he can’t sing.

Read: “Bob Dylan’s 62 Greatest Songs of All Time, Ranked”

Anna Pichler is one of Paste’s music interns. When she’s not writing about music, she’s working towards an undergraduate degree in English Literature from The Ohio State University. You can find her on X @_Anna_pichler_ and Bluesky @annapichler.bsky.social, where she mainly shares her work and reposts her favorite Bob Dylan memes.

“Why Try to Change Me Now?”: Bob Dylan’s Shadows in the Night at 10

Dylan was 73 when his 36th album was released, but he sounds young and in love—still in awe of the moonbeams that douse the night’s shadows in light, however silly that might be.