I commented on the Barbie movie, so I guess I’m also obligated to comment on Taylor Swift too, right?

I thought this article was very interesting and insightful. Like Hemingway, I am a Gen Xer, though his knowledge of more recent pop culture definitely exceeds mine. My knowledge of pop culture peters out pretty quickly after about 1991. I probably know more pop culture from the 20 years before I was born than I do the last twenty years.  
Anyway, Hemingway’s article makes three points that I think are worth considering. 
First, he is right that we have lost a shared pop culture, which means we have lost a source of community. Of course, the pop culture we did share, before the rise of the internet shattered the music industry, was pretty trashy in many ways. But things have only gotten worse, as pop stars, movie makers, etc. continue to push the envelope and transgress boundaries. The loss of a shared pop culture, even a relatively immature pop culture, represents the loss of shared experiences and social cohesion; it adds to our feeling of loneliness and isolation in an already polarized culture. I agree with Hemingway that Tom Petty was one of the last of great icons of pop culture who seemed to have really wide appeal. And I would add, he also did the best Super Bowl halftime show I can recall. Today, Taylor Swift would be the closest figure we have to a pop culture icon. Like the Beatles, everyone knows her and recognizes her music, whether they love her or hate her. She has crossed genres and (as Hemingway points out) is adored by the masses and critics alike. That’s very rare today — and it only serves to reinforce her popularity all the more. If people use pop culture to connect as much as to be entertained, Swift is about your only option today. There is no doubt about it: Swift has created a community around herself. Love abounds not just for her music, but for Swift herself, for what she represents. Swift fandom has become a bond that ties many together in an almost quasi-religious way. And as critics of Swift have often discovered, her fanbase is intensely loyal and will come to her defense. Hemingway’s summary is exactly right in how he assesses the change in culture and the current appeal of Swift:
The best pop stars simply transcend pedestrian political concerns, explaining Swift’s appeal doesn’t have to be done through the lens of feminism. Six years ago — long before, say, the Dobbs decision or the New Right writing essays about “The Longhouse” — I observed after Tom Petty’s death, “a huge swath of America, across beliefs, cultures, generations, and races, would want to claim Tom Petty’s music and feel some solidarity in his loss. We need unifying cultural figures and artists now more than ever.” Petty was obviously very masculine and a baby boomer, but his massive appeal over several decades — at the time of his death, one out of every 40 songs played on classic rock radio was Tom Petty — and Swift’s appeal are both born of a universal desire for human connection.
All this to say: Swift has become a kind of symbol for our culture in this age. She is, as Mary Harrington has said, a phenomenon. She is a style — even a lifestyle. She is a culture — the very sum and substance of pop culture in this moment. She is more than the sum of her parts; she stands for a whole package of trends and fads. But more than that, she is the iconic representative of (post)modern life. 
Second, I think Hemingway has a point about Swift’s narcissism. Sure, the 70s was the “me generation” — but it seems every generation since has gotten even more self-absorbed. Not surprisingly, the result of this self-absorption is relationship dysfunction and mental illness. Swft’s narcissism is especially seen in what has become her staple — the angry break up song. (I hope someone has warned Travis Kelce — he best go ahead and prepare himself to be the theme of a future song.) Now, I would not be the first to say that only a fool would look to pop stars of any era for relationship advice. It is proverbial that pop stars usually have very messy, complicated, and utterly depraved private lives. There a few exceptions to that rule, but not many. So no one should be expecting a sensible or wise view of love, sex, dating, or marriage to come out of pop music, whether from the 1960s or the 2020s. Nevertheless, there has been a shift for the worse, and the genre of break-up songs is a good test case to demonstrate that. I'm tempted to go all the way back to the Hank Williams era and consider a classic like his "I'm So Lonesome i Could Cry." But it isn't fair to compare any modern singer to Hank. So instead, take a few break-up songs from the 1970s and 80s. Think of something like “Silver Springs” by Fleetwood Mac or “Wasted Time” by the Eagles, or “The Heart of the Matter” by Don Henley, and compare them to Swift’s typical break up song. The older songs were more honest about the pain and — dare I say it? — they are often humble in the face of a failed relationship. The break up was an opportunity for self-reflection, forgiveness, and perhaps even a kind of change going forward. Not so with Swift. Her break up songs are (usually) bitter, vengeful, and spiteful. There is no room for self-reflection, only blaming the male. Her break-up songs are often less about heartbreak and more about how to get even. Whereas the older songs at least aspired to a permanent relationship, even if they lacked the maturity and skill to pull it off, that’s not the case with many of Swift’s relationship songs. Swift seems to expect her relationships to fail as soon as they start; indeed that is part of their attraction. They are doomed from the outset, so their only purpose seems to be the thrill of the moment. Many of Swift’s songs do not even seem to long for “happily ever after;” they are focused the fleeting experience of infatuation rather then permanence of true love, so the expectation of eventual disaster is casting its shadow over the couple all along the way. Relationships are treated as completely disposable. (I suppose her song “Love Story” is a shining exception, but that was a long time ago. I’m hardly familiar with her whole catalog of music, but others who know it better seem to agree with this assessment — namely that Swift’s music features “a craving for romantic transcendence that’s difficult to distinguish from self-destruction".) Again, Hemingway gives a good summation of all this:

Ironically enough, Tom Wolfe coined the phrase “the Me decade” to refer to the 1970s when artists such as Tom Petty rose to stardom. The idea was Americans were starting to move away from having an identity rooted in community and moving toward atomization — and certainly, a big part of that development was the ability for individuals to find meaning outside local communities and identify with distant pop culture figures whose identity and branding were created by relatively new mass media technologies.

But this development, however startling it was to astute critics such as Wolfe, was embryonic 50 years ago. With Taylor Swift we see it in full flower; maybe it took 30-some years, but the cultural trends that emerged from the ’70s finally produced an artist almost wholly dedicated to “Me Music.” This finally brings me to my actual gripe, the specifics of why and how her music sucks: It’s utterly defined by self-obsession rather than introspection. Where other artists will occasionally do a Christmas album, it seems like every Taylor Swift album is a Festivus record devoted to the airing of grievances and feats of artistic strength.

To that end, she has almost wholly pioneered a new genre of what an acquaintance of mine calls the “bellyaching about a boyfriend” song. It’s true that young men are frequently terrible to young women and there’s nothing inherently wrong with this being fodder for pop songs, but there are limits. There’s yet another song on her latest record bashing one of her famous exes, John Mayer, following up on her infamous breakup song “Dear John” in 2010. Look, everyone knows Mayer was a terrible womanizer — but this was known before he dated her — and that was 14 YEARS AGO. Whether he’s fully atoned or not, the guy has since gotten sober and moved to Montana or whatever. It’s, as the kids say, pretty cringe to still be exploiting these past relationships, which considering Swift’s had a charmed life since she was a teenager, seem like pretty hollow examples of genuine heartbreak.

Perhaps Swift has longings for marriage and children. If so, they rarely make their way into her music, and it’s certainly not what she has become known for and her chosen lifestyle does really reflect those priorities. Yes, there have been angry break up songs in both rock and country genres in the past. But I don’t know of any singer as dedicated to this particular sub-genre as Swift. It has become her "thing."
Third, I think Hemingway is generally right about Swift’s appeal. I will not deny her talent. Yes, her lyrics are usually vapid, but her music is often catchy. Those who are looking for something deeper do not really understand the point of pop culture. The whole point of the enterprise is to subordinate artistry to money-making; and to make money, the product needs to be easily accessible by the masses, must have a built in obsolescence, etc. Swift is the master of pop culture. She is the very embodiment and perfection of pop culture. In today's world, she is pop culture.
But all to say, however talented Swift might be as singer and songwriter, her real talent is not in music but in marketing. Drama sells, and Swift certainly surrounds herself with drama. What Swift has done is turn herself into a comprehensive brand. This has been good for her — she rakes in millions and millions — but bad for the culture in general since what she is really selling (especially to young girls/women) is a comprehensive way of looking at life and living in relationships. Her appeal cannot be separated from her danger. She is an icon for her lifestyle, embedded in, but going far beyond, her music. Again, Hemingway nails it:
[G]iven her popularity in the face of this lyrical obsession, it’s a chicken-or-egg-first proposition about whether the cultural avatar of millennial females is famous for being near constantly romantically aggrieved even as TikTok is full of videos of women insisting, “No really, it’s great being 29 and unmarried and childless, I don’t want that at all, I get to sleep in on weekends and learn to make shakshuka, this is the most fulfilling life I can conceive of, I’M HAPPY WHY WON’T ANYONE BELIEVE ME?!” 

Hemingway notes that Swift’s development — as an artist, and perhaps also as a person — is stunted. (Candace Owens has made the same point, also citing Swift's pettiness in how she treats her exes as proof.) Like many artists, much of what she writes arises out of pain and brokenness, but somehow one gets the sense with Swift that her relationships, like her songs about them, are largely performative rather than substantive. Even compared to the banal pop culture of my youth, her music and lyrics are remarkably immature and unsophisticated:

Swift is 33 years old, has 10 studio albums under her belt, and has limitless resources to pursue her artistic vision. Anyone want to make a case that her body of work evinces a great deal of artistic exploration and emotional growth over the course of her career?…

[A] big part of the problem is that Swift is very, very good at serving an audience that has been conditioned to accept less in terms of musical and lyrical sophistication. Look, you can choose to like Taylor Swift, and I concede she’s so good at the exact thing she does that she’s hard to resist in certain contexts. If the occasional three-minute bursts of Swift make you feel good, I won’t deny you that.  

However, the over-the-top celebration of Swift’s success says volumes about the stagnation of pop culture. At some point, we have to recognize that even if you embrace the limits of pop music, the distance between middlebrow entertainment and the lowest common denominator is enormous. Our need for shared artistic connection cannot be allowed to overwhelm a duty to also collectively seek out music that takes us places and challenges us with insights into the human condition, revelations about ourselves we didn’t know (or maybe didn’t want to know), and otherwise produces insights into the problems of others. And I, for one, already know enough to know Taylor Swift just doesn’t have it in her to do that.

Since Swift sings many songs about her personal relationships, one wonders what turn her music might take if she settled down with a husband, had a few kids, and kept writing and singing songs as a side gig. Alas, that does not seem likely to happen anytime soon.
It seems Swift is stuck, singing the same song over and over about one failed relationship after another. She keeps reinventing herself, but she never gets anywhere; thus, in every “era” she ends up with the same result. In this way she has become not merely a pop culture icon, but an icon for the modern image of womanhood — successful at making money, a failure when it comes to relationships (and the family life that flows out of those relationships). In a culture that is seeing marriage rates and birth rates plummet, a culture that is seeing female misery explode, Swift is both cause and effect — she reflects the deepest dysfunctionalities of our culture and also reinforces them. My hope is that one of these days Swift will fall in love with someone other than herself.