Is Taylor Swift’s Midnights Great or Cringe? Four Generations of Fans Debate.

To debate where Taylor Swift’s Midnights ranks among her albums, Slate assembled representatives from four generations of Swift fans: Slate music critic Carl Wilson, a Gen Xer; Slate executive editor Susan Matthews, a millennial (the generation most likely to be Swift fans, according to a recent Wall Street Journal/Ipsos poll); ICYMI host Rachelle Hampton, a zillennial; and Amity, a 10-year-old who requested we not use her real name. The result is the following conversation, which has been lightly condensed and edited for clarity.

Susan Matthews: Hi, fellow Swifties, a term I have never once used before, but am proud to use now for this occasion! That occasion is the release of Taylor Swift’s 10^th studio album. I would actually call myself a somewhat recent Taylor Swift convert—I basically started listening to her with 1989 (my birth year as well), and sunk ever deeper with subsequent albums. But I was really curious and maybe even a little bit nervous for her as the deadline of Midnights came closer—what could this artist do after her turn in Folklore and Evermore, two albums that, in my estimation, perfectly captured the moment. So I guess my first question is: How do you feel about this album? And how do you think it compares to her past work?

Carl Wilson: Hello all! I already expressed a lot of my thoughts about the record in my review on Friday. But I think in summary, the key to Midnights is that it’s a revisiting and reconsideration of many of Swift’s key themes of her albums ever since 1989, or at least Reputation, from a more mature and self-critical perspective. That’s what makes the title concept resonant: This is Taylor in the dark, over a bottle of wine, channeling the kinds of thoughts that nag at a person late in the evening. In some ways that makes it a less exciting record—I’d be hard-pressed to name any surprising new directions she takes here—but it’s a satisfying one for fans. On key songs such as “Anti-Hero,” “Question … ?”, “Mastermind,” and, among the bonus tracks, “Would’ve, Could’ve, Should’ve” and “Dear Reader,” we find her returning to stories that feel familiar, but with second thoughts. She interrogates her own agency, or sometimes (not always!) offers a more generous view of the other person’s feelings or motivations. To me, all of that makes it hard to rank it among her records. It has a fresh kind of steadiness, but at the same time, yes, maybe few of the songs hit as hard as their previous iterations.

Amity: I thought it was very good (some songs better than others), but I did think some albums for sure beat it. It was a good album but I did not think it was all I hoped for. I listened to the album for one day and then just listened to a couple of the songs. I would much rather listen to 1989, Lover, or Folklore over this.

Rachelle Hampton: To be completely honest, I was so unenthused about this album that I spent the weekend listening to Carly Rae Jepsen’s new album instead. When I finally got around to listening to Midnights in preparation for this chat, I feel like my reticence was validated in that it doesn’t compare to her best work, Folklore or Evermore. Unfortunately, Midnights is giving me Reputation and Lover vibes, two of my least favorite T-Swift albums.

Matthews: As soon as I turned it on last Friday (I did not stay up for it!), I was honestly relieved to hear that we were going back toward … a more 1989/Reputation zone! I am a huge Reputation defender (the back half in particular), and I felt like she hit the mark of moving out of the folk-y era and into something that feels more of the moment. I love the National as much as anyone, but I was ready for some pop.

Amity: I was excited for a pop album, too.

Matthews: Will also say that I am a big defender of the back half of Lover…

Amity: Agreed.

Hampton: We’re definitely in the dance album era, but I think other pop girlies do it better than Taylor. I’m a fan of 1989 and there are songs off Lover I really love, like “Death by a Thousand Cuts.”

Amity: I think Olivia Rodrigo is beating her now.

Wilson: What songs stand out as the strongest or weakest to all of you?

Matthews: Carl, I really agreed with what you wrote in your review, where you said “it may be the first non-Folklore-phase album Swift has made that has nothing notably bad on it at all.” I routinely start 1989 at “Blank Space,” to skip “Welcome to New York,” an atrocity. We do not need to get into “Me!” or the other failures on Lover and, I have to be honest, Reputation.

I am a real sucker for “Anti-Hero”—I think that is a real standout and I truly don’t understand it as Track 3 as opposed to Track 5.

Amity: Same! I thought that was the best of the album!

Matthews: I also really like “Midnight Rain,” “Question … ?”, and “Karma,” … plus “Sweet Nothing” and “Mastermind” are nice closers.

Hampton: “Sweet Nothing” stood out to me, as well as “Labyrinth.” I also liked “Lavender Haze.”

Wilson: I really think this is a case where she should have opened the album with the manifesto—if “Anti-Hero” were Track 1, it would really set up the album for listeners. “Lavender Haze” is a fine track, but the, well, haziness of that followed by “Maroon” makes it easy for the attention to wander.

Amity: I thought the music video for “Anti-Hero” was amazing, too. I thought that it also just showed the general flaws of life and past things bothering you.

Matthews: Yes, AND I will take this moment to defend the “sexy baby” line! I think the music video goes even further to underline the point, which is the feeling of just—ugh, why do I feel so gross right now? I think that line and the video is pure Taylor, distilling a feeling everyone has into a sharp little lyric that is certainly one part absurd, but it’s the relatability of it all that makes it so classic Taylor. Rachelle, I need to know what you think of “sexy baby,” is it cringe?

Hampton: Deeply cringe.

Wilson: Consider that “cringe” in context though—the “sexy baby” thought (besides being a funny 30 Rock reference) is the thought of an anti-hero. It’s Taylor confessing to her worst thoughts about the already-mentioned Olivia Rodrigo and all the other young pop women coming up behind her, how they make her feel old and, as she goes on to say, monstrous. I think we’re meant to understand that this is internalized misogyny talking in her head.

Amity: Also, this does bring up mentions of always needing to change and seem young and fresh.

Hampton: I definitely understand the intent behind the song, but I think she expresses the sentiment much better on “Nothing New” with Phoebe Bridgers. I think that song’s much more emotionally resonant without the cringe. Which also brings me to one of my eternal Taylor gripes: She is terrible at collaborations with women. “Nothing New” stands out as an exception, but Lana Del Rey is wasted on this album. As were the Chicks and HAIM on Folkeverloremore.

Matthews: Yes, agree with this, the Lana collab is totally fine but it should be … good? “Are the other women ever actually allowed to be present?” is the eternal Taylor question.

Hampton: It really stands out when you consider her work with Bon Iver and the National, or even Ed Sheeran and Gary Lightbody. Those collaborations feel like collaborations as opposed to a few backing “oohs” and “aahs.”

Amity: Yeah, they feel much more real and like they are really meant to be there.

Wilson: There’s a meld between Taylor and Lana’s voices on “Snow at the Beach” that’s musically beautiful, and I don’t know if LDR wrote any of the lines, but some of them seem like it. I really like the song overall but totally agree that it’s mysterious and frustrating that Taylor never gives her women guests any solo lines, especially after all the criticism in the past.

Matthews: Here is a question for you all: I was surprised that I ended up missing the obviously, intentionally fictional stories featured in Folklore and Evermore. At the time, I kind of found those cringe! But now, with Taylor in a relatively stable relationship, the autobiographical-ness feels like one of the problems. She isn’t making any art that is interesting about long-term relationships. (It’s all about comfort, being seen as yourself, and I don’t know, that’s nice and all, but there is no drama.) And I am also really sick of her making songs about the stories in her past that feel incredibly over-litigated to me. So … OK, this is where I will personally be a terribly cringe millennial: One of the songs that really bothers me on this album is “Vigilante Shit”? Like, when I hear anyone use the term vigilante now, I only think about like … the current political moment, Dobbs, “vigilante lawsuits,” etc. Should I even want Taylor to attempt to make political art? Probably not, but for some reason, I wondered if the next step for her is to move beyond the personal and into … the political? Help.

Amity: I think she just needs to find new kinds of stories. She is just talking about the same situations. Political songs or friend songs would be a nice refresh, maybe?

Matthews: Yeah, she should listen to Home Video by Lucy Dacus for some friend-album inspo.

Wilson: God, I think a political song is the last thing we should want from her. But as Susan said, she already took a step in this direction with the fictional narratives on the Folkermore records—which include some songs based on friends’ stories. I agree that there’s a bit of a regression here on that level—my question is whether she felt, going back to a more pop style, that she had to return to the old tried-and-true themes as well, or whether (as I hope) this is kind of a farewell to those stories in preparation for moving on elsewhere.

Hampton: There are … very few things I could think of that I want less than Taylor Swift writing a political anthem.

Matthews: Hahaha, OK, OK, fair, I regret asking if we need a political anthem from Taylor. But a song about how she feels about her turn to political engagement? Maybe?? I will forget ever saying this.

The other songs I really didn’t care that much for were “You’re On Your Own, Kid,” and “Bejeweled” (how she wrote that after also writing “Mirrorball” is a mystery for the ages).

Amity: To be honest I did not really like many of the bonus tracks.

Matthews: Agree that the bonus tracks are superfluous except “Would’ve, Could’ve, Should’ve.” Feels like it is time to talk about “Karma,” which seems to be another controversial song …

Amity: I also think we should bring up “Karma.” I have been very on the fence about it. I at first did think it was cringe. But it has grown on me.

Matthews: I am pro-“Karma.” It is the kind of Taylor song that will become canon once we get used to it, I think.

Wilson: “Karma” is growing on me, too. “Would’ve, Could’ve, Should’ve” is a killer, literally. A slash and burn version of her past romantic revenge songs, but one where she stays inside the house as it burns. And I think “Dear Reader” has a really lovely coda to it, about Taylor not wanting to be seen as a role model or giver of wisdom. However, the other five bonus tracks really get in the way. Somebody should be around to tell her enough is enough. (This is also true about some of her lyrics, which could very much use an editor these days.)

Amity: I think the bonus tracks have added a bit of a “quantity over quality” feel.

Hampton: I almost feel like “Would’ve, Could’ve, Should’ve” … should’ve been on the main album?

Wilson: Before we get to the end, I’d like to hear what people think about the sound of this album. Are you pro- or anti-Antonoff? How does the music work for you? I also think it’s one of her best albums vocally, continuing the growth she made there on the previous two albums.

Matthews: In terms of the sound of the album, to me, it feels like the right combination of warm, flirty, and just the right amount of grit—that’s what I mean when I say that it reminds me of the best parts of 1989, Lover, and Reputation. I know that people who actually understand music better than I do have strong feelings about Antonoff, but to me, the relief of this album is that it’s something that I will listen to while running errands, while the pandemic albums are going to be ones that I Listen To when I want to be in that emotional place. This is accessible in the Taylor way. It’s not particularly groundbreaking, but it makes me feel fuzzy in the right ways. And that is really what I am looking for from Taylor—I have other artists for … everything else!

Hampton: I’m not sure how much of a compliment “music to listen to in the background” is, but I agree with you, Susan, in that that’s most likely how I’ll be listening to Midnights in the future. But I think the draw of Swift, for me, is her ability to get to that emotional place. That’s where I find her the most compelling. There are other artists (like Carly!) who, to me, capture that warm, flirty vibe in a way that actually gets me to come back to an album.

Wilson: Our editor has noted that across the panel—Gen-X me down to Gen-Z Amity—it seems like our opinions of Midnights get more positive or perhaps more forgiving the older we are? I know I tend to follow Taylor more as the journey of a songwriter who I want to see get to her best potential (and get as free as possible of the damage done by being a teen star, etc.)—and on other levels the stakes don’t feel personally high to me. What do you think about the ways she’s reaching audiences generationally, or perhaps failing to do so, at this point in her career?

Amity: I think she has been under pressure, but I think now it has changed based on age and popularity. I think she is losing some motivation. Her life is good, and she is in a good relationship, and has a nice smaller but big crowd of fans supporting her, so she is not under the same struggle.

Matthews: I think the best thing that Taylor can do is to accept that she is not going to be everything to everyone. And to some degree, that’s why I found the Folklore/Evermore aside to be so fascinating—it felt like something she was doing, and she knew that maybe it wouldn’t be quite as universal. It turned out that it basically was, anyway, but I think what I’d like to watch her do now is really narrow in on different stories or themes that might be less broad. Maybe that is not the Taylor Swift Project, but it is what I want for her.

Wilson: I think you’re right, Susan. That stage of shifting from being a dominant top-of-the-charts star to a more midcareer album artist, still famous but more in your own niche, is a tricky thing for a lot of artists to navigate once they are in their 30s.

Hampton: In a lot of ways, Taylor Swift reads to me as an extremely millennial avatar, and I say that as a zillennial. She’s been caught between a lot of shifting dynamics, politically and socially. She’s been held up as either a feminist icon or peak white womanhood or a silly girl. I think you can see her trying to work through how she feels about all of that, work through what a lot of millennial women are working through, which is the knowledge that you can’t actually have or be it all. And ultimately, yeah, I think her downfall is when she, as Susan said, tries to be everything to everyone.