Taylor Swift: A Conversation

Posted: by The Editor

Photograph by Kyle Musser

On the weekend of July 7, 2023, Taylor Swift released Speak Now (Taylor’s Version), the re-recorded version of her third album from 2010. While I enjoyed some albums and songs of Swift’s over the years, I was never fully able to understand her mass appeal; I always held on to some dislike for her seemingly repetitive themes of relationships and love as well as her diehard fan base. I spent some time that weekend listening to the re-released Speak Now in the car with my best friend, and we proceeded to have a two hour conversation about Taylor Swift and what is truly going on behind her brand. Lately, she’s become a global superstar, with her tickets reselling for thousands of dollars and the fan base becoming even more rabid, which has intrigued and confused me since the Eras Tour Ticketmaster debacle. Then I realized I worked for this music website! I could find out the answers to my questions! I decided to gather some of the Taylor Swift fans at The Alternative and talk through her discography, tour experiences, and the brand. I spent the two weeks preparing for this conversation listening to all of her albums, watching Miss Americana, browsing Swiftie TikTok, and discovering that maybe I do like Taylor Swift’s music after all. – Madison Van Houten

This conversation has been edited for length and clarity.

Madison Van Houten: Hi Swifties! Before we start, I just wanted to reiterate that my position here isn’t anti-Taylor Swift. I like some of her music. I do like some things she’s done, but with the re-release of Speak Now, I was listening to it and having a conversation with a friend about what the deal is around her – why people have become so obsessed in the past few years, and why she’s blown up past say, the level of Lady Gaga or Ariana Grande to become a global star. To start, I want to know what everybody’s entry point into Taylor Swift was. 

Ryleigh Wann: Taylor Swift was my first concert. Before that, I remember I had a neighbor who had the debut CD and we listened to it a lot. I didn’t have many CDs of my own at the time, and then I started just buying them and getting gifted the different albums.  The Speak Now tour was my first time seeing her live. It was at Ford Field in Detroit, and I went with my dad and my friend and we wore cowboy hats. And it was pretty goofy. And then after that, I was like hitting almost every show, as she came to Detroit pretty often.

Hope Ankley: I think mine was the album Fearless. I think I bought it by myself. I was in middle school and I remember I cried over this boy all the time and who made fun of my arm hair and also cheated on me. I just remember that album really spoke to me because of that and I think as an adolescent girl experiencing like all those overwhelming emotions, liking boys, growing up, weird, terrifying parts of life when you’re 14 years old. I felt like she just was so similar to her music back then, kind of. I think it touched the younger demographic that way because she was also very young. As I grew older and she re-released a lot of these albums it brought me back to that time period and made me realize why I like her older stuff a lot more than her newer stuff. Because she wrote from a very youthful spirit and she was unapologetic about not being an adult. And I thought back then there was no one really doing that at her age. And I think that’s why so many people kind of grabbed onto her at that time and stayed loyal over the years.

Zac Djamoos: I have a completely different perspective because I got into Taylor Swift through 1989. Because at the time when she was really ascending, I was also in middle school and so I was in my “I’m listening to The Wonder Years and I’m 13 and I’m too cool to listen to anything on the radio” era. And I think I started listening to Lorde. Because Lorde was my “I can listen to pop music without feeling like I’m listening to pop music.” I remember when, like she released “Blank Space” as a single, I was like, oh shit. Taylor Swift is making a Lorde song. And so I sort of ironically liked it. And then I just like liked it. I thought alright, you know, maybe I should grow up and just listen to the album. Worst thing that happens is I hate it and I get to  make fun of it, and I was like, oh shit, this is fun, and it rocks, and I got really into it. My sister and I went to see her on that tour, and it was incredible. And I bought the shirt that says I heart Taylor Swift. To this day, my students try to blackmail me with that, as though it’s not like, the proudest moment of my life. 

Madison: I guess I’m more similar to Hope and Ryleigh. I remember listening to Speak Now all the time; it was 2010. I used to go to my best friend’s house after school and we would watch Degrassi and listen to the album. I was thinking about, oh my God, I wish somebody would only love me the way she describes in “Mine.” And I liked to escape into the little teenage fantasies that came with a lot of those songs. But I also remember that at the time I felt bitter towards her because she was writing all these songs about heartbreak and being lonely, and yet she was publicly dating all these hot men, like Taylor Lautner, John Mayer. My 14 year old self hadn’t even been kissed yet, and I didn’t feel like she had the right to complain when she got to date all these hot guys. Which is so stupid and immature, but at the time, it was how I felt.

So I carried that annoyance with me for a long time. But I will say that 1989 for me, is my favorite album, and a fantastic one. I’m also a Jack Antonoff fan, so I feel like that plays into it, as a lot of it feels like a Bleachers album. 

Zac: Jack Antonoff. The only reason people hate him, I’m allowed to say this, is because they hate to see a Jewish man from New Jersey on top. That’s true. That’s the same reason people on the Internet don’t like me. It’s all antisemitism and I’m leaving the chat now. I’m done. 

Madison: But when he recorded that album with her, that was when she launched into superstardom! It’s very impersonal as compared to her older stuff, but it is I guess, more accessible, a bit more basic music.

Hope: That’s when she really shifted to pop music. That was like that was the overexposure moment. 

It’s so weird because I didn’t like 1989. And I think it’s because I didn’t like her during that period at all. She was everywhere. She had her model girl gang with her at. Her feud with Katy Perry, she was having celebrities at her apartment all the time, everyone was at her lake house, and I was just sick of seeing her. So I refused to listen to the album and I still haven’t listened to it in the whole I think now because it just brings me back to 2014. 

Zac: That’s a really interesting one. It is definitely like the beginning of Taylor Swift. The brand, I guess, which is unfortunate. I think that was the first album of hers to get like a deluxe edition, right? 

Hope: Hmm, I think so. 

Zac: Red is 20 fucking songs, isn’t it? We don’t need a deluxe version of that. If I start talking about this, Red people are gonna get mad at me. Red is not very good. 

Madison: Yes, 1989 did have a deluxe edition. A whole 22 tracks.

Ryleigh: I wasn’t too into Red either. But my attitude was a little similar to how Hope was, where  I always would joke and say Taylor Swift was my dirty secret. I remember taking photos at the concert on my digital camera and not posting them on social media so no one would see. I never really thought about 1989 as being the beginning of the brand, but it totally was because she also had the secret sets in the middle of the shows. She had Imagine Dragons come on the stage and I was like, whatever. That’s cool I guess.

Hope: I think it’s because she shifted to pop and maybe that’s why they really tried to brand her hard to get her away from country music.

Ryleigh: She had to hide that fake accent, right? I never knew she was from Pennsylvania until recently when she was saying “Philly is my hometown show!”  Aren’t you from Knoxville or something? Dude, I don’t know. It’s very funny. Or Nashville. I thought she was from Tennessee. 

Madison: Alright, so I said 1989 was my favorite album, but I want to get to the hater portion of the conversation. It’s the 1989 era, she’s really big here, on top of the world. And then we had the insane fall from grace because of the Kanye West “Fade” lyrics scandal, her snake era. I remember when the “Look What You Made Me Do video” dropped; I was on vacation with a friend. We went back to our room and we’re like, okay, buckle up, let’s see what she has to say!

I’ve been revisiting Reputation this week, and to this day I think the album is mostly hot garbage. At that time I really started actively disliking Taylor Swift, and this music is bad, and it’s freaking me out that everyone is worshipping her, because this is bad, and I need everyone to acknowledge it. 

Hope: It’s trash. I know a lot of Swifties are trying to reclaim Reputation. I’ve seen that a lot but I can’t. It’s too cringy for me. She’s trying to make a point but doing it very badly. 

Zac: It also has Photoshop album art. 

Hope: The newspaper was so bad. 

Zac: Reputation is not good. Let’s put it like this: 1989 is like when Wendy’s gets on Twitter and is posting about like “ha ha ha i’m so depressed” then Reputation is the one where Steak-Umms gets on Twitter and is like “You should kill yourself. You should fucking die.” It’s her heel turn album, but in the worst possible way which really sucks. People get mad at me for saying this, but “Look What You Made Me Do” is a really good song. That song whips. It’s so much fun. It’s so much fun and the rest of it, like, lacks the fun, and it also has a Future and Ed Sheeran collab song. 

Hope: I will say that Reputation hits so good live. When I saw it for Eras Tour it hit so hard. 

Ryleigh: I went to the Reputation tour because my friend won tickets, and I ended up in the front row, which is insane thinking about the prices people are paying now. And it was super fucking sick. And I didn’t love the album. I thought,  I’m going to get lit and hang out, and it was so cool. I remember “Call It What You Want” was fire. If you lean into the cringe, it’s not bad, the microphone was a snake and she’s in this little cage and floating all around the stage. I don’t know. It’s definitely pretty goofy, but I was just like OK, girl, be mad. I’m so surprised you said “Look What You Made Me Do” is a great song. I can’t get past it.

Zac: So for me, I understand what she’s trying to do; it’s like the scene in Game of Thrones, where Tyrion’s on trial and he says, well, now I’m going to be the monster you think I am. They’re trying to do that and I get it, but it’s very dour and it’s very bland. It’s like what Ava Max is doing now. It’s the most faceless music and just very, very uninspired, like songwriting. And the reason why I like “Look What You Made Me Do” is because it’s so over the top that it’s the only song where I feel like she believes it, but I do agree with you. However, “Call It What You Want”, gun to my head right now, might be my favorite Taylor Swift song. That’s a perfect song. 

Madison: For the most part, it doesn’t feel like her. It doesn’t feel like the brand that she’s created. And like, it’s hard to believe her as, like, a bad-ass wearing a gold chain and dark lipstick.

Ryleigh: Another album that I don’t care for is Lover

(Hope, Zac, and Madison all look visibly shocked.)

Hope: That’s what brought me back into it. 

Madison: I totally disagree with that. 

Ryleigh: When it first came out in 2019, I just don’t know, I was so disappointed by it. I was. Maybe it was too poppy for me. Besides “Cruel Summer”, though, which was obviously great, why wasn’t that the single off of the album? But then when I saw her perform, she did a couple of the songs live, like “Archer”, which made me go OHHHH I GET IT NOW. Maybe I’m just one of those people. I’ve got to see something live before I really like it.

Madison: I liked it a lot. I was already planning to hate it before it even came out. But Lover was like a return to form. The songwriting was way better. She was so insincere on Reputation and then it went back to, oh, you know what? Actually I can wear pink and I can write twenty songs about the same man and we will eat all of it up. 

Hope: I think because I hadn’t listened to a Taylor Swift album in full since 2013, when this publication forced me to write the Lover album for review, that’s what caused me to come back to it. 

I realized I actually like this, I was thinking it was going to be like Reputation. And then I heard “Cornelia Street”. And that’s like my favorite song of hers, ever. And I don’t know why, but it makes me cry every time I listen to it. When that made me cry the first time I listened to it, I said, damn, I guess I’m back. Back on the Taylor Swift train. 

Zac: I think Lover is probably my favorite and there’s some really bad stuff on there. Like “I Forgot That You Existed” is…not good. As well as obviously “Me!” and “You Need to Calm Down”. 

Madison: That’s fair and correct. 

Zac: “Me!” made me wish I was dead. A lot of it feels like a more adult version of Red to me. When people talk about Red, they say it’s a generational album from a pop star. I don’t really see it with that one, but Lover to me is definitely that, I think. 

Hope: Oh no, but my favorite album would probably be Red! Or folklore because folklore is like she was taken out of it; she took herself completely out of the albums. You  really see her storytelling and lyricism shine during that period, and it’s not about her. It’s about like a world she built within it. 

Ryleigh: Yep, huge folklore and evermore fan.. I’m a little bummed out that those two albums didn’t get their own tour like their own. 

Madison: That is where the wheels start to fall off for me again. I know people really love evermore and folklore, and I think it’s a personal preference, as I like music that moves faster and quicker. But I felt like the last three albums, I’ll include Midnights in this, were all a bit slower. It felt like a retread of thoughts and topics that I had heard before. I feel like in her songwriting, she got famous when she was like 14/15, and they talk about how lightning strikes when you get famous. People love the Karma song, and to me, I think, this sounds like we’re still singing like a 15 year old. Even the similarities in song content in mirrorball and Bejeweled, to me, I feel like we have one song on every album about how she is shimmering.

Hope: I didn’t like Midnights!

Madison: I feel like the world exploded when she released Midnights and then it got even crazier with The Eras tour, and it’s just come to this insane head that has never existed before. 

Ryleigh: I wish she would have lingered in the weird indie phase, though. Experiment. I was like, yeah, dude, get acoustic with it. Bring the dude from The National. Let’s go. You got Bon Iver on the track! Then she went back to Midnights, and I was pretty unimpressed with the first listen. Listen, I love the Karma song because it’s so silly. “Karma is the cat in my lap.” But I was bummed that she went back to that sound so quickly. 

Zac: I just want to say real quickly, I really like folklore and evermore, and I do agree that in terms of the songwriting level, it’s probably her most impressive. But I would be so miserable if she kept making music that sounded like that, because I don’t want to be subjected to, like more. B*yg*n*us discourse, you know what I mean? Like I’m so sick of that kind of thing. The aestheticization and commodification of “sad girl music”. Even as someone who at no point in my life would have been described as a sad girl, it rings as very cynical to me and it really bothers me that you can’t talk about, legitimately, well written albums like folklore and evermore without that being the thing that people go to.

Madison: Let’s talk about the Eras tour. This whole thing is what got the question of “what is the deal with Taylor Swift” in my mind months ago. Ticketmaster obviously  sucks, and things really got screwed up, but then all of a sudden people didn’t get Taylor Swift tickets, and now I’m seeing far too many tweets on the timeline saying  “Taylor would never do this to us.” “She is our friend and she cares about us.” “Don’t say negative things about Taylor, she wouldn’t want to see it.” All of this bizarre chatter. She is the world’s number one capitalistic pop star, on her own private jet. I just don’t understand where that attitude comes from or where people get these ideas from. 

Hope: It’s really fascinating me because I’ve been in different fandoms since I was 15. I’m not in any Taylor Swift fandom at all, but I’m on Tumblr and some people that I follow are very Taylor Swift oriented so I see behind the curtain sometimes. I  think it’s just because she and her team have cultivated such a genius way to show community with fans, whether it’s scouring social media or tour dates to send specific fans gifts, get them closer to the stage or commenting and liking posts on TikTok or on Tumblr. All the other stuff that she does, like the Easter eggs and the music videos, making people feel like a community and the listening parties that happened in 2014 where fans were invited to her house. There’s so much that all these fans have that makes it a parasocial relationship where they feel like they know her, even though it’s very one sided. Because people don’t really know anything about her. And I think there’s a lot of good that comes with that, like with community with fans and the closeness to an artist they wouldn’t feel otherwise. But I also feel like there’s  a darker undercurrent to that where they’ve created this illusion of closeness. So these people have a unique community. But then there’s aggression and entitlement. And uncomfortable worship in ways that happen when fandoms and artists get too close. And I see a lot of fans chasing clout or having a hunger for attention, especially on TikTok and Twitter. You see that a lot more than you do on Tumblr. There is a good side to it, like everyone’s outfits on the Eras tour, but then there’s a darker undercurrent with the community underneath it all. 

Madison: Great answer from somebody on the inside. The community did seem like it was great at the Eras Tour. I will say that once I saw it happening, I was having FOMO. This looks like it’s awesome. And both of you got to go, right?

Ryleigh: So my friend got us tickets and we just  got lucky in the lottery and we were able to get cheap tickets. Phoebe Bridgers came out and said, “This show is gonna change your life.” And I was like, what? And it was just, it was bananas, dude. There were little kids with their dads freaking out to “You Belong With Me,”  in costume. I don’t know, it was wild. Like, three and a half hours long. It’s an experience. The production level was insane, I walked away silent, and my biggest take away after a few days was that nobody should have that much power. It was startling. I’ve never seen such visceral emotion coming from people of all ages.

Hope: It was, it was unsettling. It’s not even a concert, it’s like an experience. 

Ryleigh: Yes, it was. It was amazing. During the show, I thought, I’m not gonna drink beer because I’m gonna have to go to the bathroom. And I just stood and experienced it. Yeah, nobody should have that much power though, not at all. And to be apolitical and not say things with that much power is what bums me. 

Hope: She does have white feminism. I feel like with our political climate too, you can’t be someone with a platform and not say anything right now. I feel like not saying anything is very complicit. 

Ryleigh: It might have worked before, in her earlier years, to be mysterious, apolitical. The second you get past a certain point of fame, you do not have the luxury to not say things anymore. She could have said to drink the kool-aid and everybody in the stadium would have done it. I think that in Chicago, she said something very bare bones like, “Go out and vote. This community is for everybody!” But what about Florida, though. What about Tennessee? Maybe show up in drag? It didn’t feel genuine, and that sucks.

Madison: I’ve always felt that way about her. I feel that way about celebrities, with large platforms in general. I understand that people really shouldn’t need to take advice from large pop stars. But I watched The Miss Americana documentary a few days ago and it said that when she finally did come out with her first political statement in 2018, she backed two Democrats in the Tennessee midterms. Within the next 24 hours, 65,000 people from 18 to 29 registered to vote. Which goes back to that nobody should have that much power. But if you do, and you know you do? And to not use it? That sucks.

Ryleigh: I didn’t know that. That statistic, that’s pretty gross. That sucks. What about your carbon footprint, Taylor? What about your jet, girl? Oh, my God. That’s insane. That is bananas. 

Madison: It feels frustrating because you have “You Need to Calm Down”, which was written and directed towards the LGBTQIA+ community, but it felt like pandering.

Hope: She never really spoke about it. She just did the song and video and moved on.

Madison: What is stopping her from pulling a Hayley Williams? And saying “Don’t vote for Ron DeSantis!” At least something a little in the middle of that and what you’re currently doing.

Ryleigh: Really, I mean having trans and queer representation in your music videos. Great, but yeah, it’s the fact that to my knowledge she didn’t say anything in Florida at all. 

Hope: No, I don’t think so. I think unfortunately, because she has two starkly different demographics that are her fan base, where she has people who want her to be more forward with her views, and then she has this very large, predominantly conservative,  white, right-wing group of women that also love her. So she panders a lot, she has her whole entire career and I think that’s like part of what it has to be now. She’s just a machine. You see that the Matty Healy relationship she had. She doesn’t want to make people mad. She doesn’t want to toe the line. Which she should! But I think it’s about the different demographics and playing to all of her fanbase.

Zac: I’ll be very quick – it is very frustrating to see the sort lip service in “You Need To Calm Down.” It’s enough about queer people that if you are a queer person you can say, OK, I like this, but it’s also not explicit enough that if you disagree with it, it’s going to offend you, which is frustrating. But I’m also of the opinion that  nobody who is at her level and has, you know, as much money and as much power as she does, pretty much by definition, is going to believe the correct things, so it doesn’t bother me too much to be honest. She made those cookies that said Joe and Kamala or whatever and that’s what you’re gonna get if you want her to say something. So it’s kind of like whatever to me. Now, if we’re talking about Laura Jane Grace, that’s a different story. 

Madison: That also does make sense. You’re right. Eat the rich. She is rich with her jet and her boat, and she probably doesn’t pay as much taxes as the rest of us do. We could easily talk about a bunch of other topics, but let’s wrap it here with final statements about Taylor Swift in general.

Hope: Throughout all of it, I  think there’s so much gray when looking at these multi-million dollar brands disguised as celebrities and musicians and that there’s so much else going on that it’s not just black and white. You’re going to get what they want you to get, and there’s a lot that goes down into their behavior, like the suits, the CEOs, the board meetings and then her. So I feel like there’s a lot going into the infrastructure of what Taylor Swift is. So that’s mine. Music rocks.  

Ryleigh: I think a lot of it for me, a lot of it is drenched in nostalgia. I will always have a relationship with that, similar to so many other bands, especially from the 2010s. I’m still into indie Taylor. I was hoping for indie Taylor Swift for a minute with the better lyrics, singing, and evocative feelings. It felt like it was working for her. But also, nobody should have that much power. This just might be my take away at the end of the day. 

Zac: I want my pop stars to make good pop music and to the extent that she makes good pop music, I will support her with my life and if she ever puts out another album like Reputation again, she is first. She’s the first course in the meal of eating the rich. 

Madison: I still feel kind of in the middle about her because she writes some bops. I mean, “Cruel Summer.” I listen to it every day when on my drive home and it’s great. But it’s really tough for me to like and support an artist a lot and not know a lot about them as a person, or not agree with their political views and what they’re saying and supporting publicly. The whole Ticketmaster thing and the bizarre fan relationships will continue to turn me off from ever being a full fucking Swiftie. I don’t know if I would ever go to a show,  even though it does seem amazing, because I feel like I would feel isolated from the community. But overall, she’s a much better songwriter and a better artist than people give her credit for. But at the end of the day, we do have to remember that she is really the Taylor Swift Machine and we don’t know her. None of you know her. Or anything about her life. 

Zac: Actually, I do know one thing about Taylor Swift, because she sent me a DM the other day and she told me that she actually does agree with everything that we’ve talked about and she is also actually a communist. And I don’t know if you know this, but Taylor Swift’s the same kind of communist that I am. And she told me that. And she also told me that she is gonna hang out with me and bake me cookies. That’s a joke.

Hope: Can she invite us to her NYC apartment? 

Madison: Can she retweet this article once it goes live? Can we get that promise from her? 

Hope: Her team won’t allow it. 

Zac: Taylor Swift read The Alternative challenge.

Hope Ankley | @Hope_ankleknee

Zac Djamoos | @gr8whitebison

Madison Van Houten | @madisonvanhalen

Ryleigh Wann | @wannderfullll

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