Taylor Swift's Eras (Stephen's Version)

Sondheim through a Swiftian lens

Sondheim and Swift. It has a nice ring to it: purveyors or rare books, perhaps, or a much-loved detective duo. In truth, Taylor Swift and Stephen Sondheim do not seem at first glance to exist in the same creative universe; their respective bodies of work feel worlds apart. This remains true even when you strip away the usual nonsense about ‘high’ and ‘low’ art, or any other such snobberies.

But when an artist reaches the level of cultural dominance that Swift has in recent years, unusual ideas can begin to form. Creating a somewhat surreal playlist of Sondheim numbers, each pertaining to one of Swift’s eras, was one such idea—and I found that I couldn’t shake it off.

For the uninitiated, these ‘eras’ really just refer to each studio album that Swift has released, and the period of time surrounding it. She didn’t invent this framing—far from it—but she has leant into the terminology to such a degree, and so successfully (The Eras Tour is the highest-grossing tour of all time, the first to pass $1 billion in revenue), that it has entered the lexicon more widely. “I’m in my [insert adjective here] era” is becoming a more and more common phrase with each passing month.

So, here is a whirlwind (but not quite as high-grossing) tour through Sondheim’s work, viewed through a Swiftian lens. I’ve chosen one number for each era, the only rule being not to repeat any single musical. The full playlist is available at the bottom of this post. Now, without any further ado…

The “Debut”/“Taylor Swift” Era

Swift released her eponymous debut album in 2006, at the age of 16. When we listen back to any artist’s earliest work, particularly those who have since gone on to achieve megastardom, it can sometimes be hard to engage with that work on its own terms. We sift through such music, or art, or poetry, reaching through time, hoping for glimpses of these artists’ more full-fledged selves. We study the acorn, but already we see the mighty oak.

There is beauty in this perspective, of course—but it does have its limitations. Consider how we think about the work of artists who are cut off in, or before, their prime. We speak of Schubert’s Winterreise, written in the last year of his life, as a ‘late’ work; he died at the age of 31. Similarly, we cannot know what the music of, say, a 41-year-old Amy Winehouse would sound like in 2024, nor how each subsequent release might have altered our perception of Frank or Back to Black.

Fortunately, Stephen Sondheim lived to the age of 91—though the death of any artist whose work becomes a constant companion in our own lives will always, I suppose, feel premature. Perhaps that is the truest definition of timelessness. But Sondheim loomed so large for so long that we can struggle to picture his own “debut” era. Saturday Night, his first professional musical, took a little longer to come to fruition than Swift’s debut release did. Scheduled for the 1954-55 Broadway season, and with a book by Casablanca screenwriter Julius Epstein, Sondheim (still in his mid-twenties) seemed poised to burst onto the scene as composer-lyricist in some style. But the sudden death of their lead producer led to the production being shelved, and the show was not staged professionally until—wait for it—1997. Still, Saturday Night remains Sondheim’s first work. Where better to begin this playlist than with its overture?

The “Fearless” Era

Second album syndrome, or the sophomore slump, is not something that seems to have unduly troubled Taylor Swift. Fearless, her second release, was a commercial and critical success, propelling her toward mainstream prominence. Sondheim’s second show as composer-lyricist—the first to actually open on Broadway, and written after he had supplied lyrics for West Side Story and Gypsy—was likewise enormously successful. In fact, A Funny Thing Happened on the Way to the Forum’s 964-show run remains the longest of any Sondheim show on Broadway.

I did consider a number from Forum for this second entry in our playlist. “Bring Me My Bride” certainly evokes a certain kind of surface-level fearlessness, as Miles Gloriosus and his soldiers treat us to the following (outrageously good) call and response:

One, two! One, two!
We not only fought, but we won, too.
Left, right! Left, right!
There’s none of the enemy left, right?

But this is not so much bravery as braggadocio, which doesn’t seem to chime with any Swiftian notion of fearlessness. To that end, I’ve chosen “Everybody Says Don’t” as our second track. The musical that this number is from, Anyone Can Whistle, is itself pretty fearless—perhaps too much so for its first audiences, given that it closed after just 12 previews and nine performances. And within this show, “Everybody Says Don’t” perfectly encapsulates (to me, at least) that me/us-against-the-world fearlessness which is so often bread and butter for pop songs. 

For our playlist I’ve chosen the Barbra Streisand recording, for a couple of reasons. First, I enjoy how her orchestrator really showed up to work the day he was set this particular task: this version is a hair’s breadth away from being the greatest Bond theme you’ve never heard. Second, I can think of few things more musically fearless than the way Streisand sings “This time a ripple / Next time a wave.” Seriously, if you’ve never heard this version, you are in for a treat:

The “Speak Now” Era

In the title track of her third album, Speak Now, Taylor Swift really doesn’t want a wedding to go ahead. Have a look at the chorus of that song:

Don’t say yes, run away now
I’ll meet you when you’re out
Of the church, by the back door
Don’t wait or say a single vow
You need to hear me out
And they said, “Speak now”

And speak she does—though not half as much Amy does in Company. In “Getting Married Today,” Amy—or Jamie, in the partially gender-swapped recording I’ve chosen—confesses to the audience (but not to Paul, the groom) a rather extreme case of cold feet. It is a terrific patter song with a thrilling, kaleidoscopic conclusion. Unlike Swift, who offers us the perspective of the “other woman” in her scenario, Sondheim places us at the altar itself, inside his subject’s head. A fuller version of this expression, drawn from the Book of Common Prayer, is “speak now or forever hold your peace.” How typically Sondheimian it is for his character to both speak now (to us), and, from the perspective of the other characters on stage, to hold her peace too.

The “Red” Era

Swift specifically refers to her fourth release as a breakup album, with red representing the turbulent emotions that attend lost love. This is the album that includes the harder-edged, more explicitly poppy singles “I Knew You Were Trouble” and “We Are Never Ever Getting Back Together.”

Sunday in the Park with George becomes an irresistible choice of musical here for two reasons, then. First, color. In “Color and Light,” George obsessively works on his painting while Dot applies her makeup, preparing for a night out that he, as we will soon discover, has forgotten all about. “More red,” mutters George, immersed in his work; “More rouge,” sings Dot, her own brush in hand. Second, Sunday features the most terrific sort-of-breakup song, “We Do Not Belong Together”—and this is the number I’ve chosen for our playlist. It is more of a broke-up song, in truth. Dot is heavily pregnant with George’s child, but has been with her new partner Louis for some time now; Louis and Dot are due to be married and will soon leave Paris for America. Like much of Red, there is genuine anger in this number, as George and Dot argue bitterly about their relationship. Ultimately, it is a number about the capacity for self-fulfilment, which strikes me as a very Swiftian subject to explore.

Red also includes the song “All Too Well,” which is widely thought to be a chronicle of Swift’s relationship with Jake Gyllenhaal. No prizes for guessing which version of Sunday I’ve included in this playlist.

The “1989” Era

1989 is the year of Swift’s birth, and the title of her fifth album. Truthfully, it is deeply annoying that no Sondheim musical happened to premiere in that year (Assassins, first performed in 1990, is closest). But 1989, released in 2014, is a record heavily inspired by 1980s synth-pop; I therefore thought it might be nice to choose a number that Sondheim wrote in the eighties, but that specifically evokes the music of an earlier decade.

To this end, Merrily We Roll Along seemed like the right place to look. I’ve chosen “Gussie’s Opening Number,” which opens Act II of Merrily (first performed in 1981) and takes place in 1964, the year that Frank and Charley first find success on Broadway with their hit show Musical Husbands. The number itself is an excellent pastiche of an older, glitzier, perhaps showier kind of musical theater song. Sondheim, in this reverse-chronological show, plays with his own tradition in much the same way that Swift and her collaborators play with earlier synth-pop on 1989.

The “Reputation” Era

By the end of the 1989 era, Swift had largely disappeared from the public eye. Media scrutiny was increasing in general, and she became embroiled in some fairly unpleasant drama involving Kanye West and Kim Kardashian. It wasn’t until November 2017 that Swift returned to the public eye with Reputation. Its lead single, Swift’s first for three years, is the notably darker “Look What You Made Me Do.”

My choice for this era, ironically enough, comes from one of the most prolific periods of Sondheim’s career. In the 1970s alone, he gave us Company, Follies, A Little Night Music, The Frogs, Pacific Overtures, and Sweeney Todd. It is quite an astonishing workrate. But the number I’ve chosen, from Follies, could not be more fitting. Its context is of course rather different, but at the heart of “I’m Still Here” is a woman who has not only persevered through “good times and bum times” but has consistently and successfully reinvented herself, proving herself exceptionally adaptable to ever-changing circumstances. And whatever one may think of Swift or her music more generally, few would deny that she has proven herself astonishingly adept in this regard.

For this playlist, I’ve chosen Tracie Bennett’s version, from the 2018 National Theatre cast recording. You can read our conversation with Tracie, which touched on this production and on this number, by clicking here.

The “Lover” Era

Yes, it might seem a bit first-base to choose Sondheim’s Passion to represent this era, but so be it. Swift describes Lover in quite literally the least surprising terms imaginable: as “a love letter to love.” But this statement is not quite as banal as it might first seem. There is, and has been for a long time, a widespread perception that Swift only writes about heartbreak and breakups. Family Guy even crafts an entire episode around this idea: Swift falls in love with Chris Griffin, writes a song about it, and promptly gets booed by her fans for being too happy. Only when Chris dumps her mid-concert is she able to win back her audience with the angry breakup song that they all seem to crave.

And while this characterization has never been entirely fair, perhaps it does shine a different light on an album conceived as a genuine celebration of love. Similarly, Sondheim speaks of “a love that’s pure, that burns with D.H. Lawrence’s gemlike flame”—albeit “emanating from a source so gnarled and selfish”—as being central to Passion, and we see both aspects at play in the number I’ve chosen, “Just Another Love Story.” When we think about both Lover and Passion, we might ask ourselves the same question: with cynicism so dominant in our culture, could sincerity be the more rebellious creative act?

The “Folklore” Era

Swift released two albums in 2020. The first of these, Folklore, sees her explore more of an alternative pop-folk soundworld. As the world experienced its cruelest summer in many years, Swift swapped the autobiographical for the fantastical, presenting us with characters and stories of her own invention.

All roads would seem to lead to Into the Woods here, but I’m going to go in a different direction. When I think of folklore, (both the album and the word itself) I’m reminded too of Assassins and its Balladeer. Swift’s “The Last Great American Dynasty,” for example, tells the tale of Rebekah and Bill Harkness, heirs to the Harkness Standard Oil fortune; by re-embracing more of a country music narrative style, Swift draws parallels between Rebekah’s highly publicized life and her own. And by similarly leaning into the narrative potential of folk ballads, Assassins reaches across time too, connecting its characters, seeing them as part of one American story. 

I felt that our playlist needed a short, sharp burst of energy at this point, so I opted for “The Ballad of Czolgosz,” William McKinley’s assassin.

The “Evermore” Era

Swift released Evermore in December, 2020. It was a surprise album, released less than five months after Folklore; “we just couldn’t stop writing songs,” Swift wrote, introducing the album on Instagram. Crucially for our current purposes, she added, “In the past I’ve always treated albums as one-off eras … There was something different with Folklore.” So, it is debatable as to whether Evermore represents its own, distinct era.

Given this, I’ve chosen to lean more into the surprise of all these new songs being released so soon after her previous album. To this end, I’ve chosen “Next,” the final number of Pacific Overtures. “Next” charts Japan’s remarkable history from the collapse of the Tokugawa Shogunate to the present day, after the Emperor Meiji decrees that Japan will “turn our backs on ancient ways” and join the rest of the world’s industrial development. Japan’s rapid rise to global significance and market domination seems like a nice mirror for Swift’s increasingly prolific output as she moves ever-closer to her present cultural dominance.

The “Midnights” Era

I saved Into the Woods for this era because… Well, how could I not? Sondheim and Lapine give us three midnights to choose from, but the choice had to be “Last Midnight” as we near the end of this playlist. In fact, I think of this number as the finale to the playlist proper, with my very last choice acting as more of a palate-cleanser.

Midnights, Swift’s tenth album, is more concerned with nocturnal rumination than it is curses and witches, but it is not without a certain degree of fairytale-adjacent imagery. In its lead single, “Anti-Hero,” Swift describes herself as “a monster on the hill … pierced through the heart, but never killed.” But in “Last Midnight,” the Witch delivers a parting blow to those around her as incisive as it is devastating. If this were an ‘angry breakup song,’ these words would wound even the most hardened ex-lover:

You’re so nice.
You’re not good,
You’re not bad,
You’re just nice.
I’m not good,
I’m not nice,
I’m just right.

The “Tortured Poets Department” Era

And finally… For a little light relief, I couldn’t resist the fact that—given Swift’s most recent album is called The Tortured Poets Department—Sondheim presents us with a literally tortured playwright as a character. Not quite a poet, but near enough. Yes, in The Frogs, Dionysos and his slave Xanthius travel to Hades in order to bring George Bernard Shaw back from the dead. It is not the most conventional of plots.

For a more traditional ‘tortured poet’-esque Sondheim character, we might think of Henrik in A Little Night Music, who insists that his cello playing “isn’t gloomy. It’s profound.” But it seemed far more fun to end this slightly surreal journey through Taylor Swift’s eras on the most surreal note of all.

And here is the complete playlist! Comments are open on this post, so do feel free to supply your own alternative choices for any of these eras…