It’s Song of Summer season, and if Lil Nas X has anything to say about it, the battle for Song of Summer 2019 is already over. Despite a flashy new single (and imminent flashy new album) from Taylor Swift—plus new music, released Friday, from Miley Cyrus and Katy Perry—“Old Town Road” looks invincible, and its disruptive joys have pop stars, even relatively young ones, looking awfully musty and flat-footed. Are some of our biggest and boldest hitmakers ill-equipped for these times, or is renewed dominance just one hit song with Zedd (or Ghostface Killah, or the guy from Panic! At the Disco) away? Here, Ringer pop critics Lindsay Zoladz and Rob Harvilla chew over what’s eating some of the biggest artists in the world.

Rob Harvilla: The pop stars are struggling, Lindsay. They sound concerned. I am concerned. Taylor Swift’s aggressively vapid new single “ME!”, released in late April with a Godzilla-sized pastel shrug, has been denied her customary no. 1 spot by the ungodly colossus that is Lil Nas X’s “Old Town Road,” which has now been the biggest song in America for nine straight weeks. On Friday, Katy Perry served up “Never Really Over,” a medium bop that nonetheless can’t quite wash the taste of her wayward last album, 2017’s Witness, out of our mouths. Also, Miley Cyrus released a terrible EP called She Is Coming, a bawdy and knuckleheaded affair that features a Ghostface Killah collaboration called “D.R.E.A.M.,” in which the D stands for “drugs.” She sounds tired. I am tired.

And so, as we stumble into the direct sunlight of summer 2019, the boldface-pop-star slate looks awfully crowded—Rihanna is looming, thank God—but it seems awfully likely that none of these people have a prayer of unseating “Old Town Road,” on the charts or in our hearts. (Even early May’s “I Don’t Care,” a half-decent bro anthem delivered by Ed Sheeran and Justin Bieber, can’t compete on this bonkers new playing field.) Are Taylor, Katy, and Miley all just navigating personal artistic low points, or is their particular brand of pop supremacy under existential threat? Is there any song on She Is Coming that you ever want to hear again? And will “Old Town Road” still be no. 1 on Labor Day?

Lindsay Zoladz: Never really over indeed, Rob. Katy, Miley, and Taylor are all back, to varying degrees of John Wickian convincingness. I heartily agree with your assessment of Katy Perry’s new single as a “medium bop”—that it is not a disaster feels like a triumph in and of itself. Both Katy and producer Zedd are playing it safe here, updating what’s worked best for them in the past: Perry has traded in her vague political messaging for the sweeping yearning of, say, Teenage Dream’s “The One That Got Away,” and Zedd throws pretty much everything he’s got at the wall, including an inconspicuous digital clock-tick that screams, “Remember how I coproduced ‘The Middle’?” I’m not mad at it. Undeniably, the best part of the song is that second part of the chorus, with Perry nimbly hopscotching over that steely, almost Robyn-like arpeggiated synth line. We are helpless to resist a fun summer pop song this reliably constructed, for we are all chained to the rhythm.

Much like Miley’s and Taylor’s, Katy’s aim here seems to be course correction after a critically and commercially disappointing left turn. They all seem to be going back to their safe zones: Miley is once again making sad hip-hop-ish songs about drugs (so, so many #drugs); Taylor’s rainbows-and-butterflies album rollout is partially centered around her getting a new cat. (I don’t know what’s more surprising—that one of these artists released a song called “Cattitude” or that it wasn’t Taylor Swift.) Everybody’s partying like it’s 2013. But the way these songs have been received has been a reminder that … it’s very much not anymore? There’s something hermetic about a lot of this music; it feels nostalgic-for-a-few-years-ago in a way that rings false. Remember when Katy Perry played the DNC, what, 39 years ago now?

Harvilla: I refuse to remember that, sorry. Katy’s arc is the most painful: Witness wasn’t terrible, exactly (“I miss you more than I loved you” is a better line than anything on Swift’s Reputation), but her desperation to evolve, to mature, to say something was palpable—and uncomfortable and doomed to failure. “Purposeful pop,” it turns out, is not a thing. As you noted at the time, Miley’s 2017 album Younger Now attempted the same sort of thoughtful rebrand and bricked, so now she’s back to singing stuff like “Wake up in the middle of a breakdown / Have sex on the table with the takeout” and other such calculated lewdness.

I should note that I very much enjoy the last and by far the calmest song on She Is Coming, “The Most,” which is coproduced by Ringer avatar Mark Ronson and achieves a perfect harmony between fluffy and brooding, such that I wish Lady Gaga/Ally had sung it in A Star Is Born. (Miley is apparently releasing three EPs this year, to which I say to you, “Not it.”) But the pop star theme of 2019 seems to be regression: Katy’s back to dance-floor generalities, Miley’s back to cartoon obscenities, and Taylor suddenly sounds younger than she did when she sang about turning “22” seven years ago.

I have tried very hard to make my peace with “ME!,” but the “Hey kids, spelling is fun!” bridge is a slap in the face every single time. Taylor seems to be gunning for a whole new generation of teenagers, but she suddenly sounds way younger and far less worldly/savvy/poised than, say, 17-year-old Billie Eilish. And yet, this past weekend, the long-apolitical Taylor criticized Trump directly in a letter to her senator, Lamar Alexander, declaring her support for the Equality Act. (She also endorsed Tennessee Democrats Phil Bredesen and Jim Cooper in the 2018 midterm elections.)

Her public statements are growing more “purposeful,” in short, as her music gets more childlike. How do you reconcile her increased activism with the giddy regression of “ME!”? Is reconciling that even necessary? Is the key to being a pop star adult to studiously avoid singing like one?

Zoladz: I’ve spent a lot of time thinking about why “ME!” repulses me so, and I think it’s because the chorus sounds like a non-ticklish person trying to convince someone that they know how it feels to be tickled and that is deeply unsettling to me? HEE HEE HEE. HOO HOO HOO HOO OOH! Is this the scientific opposite of ASMR?

Taylor is turning 30 this year, and the sonic-fluffernutter first single off #TS7 does not exactly scream, “I am entering a new decade of maturity.” (Not to bring her new cat up again, but it feels important to note that his name is Benjamin Button.) Swift’s growth has been reflected more in her public image than her music, though, and I agree that it’s a little difficult to reconcile that chasm. I do appreciate how direct she’s been in her political targets, focusing less on empty, headline-baiting jabs at Trump (why feed the trolls?) and more on direct action at the state and local level, which is how most change is made anyway. Hey kids, civic participation is fun!

All of these once-reigning pop stars are suddenly having to contend with new peers, and you’re right to bring internet-bred next-generation upstarts like Billie Eilish and Lil Nas X into the conversation. But we also have to talk about the pop star who’s had the biggest glow-up since these three were last on the scene, Ariana Grande. I see Grande as the middle ground between these two camps: She definitely has the old-fashioned industry backing of someone like Katy or Taylor (thank u, scooter braun), but she’s also rebranded herself quite gracefully as a dominant pop star of the era of the endless scroll. Grande is popular right now because she’s very good at two crucial streaming-generation things: She’s figured out that one big album every three years is no longer a fruitful model of relevance (her more off-the-cuff 2019 release thank u, next came out just six months after her Proper Release Sweetener, and it’s been even more commercially successful.) But she’s also made the boundary between her music and her public persona incredibly porous. “Thank U, Next” was such a smash because of how directly it dealt with what we already knew about her personal life. We’re a long way from Carly Simon’s “You’re So Vain”—Ariana was out here naming names. Even her nod to the “7 Rings” royalties controversy in her one-off single “Monopoly” feels incredibly savvy, proof that she (or at least the people around her) has one eye on the memes. Do you think Katy, Taylor, and Miley could stand to learn something else from their insurgent contemporaries?

Harvilla: Taylor is definitely our reigning champion at Naming Names—“Dear John” remains undefeated—but I agree that Grande has devised a more fluid, nimble, modern, and above all human approach to calling out crap dudes in transcendent pop songs. The #TS7 rollout has only just begun and already feels endless: The pastel Instagram makeover, the endless Easter eggs, her sweaty attempt to glom on to various pop-culture phenomena from Fleabag to Game of Thrones … it all feels so slow, so traditional, so antiquated. And yes, as you say, a 2013 approach counts as antiquated. It’s too perfect that a song as Maximum Internet as “Old Town Road” has already stolen so much of her thunder, to say nothing of everyone else’s.

The problem is that the very thought of Taylor trying to be hip and revolutionary and internet-savvy leaves me exhausted. Moreover, what most people seem to want from her in 2019 is, for her, the ultimate regression: a country album. And a surprise drop of #TS7 would feel like she was ripping off Beyoncé yet again. She’s too big to fail but also too entrenched to innovate; she can’t break the music-industry wheel because she is the wheel. She’s a throwback and a bit of a relic in her very hugeness.

As a near-30-year-old with 10-plus years of fame to her credit, Taylor is also far too young to go the Pink or Kelly Clarkson route and age gracefully into brassy empowerment anthems that all sound like pleasant Ellen episodes unto themselves. But she’s far too old to compete with—or sing like, or convincingly pander to—actual teenagers. (Carly Rae Jepsen, whose new album Dedicated is a very enjoyable slight letdown, is likewise struggling with this what’s-my-age-again dilemma, though she’s already more of a critical enterprise than a commercial one.) Taylor has tons of precedents and tons of disciples, but aspects of her conundrum—how “mature” she can act and how “disruptive” she can really get—still feel unique to her.

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This is all to say that a Katy Perry song called “Teenage Dream” would land quite differently in 2019 than it did in 2010; Miley’s personal and creative arc as a child star turned enfant terrible, in which every new project seems designed to antagonize the fans of her previous project, is even harder to parse. Pop music in the late 2010s is simply moving too fast for even the biggest and best and shrewdest artists to age convincingly, let alone gracefully. They all feel ancient before they even start getting old.

And so, a question: What is the last full-blown pop album that fully connected with you, and felt genuine to where that particular pop star was in her life? (We can pretend male pop stars qualify for this, but from Shawn Mendes to Khalid to the duet-album-bound Ed Sheeran, they all can’t help but feel like diet sodas.) Maybe you already answered this, and verily, I really dug Grande’s thank u, next, too. But is it totally cheating if I say Charly Bliss’s Young Enough? Yes, they’re technically a rock band, and nowhere near popular enough (yet!) to technically be pop stars. But singer Eva Hendricks grapples so authentically with being in her mid-20s while also acknowledging she won’t be in her mid-20s forever, and the hooks are way better, too. Is it just that it’s impossible to make music that vibrant and “real” in too bright a spotlight?

Zoladz: Neverending shout-out to Charly Bliss. I too am nostalgic for that brief moment of possibility when it seemed like #TS7 might be Taylor’s back-to-country album—remember when Diet Prada thought the pastel color scheme meant she was ripping off Kacey Musgraves? Ah, April 2019, were we ever so young? The ultimate irony here is that, while “Old Town Road” continues its benevolent reign, few pop stars in recent memory have had more of a history with the country music than Taylor and Miley. I mean, Miley’s dad has the no. 1 song on the planet right now! You’d almost expect her to exploit that a little more. To quote my favorite stupid-brilliant lyric from her stupid-brilliant 2013 record Bangerz, “Why I need his millis when I got Billy on the speed-dial?” Never been more true!

It’s kind of wild, when you think about it: Both Taylor and Miley ascended to superstar status by consciously shedding their country cred, and now they are struggling to connect with a pop world buzzed on that yee-haw juice. Since they now are, as you aptly put it, “too entrenched to innovate,” they have to settle for playing second fiddle to Miley’s dad and an artist who, this time last year, was best known as a meme-generating Nicki Minaj stan. What’s good indeed?

If this pop-country craze sticks around long enough, though, it might be the best possible scenario for Taylor and Miley (and maybe Katy Perry too, who has never met a set of cultural signifiers she hasn’t felt compelled to try on for size). It’s not exactly evident from She Is Coming (God, that title), but there’s this deep, exquisite sadness to Miley’s voice that she can really unleash on a twangy ballad. If you somehow don’t know by now, her cover of “Jolene” owns. And I still believe that Taylor has never been better than she was on Red, the 2012 blockbuster that found her balance between communal pop impulses and sharp singer-songwriter observations. I fell into a loop the other day of listening to one of her best songs, “All Too Well,” on repeat, just marveling at the craft of it (“so casually cruel in the name of being honest” is an all-time burn) and how good Taylor can be at making hyper-specific feelings (in this case, “breaking up with Jake Gyllenhaal”) feel astonishingly universal. That’s what pop music’s all about, whether it’s wearing a cowboy hat or not. Perhaps it’s not too late for these artists to really correct course and make a hard swerve back to the old town road, from whence they came.