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Taylor Swift Is the Greatest Self-Portraitist of Our Time

Photo-Illustration: Vulture. Photo: Kevin Mazur/Getty Images

Taylor Swift is out with a new album this week called Midnights. It’s her tenth project, and it will most likely be a hit like all the other ones. But despite how autobiographical her music (and documentary) is, or at least purports to be, it still feels as if we can’t say with any certainty that we actually know her.

So Into It host Sam Sanders pondered the true meaning of Swift with Ann Powers, a critic and correspondent for NPR Music who has been thinking about Taylor Swift for as long as there has been Taylor Swift music on the radio. Read their conversation below and listen to the whole episode of Into It wherever you get your podcasts.

Into It

As the new Taylor Swift album comes to us, I think a lot about pop stars and what they mean — what their philosophy of self is. And I wanna talk about the meaning of Taylor Swift as a pop star some 15-plus years into her career. She’s harder to nail down than it might seem.
Well, one thing that always is important to remember about Taylor is where she started within country music and that sort of consummate craftsperson that she was even when she was a teenager.

There’s this idea that she’s performing damsel in distress and white vestal virgin. Well, not at all anymore, right? This idea that she writes songs just for teenage girls — not anymore. This idea that she represents women’s empowerment yet she’s been in some petty feuds with other women. I just feel conflicted and confused by her public persona more than I do with other pop stars.
If disclosure is one of her métiers, one of her main ways of operating in the world, just remember that she comes from a place where disclosure is always crafted so minutely that you can read it as a universal no matter how personal it gets. That’s what country music is. Country music is people writing songs that are deeply personal in rooms with other people, like in an office. You go into an office, and you’re gonna write a song about your brother’s alcoholism or your husband’s bad experience in Iraq or something, but you’re doing it in an office as a professional effort.

And you’re gonna workshop it.
You’re gonna workshop it, and you’re gonna look for the perfect rhyme. So I think these are sort of, like, two rival impulses within Taylor Swift. There’s the part of her that’s always gonna be that high achiever who wants to craft the perfect song and looking toward a lineage that perhaps she’s abandoned officially — but it is in her blood — of country music.

And then there is the other part of Taylor who looks to genius elders like Joni Mitchell and says, “I want to learn how to truly disclose.” I hear a constant pulling back in Taylor, a constant Oh, how much can I say? How can I say this musically in a way that still makes it relevant to a 14-year-old and her mom and her aunt and the radio program where I still want to play my music but where it feels personal? So she’s got that superego. She has the strongest superego of any artist — you know, any musical artist — we’ve ever had.

Her music is so much about order and storytelling and creating the perfect frameworks and finding the perfect characters. She’s got that intellectual side just constantly challenging her emotional side. She doesn’t seem that elusive; she just seems well managed internally. That’s frustrating for us, though.

On the one hand, she is incredibly confessional, but she’s also a very calculating pop star. Usually, those two things don’t go together, so it’s hard for me to wrap my head around that.
To make a probably completely inappropriate comparison — people are gonna jump on me big time for this — it’s kinda like Bob Dylan.

Oh my goodness. Expound. Tell me everything.
Bob Dylan’s always talked about himself as a channel for the culture and stuff, but there’s a side of him in his songwriting that’s very much about being a ruffian, an outsider. No one from the beginning to this point in his career, no one in music has been as aware of his own legacy, of his own reputation, of his own place in history, and I see that ambition in Taylor Swift. Maybe that’s what’s confusing. Because, in a patriarchal society that favors white men, how can a young woman who looks like a supermodel dare to think she could be historical? And yet she does.

She’s very much aware of where and how she wants to fit into history.
Yes, exactly.

You know, it seems her entire career, she’s been quietly chasing Joni Mitchell.

Because she knows this is a clear lineage that she wants to establish. I feel like she worries about legacy a lot more than someone like Beyoncé or Adele does, which is interesting to me.
Well, I think Beyoncé thinks about legacy in terms of her family, literally and business-wise. She’s built an empire. We call it an empire, but we can also call it a family: What am I passing on to the next generation? Culturally and politically as well, Taylor’s goals are much more individualistic, you know? I want to be remembered as a great capital-A artist. We could have a whole other conversation about if it’s even possible to inhabit the role of the great artist in our moment of virality, when everything is so fragmented. I’m not sure, but she’s gone pretty far in making the case for herself.

I find a lot of the conventional wisdom of Taylor not true or at least confusing. What is a piece of well-accepted conventional wisdom about Taylor Swift that you think isn’t really true at all?
That she’s petty. I don’t think she’s petty. I think she is embedding kinda serious messages in these very individualistic, seemingly confessional tales. I have been biting my tongue here, wanting to talk about the scarf — the immortal, famous Jake Gyllenhaal scarf — and the theory that “All Too Well” is about her losing her virginity.

Oh, interesting.
I’m not entering into the cheap discussion of whether that’s really when she lost her virginity, but it’s very interesting if you think about that song and that symbol in that way. Because then it doesn’t become petty anymore — that’s a major moment in any young person’s life. Oftentimes, what’s happening in the songs that are the most connected to a celebrity narrative is that she’s actually reaching through her personal narrative to these milestones in people’s lives and especially in the lives of the young women who are so, um, devoted to her.

If you are looking at the entire arc of Taylor Swift’s career, from “Tim McGraw” to now, and you had to make a thesis statement about that career, what is it?
Okay. She took the confessional-songwriter tradition into a new era by paying attention to everything around her and engaging with things we wouldn’t expect someone in her identity category — a young white woman to engage with the way rappers talk about themselves as well as those more conventional sources, like Joni Mitchell and the internet, all of these things. She looked at how young people are forming their identities, their own truths, and she figured out a way to write songs that spoke to that and also honored the classic lineage of confessional singer-songwriting.

In doing that, I’m never gonna call her avant-garde, but she’s far more innovative than most people give her credit for. And I think she will go down as one of the greats, inarguably, but that’s the reason. She is sharing a self that’s very much of the 21st century, very much relevant to the fragmentation of the self, to the way our selves are in dialogue with our personae. We’re all in dialogue with our Instagram feeds, and she, without making a big pronouncement about doing that, found a way to write the perfect pop song about being a human who’s also a persona. We’re all doing that now.

When I was a youth, the people who were the singer-songwriters with just a guitar, their whole shtick was “I retreat from the world for years.” And what Taylor does is say, I’m gonna be as confessional as a singer-songwriter, but I’m gonna have my eyes peeled the whole time. She has become this surprisingly successful composite of megawatt pop star and bedroom singer-songwriter. To do both as well as she’s done it for well over a decade is a feat of business and marketing and strategy whether you like the songs or not.
I totally agree. I mean, I’ve always thought that a better comparison in some ways than Joni Mitchell is Carole King. She also came out of a kind of song factory in the Brill Building, writing incredible songs like “Will You Love Me Tomorrow,” co-wrote them with her then-partner, Gerry Goffin, and then went on to make the album that many people think is the ultimate singer-songwriter album, which is Tapestry. It does exactly the same thing that you’re describing, Sam: It melds the essence of Top 40 pop with these very profound disclosures about one woman’s life. It very much connected with the exact place where women’s liberation was at the time.

It’s funny — I talked with Jia Tolentino when her book, Trick Mirror, came out, and she had this chapter about the cyborgification of popular culture. I asked her, “Who is our biggest cyborg in popular culture, like human but better?” She was like, “Oh, it’s Beyoncé. It’s Beyoncé.”
In my book, Good Booty, I wrote about Britney Spears as a cyborg. Britney’s not in control of her narrative in the same way (and wasn’t, as we all know), but she was so perfectly suited to be manipulated by technology. Her voice was the voice for that. Here’s something Taylor might not admit to or might not like but I’m gonna say: There was a reason why she wanted to work with Max Martin back in the day. I bet she was aiming for something Britney-ish. That’s something that maybe Taylor ultimately couldn’t do. I don’t think it’s about her talent, but maybe she couldn’t drain herself from the work in the way that, for whatever reason positive or negative, Britney could. She couldn’t become just a vessel for technology; she always had to reassert her personality.

And yet it has enduring appeal across generations. Taylor’s different in that you could argue that Red to 1989 is her Tapestry era, but she doesn’t really have one mega-album like that. But I do think she has a gift for making pop music her own. That’s where we’re going with this: We’re saying she is a real living woman who is also the perfect product, the perfect model. Does that make her an AI? Oh my gosh, she’s a cyborg — that’s where we’re ending up.

When I think about the version of white woman that Britney Spears was performing at her peak, it was almost white woman as sacrifice. She gave her body and her voice to the culture, to the Zeitgeist, and she said, Give me a hit, I’ll sing it. Give me a video, I’ll dance in it. I’m a vessel for you to have fun. And when Taylor would ever get that close to it, she would never give herself away enough to just become a vessel.
Oh my God, that’s so profound and true. I remember one time, years ago, I was helping curate a museum exhibit, and I went to the house where Britney’s costume designers had a bunch of her costumes, including the “Toxic” costume. They talked about how she had the perfect body to design these clothes for. Now we know how hard she had to work to maintain that body, and it really is a tragic story that kind of jumps back to the Whitney Houston story: this person who had a perfect voice and yet had to give her soul for that voice. I can’t think of one moment in her career where Taylor would be associated with sacrifice.

There’s this thing that Taylor says in her Miss Americana documentary that really stuck with me: that celebrities get frozen at the age they become famous. And when I first heard it, I said, Yeah, we’ll always see Taylor as a 15-year-old crimped-haired girl singing “Tim McGraw.” But Taylor, more than any other artist, has almost crystallized at that age in our imagination — even as she matures very clearly visually and artistically.
Oh, hell, yeah.

I don’t see Beyoncé as 17 and in Destiny’s Child anymore. I don’t see Adele as being 18, doing those first small songs and albums. Different people, right? But we still do this thing where Taylor is 15. It’s a Taylor thing, and I can’t put my finger on it, so I want you to.
I do have an answer for this, and it goes into a sensitive place. I think about the great song by the Pretenders, written by Chrissie Hynde, “Middle of the Road,” where there’s a line in that song where she says, “I’m not the cat I used to be / I’ve got a kid. I’m 33.”

Taylor doesn’t have a child. And in our patriarchal society, when does a woman change? When she becomes a mother. All the women you mentioned became mothers, and maybe one of the main reasons why we don’t accept Taylor as an adult is because the childless woman remains a strange figure in our society. We don’t know how to accept childless women as adults. I’m gonna thank you, Taylor, for not having kids yet because we really need more childless women out there showing their path.

I just always go back to high school with Taylor. Even as she’s become an adult, she still writes about high-school love and all of that — it’s very fertile ground for her. And when I think of what Taylor wants to accomplish as an artist, she wants to be a pop star who is the homecoming queen and also valedictorian. But I wonder if, with Midnights, she is turning into the former prom queen, the former valedictorian, coming back for the ten- or 15-year reunion with her shoulders down a bit and ready to tell you some stories. That’s the version of Taylor I most want to hang out with, the grown woman smoking cigarettes in the back and talking shit.
I am a little worried that her Midnights confessions might be a little mild. Who knows? We know she’s lived a little, that she’s had some wild nights. Give us a wild night. I’ll give you a cigarette.

I’ll light it up for you. Put me in a lyric. I’ll take it. I can’t help but think about her and everybody making music this year and compare them to what Beyoncé is doing. And I feel like Beyoncé has gotten to a level of fame and power where she just does exactly what she wants to do. And she made a brilliant dance album full of musical ideas and musical throwbacks just for fun and said, Take it or leave it. No videos. Here it is. What is the musical equivalent of that for someone like Taylor? Will she ever give herself up to the music enough to make her own Renaissance?
That is a good question. On Renaissance, of course Beyoncé is still present, but she gave the spotlight to others. She gave the center to others, to her historical reference points, to the queer community, to her collaborators. She even samples Big Freedia again. It’s not that I think Taylor is afraid of giving away the spotlight, exactly, but I don’t think she experiences the spotlight in that same way.

Again, her making of a self has been her artistic project. So how do you become selfless, which is what Beyoncé did on that record, when the self is really everything for you? And I don’t mean that in an insulting way. We could think of her as a self-portrait artist, the painter who paints himself over and over again. And who is in the frame if it’s not Taylor?

This interview has been condensed and edited.

Taylor Swift Is the Greatest Self-Portraitist of Our Time