9 Songs From Pop’s ‘Middle Class’ That Deserve to Be Hits

Dear listeners,

On Monday, The Times published a piece by the critic Shaad D’Souza that asked a question I’ve been pondering a lot over the past decade: “What happens when a pop star isn’t that popular?”

D’Souza created a taxonomy of a relatively varied assortment of musicians — among them Carly Rae Jepsen, Charli XCX, Kim Petras, Troye Sivan and Rita Ora — who embrace pop musical sounds and command devoted, internet-savvy fan bases but still operate below the visibility of “major” pop stars like Taylor Swift and Beyoncé. “For these artists,” D’Souza writes, “pop stardom isn’t a commercial category, but a sound, an aesthetic and an attitude.”

“Pop,” though, is of course short for “popular,” and some purists might dismiss D’Souza’s question as a futile thought experiment: If a tree in a forest releases a single that fails to crack the Hot 100, does it even make a sound? And with detractors quick to label any perceived misstep as evidence that a pop star has entered her flop era, success and failure can now feel like an irreversible binary.

But there are plenty of gray areas, too, and I appreciate the optimism of D’Souza’s conclusion: Hey, it’s a living. “It may be miles away from the spectacle and flash usually associated with pop music,” he writes of this broad career trajectory, “but it does provide a path toward something that, for decades, has proved elusive for a lot of aspirant pop stars: career sustainability.”

The article made me think of something I mentioned in last Friday’s newsletter: Jepsen’s recent sets at Rockwood Music Hall (save it, please!), a tiny venue into which she crammed 150 fans at a time after her outdoor concert at the larger Pier 17 was cut short because of weather. Jepsen seemed to be having a ball leading direct-to-fan singalongs with her frenzied devotees, who may not fill Swift-sized arenas, but who nevertheless adore her. With Eras Tour tickets either impossible to come by or prohibitively expensive anyway, maybe pledging allegiance to a pop star with a more modestly sized fan base is, these days, the more sustainable way to stan.

Though D’Souza makes the argument that the majority of these performers operate in a relatively safe pop playground, adjusted commercial ambitions also free up many of these artists to stop chasing fickle chart trends and make bolder, stranger and more sonically adventurous pop music. I want to celebrate that freedom on today’s playlist, which culls some of my favorite songs from a few of the artists D’Souza affectionately called “pop’s middle class.”

My personal favorites of these are-they-actually-pop stars are generally the more outré ones: the eternal club kid Charli XCX, the vocally dexterous former Chairlift frontwoman Caroline Polachek and the genre-omnivorous British-Japanese musician Rina Sawayama. But, as you’ll hear, I appreciate a solid Jepsen banger as much as the next Jepfriend.

Listen along on Spotify as you read.

1. Carly Rae Jepsen: “Surrender My Heart”

One of my favorite songs from Jepsen’s 2022 album, “The Loneliest Time,” “Surrender My Heart” — a surging synth-pop tune about how difficult it can be to open up to the possibility of new love — has one of Jepsen’s signature anthemic choruses and even some of her wry humor: “I paid to toughen up in therapy/She said to me, ‘soften up.’” (Listen on YouTube)

2. Troye Sivan, “Rush”

The lusty, effervescent “Rush” is the first single from the Australian musician Sivan’s upcoming album “Something to Give Each Other.” Sivan was one of the few cast members not to embarrass himself on HBO’s recent narratively challenged series “The Idol”; it remains to be seen if that increased visibility will push him closer to pop’s A-list. (Listen on YouTube)

3. Caroline Polachek: “Welcome to My Island”

Maybe one of my favorite pop choruses in years? Every time I hear it, I want to shout it off the top of the mountain like the guy from that Ricola commercial: “DESIIIIIIIIIIRE! I want to turn into you!” That lyric from “Welcome to My Island” also gives Polachek’s latest album — easily one of my most-played of 2023 — its charmingly ridiculous title. (Listen on YouTube)

4. Charli XCX: “Constant Repeat”

“I’m cute and I’m rude with kind of rare attitude,” Charli XCX sings, summing up her own unruly musical personality on this highlight from her sleek 2022 album “Crash,” which lets a flighty would-be lover know exactly what they missed out on. (Listen on YouTube)

5. Ava Max: “Million Dollar Baby”

At her best, Ava Max sounds like Lady Gaga would if she were still making “Fame Monster” B-sides in 2023. I mean this as a compliment; in my opinion, most pop songs should sound like they could have been included on “The Fame Monster.” Ava Max’s biggest hit, “Sweet but Psycho” from 2019, certainly fits this description, but I’m also a fan of this driving 2022 single, which cleverly employs an interpolation of LeAnn Rimes’s 2000 “Coyote Ugly” smash “Can’t Fight the Moonlight.” (Listen on YouTube)

6. Troye Sivan, “Rager Teenager!”

This wistful track, from the 2020 EP “In a Dream,” shows off the softer, sparser side of Sivan’s dreamy pop. It also would have worked as an entry on last month’s exclamatory playlist! (Listen on YouTube)

7. Rina Sawayama: “Bad Friend”

Man, I love this one. File it under “incredibly common life experiences that no one really writes pop songs about”; Sawayama’s wrenching “Bad Friend” chronicles, to the tune of a beautifully melancholy melody, the gradual erosion of a once-close friendship. “So don’t ask me where I’ve been, been avoiding everything,” Sawayama sings, before finding solace in a chorus of people confessing that they can relate: “Put your hands up if you’re not good at this stuff.” (Listen on YouTube)

8. Carly Rae Jepsen: “Cut to the Feeling”

Jepsen — bless her — has an unfortunate tendency to bury some of her best work, and it’s possible that has hampered her ability to achieve another pop radio smash. Consider that the single she released after “Call Me Maybe” was a painfully twee duet with the guy from Owl City (if you don’t remember Owl City, I’m jealous of your brain), or that she kicked off her “Emotion” era by releasing as a leadoff single that excellent album’s very worst song, “I Really Like You.” (At least she got Tom Hanks in the video.) “Cut to the Feeling,” from 2015, is an absolutely perfect, ecstatic, 10-out-of-10 pop song, and if you have never heard of it before that’s because it was released on the soundtrack of a Canadian-French animated film called “Ballerina.” At least you get to hear it now! (Listen on YouTube)

9. Charli XCX: “Track 10”

Many of Charli’s Angels — this one included — consider the gleefully forward-thinking 2017 mixtape “Pop 2” to be Charli’s magnum opus (so far) and this epic finale to be one of her most successful experiments. D’Souza highlights Charli as a musician who has straddled the worlds of mainstream pop and its more risk-taking underground, and a clear distillation of that contrast can be heard in the two different versions she’d recorded of one particular song. “Blame It on Your Love,” from her 2019 album “Charli,” is a glossy, radio-friendly tropical house jam, complete with a by-the-numbers guest verse from Lizzo. “Track 10,” though, is something else: A wildly weird deconstruction of a pop song, culminating in an escalating bridge that sounds like it’s being sung by a malfunctioning laser printer. Some songs are so special that something would be lost by even giving them a title. So this one, fittingly, is just “Track 10.” (Listen on YouTube)

Desiiiiiiiiiiire,

Lindsay

The Amplifier Playlist

Listen on Spotify. We update this playlist with each new newsletter.

“The Best of Pop’s ‘Middle Class’” track list
Track 1: Carly Rae Jepsen, “Surrender My Heart”
Track 2: Troye Sivan, “Rush”
Track 3: Caroline Polachek, “Welcome to My Island”
Track 4: Charli XCX, “Constant Repeat”
Track 5: Ava Max, “Million Dollar Baby”
Track 6: Troye Sivan, “Rager Teenager!”
Track 7: Rina Sawayama, “Bad Friend”
Track 8: Carly Rae Jepsen, “Cut to the Feeling”
Track 9: Charli XCX, “Track 10”