The Worst Thing You Ever Heard — on pop songs, being 'in your feelings,' and cruel summers

I recently asked my co-worker, Andrea, if she had heard the new Taylor Swift single, “Cruel Summer”—not because Andrea is a Taylor Swift fan, or even a fan of ‘pop music.’ I asked because of Annie Clarke’s association with the song—credited as a co-writer in the album’s liner notes.

Andrea was, at one time, and still is to some extent, a fan of St. Vincent.

She was not aware of Clarke’s involvement with “Cruel Summer,” and proceeded to tell me she didn’t really have an opinion on Swift’s music, one way or the other.

I told her the song was good; alarmingly good, and that she should give it a listen.

After asking maybe one other time if she had listened (she still hadn’t), I texted a link to the song’s YouTube ‘Official Audio’ video, hoping she would humor me.

“May or may not have made me dance…just a bit,” Andrea texted me back after she finished listening. Then, after another three minutes (the duration of the song) had passed, “I totally listened a second time.”

Roughly five minutes later, “Um, I think it might be my new jam?”


Since her arrival in the late 2000s—I want to say that, much like my co-worker, I haven’t had an opinion on Swift’s music, one way or the other.

But that isn’t true.

Five years ago, both out of the hype surrounding it and out of my own morbid curiosity, I listened to Swift’s fifth album and first as a true pop star, 1989—reviewing it, and more or less panning it, writing it off a little too haughtily as disposable product (except for “Wildest Dreams,” which I legitimately enjoyed at the time.)

A year later, I, like so many others (white men, mostly) fell under the spell cast by Ryan Adams, who ‘mansplained1989, claiming that Swift’s original helped him while he was separating from his wife at the time, Mandy Moore, and because of how much the album meant to him, he recorded and released a song by song cover album of it—dramatically reinterpreting Swift’s pop songs.

I knew Taylor Swift as the frizzy haired blonde, clutching an acoustic guitar, who slowly, gradually, began making her ascent from simply being a teenage country music singer, to being embraced by ‘pop’ music as a whole.

I knew Taylor Swift from her 2009 acceptance speech being interrupted by a very drunk, leather clad Kanye West, at the MTV Video Music Awards, when he told her he was really happy she had won and was going to let her finish, but that Beyonce’s “Single Ladies” was the best video of all time.

Swift later, in 2015, introduced West when he won the Video Vanguard Award at the same award show; he returned the favor only a few months later by referencing her in a ribald lyric on “Famous,” from The Life of Pablo.2

I knew that at some point, maybe even soon after it was released, Swift’s fourth album, Red, had been named a part of the pop canon—the vinyl edition gracing the turntable of a very hard to please, opinionated ‘music friend’ of mine, and it recently earning a very generous 9+ review from Pitchfork when they did a retrospective on her previous albums, leading up to the release of her most recent effort, Lover.

I knew that the two singles released in advance of Lover, the Technicolor “ME!” featuring Brendon Urie of Panic At The Disco, and the cumbersomely titled “You Need to Calm Down,” had been received well commercially, but were perplexing to critics.

And truthfully, I had not really planned on paying much attention at all to new album from Taylor Swift—but after Lover arrived on the internet a day before its release, there was a palpable buzz about a number of songs from it, including the album’s second track, “Cruel Summer,” co-written by Swift, Annie Clarke, and Swift’s go-to pop music impresario Jack Antonoff.


My co-worker Wesley lives and dies by his Google Music algorithm, or as I have taken to calling it, the ‘algoriddim.’

Or has he has taken to calling it, the ‘Google doodab.’

Wesley was a guest on the Anhedonic Headphones podcast, where we talked a lot about Better Than Ezra’s “Desperately Wanting,” and the time he saw them at a county fair when he was still living in Missouri, but more importantly, I learned that he doesn’t listen to albums—he is more song oriented, partially because of the line of work he’s been in for a majority of his life.

He’s the assistant manager of the deli, and you can’t just stop prepping a dish because an album has come to an end, and then put something else on; the songs have to keep coming—and that’s what he’s used the algorithm for.

As a whole, I am an album oriented listener, but am able to appreciate a song, or a single, on its own, and recently I’ve learned that Wesley has become rather impressed with what a song, on its own, can do for—and do to—a listener.

One of the pre-set stations on his ‘Google doodab’ is “Kiss Me” Radio—the station always begins with “Kiss Me,” the ubiquitous slice of pop music from Sixpence None The Richer. I don’t even recall how, or why, this song came up originally in the algorithm, but we have often discussed the nostalgia for the late 1990s that it brings up, and that while yes, lyrically, it may be slightly on the insipid side, I’ve realized now as an adult what I failed to realize as a teenager—that it’s a good pop song.

“Kiss Me” Radio, much like any streaming radio service assembled through an algorithm, has provided Wesley, and whoever else happens to be in the kitchen at the time, with some similarly minded songs, as well as some questionable and perplexing choices.

A few weeks ago, I was wandering by the kitchen when I was stopped in my tracks as I heard the sound of something familiar coming from the stereo.

It’s a song that I hadn’t thought about in a very, very long time, and as I caught it at just the right moment, with the infectious refrain exploding, I more or less burst into the kitchen, both of my hands in the air, doing a dance move that involves a lot of pointing on my part, singing along with reckless abandon.

The song, released 15 years prior, was “Pieces of Me,” by Ashlee Simpson3, which I proceeded to declare an absolute banger, much to the disbelief of Wesley, who was visibly confused, and possibly uncomfortable, by the events unfolding around him.

I continued, once the excitement from hearing the refrain had died down, by telling Wesley that the song came out in the summer of 2004—the summer before my final year in college, and that it, in a way, it was a song that meant something to me because at the time, as I put it, I was “going through some things.”

I think I may have also used the expression, “I was in my feelings.”

It took Wesley maybe one or two more listens in subsequent days where we were working together for him to come around on “Pieces of Me,” eventually admitting that it’s a really good pop song, which is why I tried to push things further in the kitchen by asking him if he had heard “Cruel Summer.”

He humored me by calling it up on his Google doodab, giving me a sideways glance and asking if it was a cover—the second time that question had been asked of me, w/r/t this song, in 24 hours4. He hit play, and even with “Cruel Summer”’s enormous refrain—the kind of refrain that hits and the only thing you can do is throw your hands up in the air and do some kind of white person dance move that involves a lot of pointing, singing along—Wesley, much to my disappointment, was nonplussed by the song.

He quickly changed the station on his phone—“Cruel Summer” Radio was going to open a deluge of other Top 40 pop music neither of us were ready for, and as he did that, I excitedly told him that I thought the song was my summertime jam of 2019.

Without even missing a beat, Wesley looked me in the eyes, telling me in a low, serious voice, “Kevin, summer is almost over.”5


“Cruel Summer” is sequenced second in what is, in today’s marketplace, an extraordinarily long album. Lover is 18 tracks deep, arriving at over an hour; it’s two advance singles are buried well into the latter half, not so much as a bait and switch, or to make people forget that these songs were released ahead of the album, but to make listeners understand that there is a lot going on here.

Lover is almost intimidating, just because 18 tracks is, like, a lot of songs, and over an hour of pop music (some of which is of diminishing returns) is a lot to ask of somebody who is, by all accounts, not that much of a fan of Swift in the first place—or, at the very least, hasn’t bothered to form a real opinion of her canon.

Placing a song as good as “Cruel Summer” so early in the record is audacious. It makes up for the awkward misstep of “I Forgot That You Existed,” which serves as the album’s opening track, and it also is a tough act to follow. There are lot of songs on Lover that are not as well executed, and there are a lot that are surprisingly fun and listenable.

There is, like, a pretty unbelievable run of songs, beginning with “I Think He Knows,” and ending with “Cornelia Street” that is surprisingly impressive.

But nothing comes this close.

“Cruel Summer” works in only the way a near perfect pop song can work—it’s in the way its structured, built around low, simmering verses where Swift’s voice slithers and slinks in between glitchy, skittering, and bubbling synthesizers, until the whole thing explodes in the refrain, because that’s the point of a pop song—something huge that makes you reach for the volume button on your radio, so you can belt it out in the car when it comes on.

The hook, or refrain, or whatever you want to call it, is what people remember—or what people will remember, but in a song that is, hands down, as good as “Cruel Summer” is capable of being, the verses, as well as the song’s incredible bridge section, are equally, and in some cases more important.


It has almost become satirical at this point, but outside of her music, the one thing Swift may be known for even more is her very public relationships—the joke, often being, that every man that she’s reportedly linked to is going to wind up the subject of at least one song, at some point, in the future.

“Cruel Summer,” as is a bulk of Lover, is about her three-year relationship with British actor Joe Alwyn, who, as of this writing, is her current partner. While the song’s lyrics have not been officially annotated on Genius, there are a number of theories surrounding the song’s surprisingly evocative imagery. The only comment Swift herself has made on the song itself is that she wanted it to sound like a ‘desperate summer love that was doomed from the start,’ and that her favorite lyric in the song arrives at the end of the bridge section—“I love you. Ain’t that the worst thing you ever heard?”

The line between fact and fiction within a pop song like this is a tough one to navigate. How much of this torrid love affair described actually occurred throughout a summer of Swift’s life; how much of it is dramatized for effect; and how much of it is a constructed narrative used to get the song from one point to the next?

In the end, it truthfully doesn’t matter. The listener will find as much truth in the song as they want—or they’ll read it like they would a novel. Swift, and in this case, Antonoff and Annie Clarke, are both songwriters and storytellers, using the verses and refrain to craft vignettes, or moments, brimming with vivid, robust images.

It’s in the song’s second verse where that kind of storytelling really begins to take shape, and Swift, even through what seems like the use of simple phrasing, manages to conjure an expressive portrait of the tumult that is young love—or, love, in general.

“Hang your head low in the glow of the vending machine—I’m not dying,” she sings in a low register. “We say that we’ll just screw it up in these trying times—we’re not trying.”

It’s in what is referred to as the ‘pre-chorus,’ that she also continues with the expressions that walk an incredibly thin line between being totally cloying and borderline cliché, and fascinatingly emotional and relatable. “…Summer’s a knife and I’m always waiting for you just to cut to the bone,” she says, before adding right before the refrain slides in, “If I bleed, you’ll be the last to know.”


Then, there’s that refrain. That chorus. The hook. Whatever you want to call it.

They’re always big—they have to be, in a pop song, don’t they? The refrain? It has to be enormous—more than likely the thing that a songwriter starts with is that idea, then works it out both backwards and forwards, hoping the verses come together and that they’ve earned6 that moment.

There’s a part where much of the instrumentation drops out, for like a split second, before the refrain kicks in—“It’s new—the shape of your body. It’s blue—the feeling I’ve got,” Swift sings, and it’s a stark, surprisingly complicated juxtaposition to be found in a pop song. The startle that comes from embracing a new partner for the first time, or during those early intimate moments is one thing, and it’s sharply contrasted with a frank statement of melancholy, tinged with haunting regret.

“It’s cool, that’s what I tell ‘em. No rules in breakable heaven,” she continues the second, maybe slightly less impactful portion of the song’s refrain. “It’s a cruel summer with you.”

The thing about “Cruel Summer,” and why it works so well as an energetic, mesmerizing pop song, is the way the song’s second use of the refrain slides almost effortlessly into a bridge, and it’s in the bridge section where the song’s penchant for very visual drama—invented, or real, or both—thrives to a visceral level.

There is a fair amount of self-referential, recurring images and themes throughout both Swift’s latter day canon, as well as within Lover itself as a self-contained collection of songs. The idea of sadness, or being ‘blue,’ as well as the religious imagery of angels, devils, and heaven (whatever ‘breakable heaven’ is), and conceding to the fact that you’ve had too much to drink and are very much in your feelings, are things that are mentioned, at least according to Genius, within other Swift songs, but they are especially prevalent ideas on Lover.

Swift maybe an American Sweetheart of sorts but she’s also not afraid to put it out there—“I’m drunk in the back of the car, and I cried like a baby coming home from the bar,” she confesses without apology during the bridge of “Cruel Summer.” “Said ‘I’m fine,’ but it wasn’t true—I don’t wanna keep secrets to just to keep you.”

She continues, growing more emotional and unraveled—“I snuck in through the garden gate every night that summer just to seal my fate, and I scream, ‘For whatever it’s worth, I love you—ain’t that the worst thing you ever heard?’”

I guess it’s in that moment that the song, which is, from beginning to end, a fun and energetic pop song—it becomes something else. It becomes slightly more desperate; maybe a little more manic. It reveals how fragile—how ‘in her feelings’ the protagonist of the song really is, how cruel the summer really has been, and where the lines of being ‘in love’ and ‘love’ become blurred until they are difficult to distinguish.

It’s a huge moment—that part of the song. It’s a bit moment for Swift, as the protagonist, within the song’s narrative. And she goes for it—she makes it look effortless, to stand outside somebody’s window and scream at them about love.


I’m surprised by how quickly Andrea latches on to “Cruel Summer.”

In talking about the song one afternoon, she said it’s a bit of a flex on Swift’s part to release a summer song so late into the season—the album itself arrived on August 23rd, with roughly a month left before the first day of Autumn.

Later, Andrea tells me the song has a cathartic effect on her—something, that, I suppose all good, or well-executed pop music, can do to its listeners. It’s not something that happens to me all that often, so when I can feel that kind of release coming as the result of a pop song, I know that it’s something special.

I think about pop music as a form of escapism—it, as a whole, doesn’t ask a lot of its audience in return. It doesn’t ask a lot of difficult questions that maybe can’t be answered. The average pop song, by a pop singer, is here to entertain; to be, at the end of the day, ‘fun.’ This is the same reason why specific movies are financially successful, or why audiences turn on their televisions week after week to watch things like “The Bachelor.”

Taylor Swift, as a singer and songwriter, is an ‘entertainer.’ And even though Lover is an album full of fun, infectious songs—“Cruel Summer” being one of them—occasionally, even when you have, perhaps unknowingly, sought out a form of escapism, there’s a part of you that is unable to escape completely. You don’t ‘see yourself’ in the song—no, not exactly, but in the way it rebuffs your attempt at escapism, and the way you find yourself connecting to the song, and back in your own head despite your best efforts, is completely unexpected.

Even with telling me of the catharsis she felt, I’m equally, if not more, as surprised by how quickly Andrea burns herself out on “Cruel Summer,” apparently having listened to it entirely too many times in the car to and from work, or on a longer commute up to the Twin Cities.

She and I wonder what the shelf life of a song like “Cruel Summer,” at a time of year like this, is. Part of me wants to argue that it isn’t ‘timeless,’ but that is something that could still be enjoyed or appreciated—maybe not into the fall or winter, but it could be dusted off again next summer.

“Isn’t that the point of music like this?” Andrea contends. “To just listen to it a bunch, over and over again, and then move onto something else?”


Who decides the shelf life of a pop song? Is it the artist—is it in the intention when a song is written, recorded, and released, that it will only live on for a few, beautiful, invigorating, evocative moments before it all flickers out?

Is it the audience; or the listener—even the casual listener, such as myself, who latched onto one song out of 18, bestowing the title of “Summertime Jam 2019” unto it? The song lives on as a file on my hard drive, or a CD-R in the car of a friend, but how often is it revisited after summer has gone, the cool air comes through, and the leaves begin to turn and spiral to the ground?

There are people who always lament how quickly the summer passes—the chatter you hear from those who, come late August, ‘can’t believe how quickly the summer went.’ You rarely hear this about other seasons—the opposite, in fact, when it comes to the winter.

The summer months pass by just the same as the other seasons, but there’s a feeling associated with the warmer, longer days, that makes you want them to last more than they are willing to—and it makes those days easier to return to in memories.

The expression ‘Cruel Summer’ isn’t new—originating in the early 1980s with the Bananarama song of the same name, then being used in 2012 as the title of an often-forgot G.O.O.D Music compilation, curated by Kanye West.7 I’ve never thought of the summer as being particularly cruel before, but it can be—it can be as cruel, if not worse, than any other season.

Maybe, 15 years ago, when I was a college student heading into my final year, with a soft spot for the kind of pop song Ashlee Simpson’s “Piece of Me” was, I was in a cruel summer.

Maybe now, I’m coming to the end of another cruel summer—and maybe the cruelest part of all is that this song, sure, is capable of being both fun and cathartic, but here’s the thing—CD-Rs wear out, files get corrupted or are deleted, and songs fade from the zeitgeist almost as soon as they arrive, but we’re still left with the memories—and those confusing, ‘blue’ feelings and the visceral need to scream at somebody about love that Swift describes aren’t as easily forgotten.

Is that the worst thing you ever heard?

1 – The short version is that in February, Ryan Adams was outed as being a serial sexual abuser through a New York Times piece that citied Moore, and a handful of other women who he had preyed on throughout his career. I never believed Ryan Adams was, like, a good person deep down, but this news had made it impossible to listen to his music.

2- “I feel like me and Taylor might still have sex—I made that bitch famous.”

3 – It’s worth mentioning that following my conversation with Wesley about “Pieces of Me,” I asked him if he thought I should write some kind of thinkpiece about it. I don’t remember how the exchange we had exactly went, but at some point, I told him that what I do isn’t special, and that anybody could write a thinkpiece, which he took as a personal challenge, and did. It started out as a hitpiece on me, but then, as they always do, turned out to be a lot of other things too, and it’s really good.

4- I played this song for my wife who was incredibly unimpressed with it while she listened—she had asked if it was a cover of the Bananarama song, and then proceeded to play that video for me instead. It was weird, in the way that only a video from the early 1980s can be.

5- There are times when people I work with make me laugh a lot harder than I usually do in life. Wesley’s reflexive, earnest answer actually caused me to fall to the ground in a fit of laughter.

6- I don’t talk a lot about my ‘writing process,’ especially with music writing, which seems pretty straightforward, but rarely is, especially when I do audacious things like write 3,500 word essays about one Taylor Swift single. But, like, when I do write personal essays, long reads, et. al, I usually know how I want to begin, and I usually know how—sometimes right down to the very final line—I want it to end. It’s the middle, working myself back and forth between those two points, that I struggle with, and hope that by the time I’ve reached an ‘ending,’ I hope it is one that I’ve earned.

7- There was minor speculation that, when the Lover tracklist was revealed, the song “Cruel Summer” was going to be about West, as a direct reference to this compilation (G.O.O.D. Music is his vanity imprint, distributed through Def Jam.)