Why Can't Taylor Swift Do Sadness? (2024)

Happy New Year!

I have a few things in the works, including some belated posts on my 2023 reading, which have delayed themselves by getting too long and serious. In the meantime, there are other important matters that need to be addressed right away in the new year, like: why is Taylor Swift’s sad music not really that sad?

I recently discovered I had many repressed Thoughts on Taylor Swift, and also that the vulnerability of turning sadness into art might be central to my own aesthetic principles. And since this was originally intended as a music newsletter, we shall discuss.

The other night, my roommate and I were eating dinner and Billie Eilish’s “What Was I Made For?” came on Spotify. We both murmured about how good it is, and then he said, out of the blue, “You know, I don’t think Taylor has even a single song that comes close to this.” Without explanation I knew exactly what he was talking about, which we proceeded to try to pin down. “What Was I Made For?” is a near-perfect song about feeling lost and not knowing who you are, and the reason I finally cried in the generally overrated Barbie movie. The poignant lyrics, the whispered vocal, and the heavenly-choir BGVs make it a showcase of Billie’s ability to convey haunted vulnerability, and of the expressive range of her voice.

Taylor Swift has many sad songs, songs that I like and have at various moments served as the soundtrack for my own sadness. They are doubtless drawn from her real experiences and had genuine pain as an ingredient in their composition. But there’s has always been a different quality to the sadness in her music, like it’s always at some level a bit, a performance—a highly self-conscious, Important Narrative Arc in the Epic Drama of Taylor Swift, World-Historical Heroine. It’s stylized, romanticized, blown up to the cinematic proportions of her lifelong obsession with being the female lead in a wide-screen, fairy-tale love story. (I guess she has finally settled for one that airs live on ESPN.) It’s no accident that almost all of her sad songs are about breakups, and often feature as much disappointment, anger, and clap-back self-affirmation as they do broken-heartedness. What there is absolutely not, that there is in abundance in Billie Eilish’s music, is sadness as a quality that goes deeper than acute episodes of romantic misfortune, a quality that enriches us by opening us to more complex, ambivalent relational and intellectual insights. (Another friend summed this up well: “She does heartbreak, not existential sadness.”)

The point is not to say Billie is “better” than Taylor; the difference I’m describing might partly come down to Taylor being in the main an upbeat, sunny person who expects to win in life and Billie being a morose, depressive one who wonders if life is worth living at all. But when you start listening closely and diversifying the the comparisons, maybe some of it does come down to raw vocal talent. Yes, yes, Taylor can sing on the treadmill for three hours, and the physical and mental discipline required to perform something like the Eras Tour is extraordinary. It’s not that she can’t sing. It’s that the natural qualities of her voice are more limited. She can sing loudly or quietly, happily or sadly, and “emotionally” she sounds about the same.

Billie Eilish, on the other hand, has a natural vocal timbre that she wields to sound alternately wicked or despairing without ever leaving a whispery register. Her fine-grained control of her voice—the way she can hold a hush over her powerful vibrato and slide over complex phrases, like in this spine-tingling SNL performance of “Have Yourself a Merry Little Christmas”—gives her an expressive range that Taylor, and most other pop vocalists for that matter, simply lack. Only a handful of the most elite pop singers have it: Lady Gaga, for example, can sound, by turns, clubby, bluesy, rocky, or operatic, and even in her hulking, upbeat pop hits can convey a vulnerable, suffering quality that is generally absent from Taylor’s music. Yes it’s them as personalities and lyricists, but it’s also the voices they were born with that allow Billie and Lady Gaga to sounded shattered, wounded (i.e. truly sad) in a way that Taylor cannot seem to do.1

To recap: the reason Taylor’s musical expressions of sadness are somehow less convincing is partly due to her being a person who sees even her darker moments as temporary detours along a redemptive romantic arc. Historically, those expressions have been narrowly focused on romantic disappointment and not the meaning of life or its highly variegated spectrum of disappointments and tortures. That narrowness is reinforced musically by her limitations as a vocalist. Which doesn’t mean her lyrics and voice do not capture certain shards in the kaleidoscope of human experience, especially those having to do with romantic longing. Even without being very vulnerable, she has always been good at romantic emotions that are not truly sad, but range from placidly blissful (“Lover”) to hopeful elation (“Love Story,” “Message in a Bottle”) to infatuatedly frustrated (“Cruel Summer”) to wistfully melancholic (many, many, including my favorites “Tim McGraw,” “Wildest Dreams,” and “Red”). But something like vulnerability, both lyrically and vocally, is the X factor in a song like “What Was I Made For?” that is missing from most of the Taylor catalog.

Vulnerability is also at the core of my case that Midnights is Taylor’s best record and “Anti-Hero” her best song. Even if I’m not sure she is capable of the abjectness of “What Was I Made For?”, Midnights finally approaches something like suffering—an unsettled, open-ended confrontation with the fact that fantasies go unfulfilled, that there’s not always a happy ending, and that sometimes we’re the problem. For someone so long invested in being the Likable Good Girl, “Anti-Hero” in particular feels like a wrenching revision of her entire mythos, the moment where she admits that her carefully curated catalog of self-pity may in the end just be narcissism. It’s not depressive or even especially sad, but it is almost wickedly self-critical: chastened, somber, does not blame the exes or the haters or seek relief in new romantic distraction. For once there is not a shred of self-pity. Every line pithily and brutally sums up a painful admission (“I’ll stare directly at the sun but never in the mirror,” “Did you hear my covert narcissism I disguise as altruism like some kind of congressman?”) And musically it’s an absolute banger, its deceptively boppy, cheerful atmosphere setting the lyrics in relief. Taylor is not the type to really cry through song, but her self-narrating seems to be getting more expansive and varied, truer and more real—and thus closer to the quality we originally said she lacked.

“Anti-Hero” is a haunted song, maybe Taylor’s first. It shares a number of qualities with the best novel I read in 2023, Megan Nolan’s Acts of Desperation, in that it is a bracing, retrospective self-diagnosis—a kind of harsh self-awareness that comes from honestly processing a long period of delusion. (If I write about anything I read last year, it will be Acts of Desperation.) Maybe these two bits of popular culture exemplify what I’ve started to identify as some of my own aesthetic principles, mostly across the novels I read this year. I dislike extraneous detail, unnecessary adornment, pointless world-building, and virtuosic formalism; I want every bit to count, and for it to hit me where it hurts, which often requires the artist hitting themselves where it hurts. The overarching thought I had about Acts of Desperation was: there’s no question how much she suffered to be able to write like this, she clearly f*cking earned it. Maybe that’s something basic and boring like “authenticity” or “emotional truth,” or whatever is the opposite of too-knowing, too-obsequious attempts to perform something, to impress, to be liked and praised. Maybe it’s a subconsciously Christian view of suffering as redemptive and purifying. But at least I figured out there is a pattern to the art I think is good versus art I think is bad, and that every criticism of Taylor Swift is always already praise.