Taylored Regrets

Swift reckons with the ghosts of history, personal and musical, in 'Midnights'

In the early 1950s, Frank Sinatra was left for dead as a pop star. A decade earlier, he had burst into public consciousness primarily as a singer for teenage girls—they literally rioted at his shows—and went on to become a major media figure with his own radio program, starring roles in movies, and international tours. But celebrity is inherently ephemeral, and Sinatra severely damaged his own brand with his notorious behavior, which included a tempestuous extramarital affair—and a brief, tempestuous marriage—with screen goddess Ava Gardner that led to what we would today call his cancellation. Dropped by his label, shunned by the media, and experiencing voice problems, he was thrown back on himself, faced with the indifference and hostility of a public that had moved on.

In this moment of personal crisis, Sinatra, now in his mid-thirties and forced to finance his own work, turned to emerging musical technologies. His first records had been recorded on ten-inch shellac discs, which were fragile and relatively poor in recording quality. But in the late 1940s, two new formats—the seven-inch vinyl single disc (which could hold a single song on each side) and the twelve-inch so-called “long-playing” vinyl record (or LP) could hold about 20 minutes of music on each side—entered mass circulation. Sinatra was particularly fascinated with the LP. He developed a concept of a suite of songs whose whole was greater than the sum of its parts—to borrow a photographic metaphor, an “album.” When Capitol Records took a flyer on him, the record was released in 1955 as In the Wee Small Hours, a collection of melancholy reflections for late at night. In the years that followed, Sinatra would release a series of other such albums, among them the joyous Come Fly with Me in 1957 (on the novel experience of jet travel) and the gin-soaked Frank Sinatra Sings for Only the Lonely in 1958 (a suite of melancholy saloon songs). His career was resurrected.

I don’t know if Taylor Swift is familiar with Sinatra’s In the Wee Small Hours. My guess is yes: she has demonstrated an acute sense of musical history from the very beginning that is reflected in songs that range from the early Beatlesque “Speak Now” to the slyly harmonica-rich, Dylan-bitter “I Bet You Still Think about Me” to the Cranberries-by-way-of U2 “State of Grace.” In any event, she is distinctly old-school in her commitment to the album as the core unit of her record-making, which continues to shape her career even in the age of streaming. So it seems fitting that her latest release fits squarely in the album tradition as she heads into what appears to be the middle of her career. With assiduously managed salescraft, she has already moved a million copies of her latest, Midnights, at a time when most people listen to music by subscription. (I bought a copy in the dominant format of my time, the compact disc.)

One key difference between Sinatra and Swift is that while Sinatra was primarily a peerless interpreter of other peoples’ songs, Swift stakes her identity on her songwriting. She crafts choruses of McCartneyesque catchiness, builds sturdy bridges, and writes lyrics that sing (“flying in a dream/stars by the pocketful” goes one colorful line from the evocative “Snow on the Beach”). She has also addressed the weak link of her singing, which will never achieve Sinatra’s polish but is more than serviceable.

Swift’s last two albums, Folkore and Evermore, released in uncharacteristically quick succession amid Covid in 2020, were largely acoustic records. And one might have imagined that a late-night album would have that palette as well—maybe something on the order of Joni Mitchell’s 1971 classic Blue. But the dominant tonality of Midnights comes from Swift’s synthesizer- and drum-machine-dominated Reputation (2017). Truth be told, it’s not my favorite record (though “Getaway Car” is a masterpiece that ranks with anything she’s ever done). Swift is not someone who chases trends—like Beyoncé, she tends to float above genres rather than reside in them—but it is perhaps inevitable that she would seek to maintain currency by the standards of contemporary popular music. Her current number-one song in the country, the self-loathing anthem “Anti-Hero,” sounds right at home in the Billboard Hot 100, even as one can hear the echoes of ’80s synth-pop that has been part of her musical frame of reference since her 2014 album 1989, the commercial apex of her career. She and producer Jack Antonoff seem to have picked up the thread of a highlight from that record, “Out of the Woods,” and really run with it here.

Though it took me a couple of cycles to really hear it, Midnights does indeed evoke wee small hours in its wash of reverb and minor chords. The album begins with the dark, smoky sounds of Lavender Haze, which has a dance-club feel, along with more dreamy tracks like “Maroon” and “Snow on the Beach.” The cumulative impact of the thirteen songs is musically cohesive. Roxy Music Avalon cohesive. Elton John Captain Fantastic and the Brown-Dirt Cowboy cohesive. (“Someone Saved My Life Tonight”: now that’s music for four o’clock in the morning.)

Swift’s great subject here, as usual, is herself. Regret is the dominant theme. Many of these songs, notably “Midnight Rain” and “Question…?,” seem to be about men who got away—or she got away from—only to have them return to the bedchamber of her memory. Swift also continues to flash the thin skin she’s exposed at least since “Mean,” calibrated more effectively here in “Bejeweled” and less so with “Karma.” Such songs are sometimes wrapped in the mantle of feminist self-assertion, as in the case of “Vigilante Shit.” As she herself seems to recognize in “Anti-Hero,” however, she can seem like an unseemly avenger.

Not all reflections on the pane of the past are sorrowful. “You’re on Your Own, Kid” has an expectant pulse that ends on a note of affirmation in her choice to leave small-town life—“from sprinkler splashes to fireplace ashes”—behind. And as the album comes to a close, there are signs of daylight with the fraught-but hopeful “Labyrinth,” as well as “Sweet Nothing,” in which she cherishes the intimacy of a companion far from the madding crowd. In the album’s final track, “Mastermind,” a self-described Machiavellian explains how she deploys her powers for the greater good of love:

You see, all the wisest women
Had to do it this way
'Cause we were born to be the pawn
In every lover's game…

I'm the wind in our free-flowing sails
And the liquor in our cocktails

Taylor Swift now is about about the age that Frank Sinatra was when his career hit the skids. I don’t expect her standing to founder the way his did—for one thing, she has behaved better—but she’s not going to be the belle of the billboard forever. (Indeed, this is something she has been fretting about for a while; see, for example, “The Lucky One,” already a decade old.) Like Sinatra, she will lose the pubescent female shock troops that rocket-fueled both their careers, holding on to an audience that will age along with her. Half her lifetime ago, she burst onto the scene as a charming prodigy whose sheer ingenuousness demolished clichés with her freshness and candor. Now she’s a (not) old pro. I confess I’ve found myself wishing that she would choose to revisit the country idiom in which she showed such mastery—Loretta and Dolly can show the way—or take on other themes beyond those that have preoccupied her over the course of the last two decades. One never stops revisiting ones who got away in the middle of the night. But the landscape of the wee small hours also gets populated by one’s children (real children, not the imagined covetous daughter-in-law of “Anti-Hero”) who keep you up at night, and the specters of loved ones gone but not forgotten. A wider world awaits, in darkness and light.

But Taylor Swift doesn’t need advice from an old man fan. Frankly, she’ll do it her way.