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If you needed further confirmation of Sabrina Carpenter‘s star status in 2024, this week’s Billboard Hot 100 (dated June 29) offers pretty incontrovertible evidence: She occupies two of the Hot 100’s top five spots this week by her lonesome, while also claiming the chart’s apex for the first time.

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“Please Please Please,” Carpenter’s latest single — which debuted behind only Post Malone and Morgan Wallen’s “I Had Some Help” at No. 2 on the Hot 100 last week — climbs that final spot to No. 1 this week. Meanwhile, its predecessor “Espresso” is still lingering around the top five, sliding from No. 3 to No. 4. Both songs are expected to be on Carpenter’s upcoming Short n’ Sweet LP, now one of the most-anticipated pop albums of the year.

What does it mean for Carpenter that “Please Please Please” became her first No. 1? And what can other pop aspirants learn from her phenomenal 2024 success? Billboard staffers discuss these questions and more below.

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1. This week, Sabrina Carpenter scores her first Hot 100 No. 1 with “Please Please Please,” while its predecessor “Espresso” remains in the top five on the chart. Does this feel like a particularly notable coronation moment to you for Sabrina, or is her stardom already practically old news at this point?

Christopher Claxton: I think this is a particularly notable moment for Sabrina. She’s already a star, we know that, but it’s pretty surprising that none of her tracks have reached No. 1 on the Hot 100 until now. In all honesty, I expected “Feather” to get to No. 1 or at least the top 5. “Feather” did go No. 1 on Billboard‘s Pop Airplay chart, but it’s different when you have a No. 1 on the multimeric Billboard Hot 100. Ultimately, I think she’s finally getting the airtime her tracks deserve.

Lyndsey Havens: The thing that I’m loving about Sabrina’s success right now is that there has been a sustained string of notable coronation moments over the past few months – and all the while, she’s not only managing to repeatedly top herself but also ensure no bit becomes too stale. It was just this March that “Feather” was Sabrina’s biggest hit to date, and that followed “Nonsense,” which felt like that would be her biggest hit. Then came “Espresso,” and it felt like that would surely be her biggest hit, and now here we are with “Please.” To me, this kind of momentum is increasingly rare – and entirely deserved. But now that “Please” has indeed become her biggest song to date, scoring Sabrina her first Hot 100 No. 1, I’m curious to see what could happen next. Where do you go when you’re already at the top?

Jason Lipshutz: “Espresso” opened the floodgates for Sabrina Carpenter as an A-list pop artist, but one could have argued that she was still a one-smash wonder, as she scored her first top 20 hit with an undeniable refrain. The ascent of “Please Please Please” erases any doubt that Carpenter is among pop’s upper tier, though — especially considering that it climbed higher than “Espresso,” with both a less immediate hook and more subtle approach. Carpenter was already a star prior to “Please Please Please,” but her first Hot 100 chart-topper ensures that her stardom will transcend her breakthrough hit. 

Andrew Unterberger: The Coachella and Governor’s Ball gigs she played after the respective releases of “Espresso” and “Please Please Please” felt like the coronation moments to me. But this is kind of an “If you don’t know, now you know” moment for Carpenter’s burgeoning A-list status: In case the memes and live clips and streaming totals didn’t persuade you, there’s really just no arguing with having two of the top five songs (including the No. 1) on the Hot 100 during one of the most competitive moments in recent pop history. She’s a superstar.

Christine Werthman: Let’s go straight to the source, shall we? “MY FIRST #1 on the @billboard HOT 100!!!!!!! And espresso at #4,” Carpenter wrote on Instagram. “I’m very immensely grateful so i will surely always remember this day for the rest of my life!” Others might consider her a star already, but the No. 1 is the ultimate feather (also a great song) in her cap. This is absolutely a big moment for her. 

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2. While “Espresso” put Carpenter at top 40’s forefront and generated a ton of Song of the Summer buzz, “Please Please Please” has already reached commercial heights in two weeks that “Espresso” has yet to reach in over two months. What is it about “Please” that allowed it to become her first song to get over the top on the Hot 100?

Christopher Claxton: Several factors contribute to the rapid success of Sabrina Carpenter’s “Please Please Please” compared to “Espresso.” For one, it’s catchy and relatable, thus able to resonate more with a broader audience. Carpenter also has a new group of fans after she finished supporting Taylor Swift on the Eras Tour. Her fanbase is not only more active in streaming and promoting her music due to the consistent success of her previous songs, but she also has a new set of supporters, contributing to the greater anticipation built around the song.

Additionally, Sabrina co-wrote “Please Please Please” with Jack Antonoff, who has worked on every Swift album since 2014. Bringing Taylor Swift supporters to her fanbase, along with a song written in a style that those fans enjoy, is a pretty reliable recipe for success. The sound and timing of the twangy pop song is another important factor: From Beyoncé’s “Cowboy Carter” to Shaboozey’s “A Bar Song,” country music has been at popular music’s forefront lately.

Lyndsey Havens: Momentum. “Espresso” was like this perfect delectable appetizer that fed fans while also increasing the appetite for more – and “Please” is the whole meal. I do think part of its success needs to be credited to Jack Antonoff, who has such a way in the studio of creating addicting, fiendish melodies that beg repeating – like the glittering opening synths that arrive with a bit of unexpected twang and the little swish and hand claps that occur in between the first and second parts of the chorus. But even more so than the production elements that shine is Sabrina’s delivery, especially on a viral one-liner like, “I beg you, don’t embarrass me motherf–ker.” 

Jason Lipshutz: A combination of three things: newfound interest in Carpenter’s music post-“Espresso,” which has elevated her all the way to arena headliner level already; the pedigree of “Please Please Please,” complete with Jack Antonoff and Amy Allen studio credits and a flashy music video co-starring Carpenter’s romantic partner, Barry Keoghan; and the quality of the song itself, which hoists up Carpenter’s wry sense of humor and whisper-pop bluntness within a shimmery production that flirts with country balladry. It’s a singular song that arrived at the right time, and was presented in a compelling way.

Andrew Unterberger: “Momentum” about sums it up. “Please Please Please” is a fundamentally weird song, shifting keys and modes and tones and even genres throughout its three minutes — it’s fun and it’s compelling and it’s cool but if it wasn’t released by Sabrina Carpenter at this particular moment in time it seems unlikely to me that it would’ve been a big hit. But because Carpenter has pushed all the right buttons for years now and built her audience the right way, they’re more than willing to follow her down some windier paths now. And so a twisty country-pop hybrid like “Please Please Please” can outchart even a no-doubt smash like “Espresso,”” because her fans trusted that it would be worth sticking with, and were rewarded with a song that was sneakily even more addictive than its predecessor.

Christine Werthman: The comedic, bad-boy video with her real-life boyfriend, Barry Keoghan, garnered plenty of attention and has over 36 million views (“Espresso” has accrued nearly twice that many since its April release), but “Please Please Please” has a lot more going for it than just the visual. While “Espresso” was, fittingly, a spunky shot with a TikTok-able lyric (“I’m working late/’Cause I’m a singerrrr”), “Please,” though only a few seconds longer, makes it feel like Carpenter is taking her time.

The Jack Antonoff production adds a dreamier vibe than her other songs, marrying watery synthesizer and electric guitar with tender acoustic guitar and some irresistible background claps. Where “Espresso” maintains the same energy and tempo throughout, “Please” builds with a subtle key change and a sparkly outro, as well as a narrative that gives it that extra tension. While both play to Carpenter’s humorous strengths, “Please” is a more dynamic song overall.  

3. When you think of this breakout period of Carpenter’s a decade from now, which of the two songs do you think will come to mind first?

Christopher Claxton: For me, I think it’ll be “Espresso.” It’s my favorite out of the two, and a song that I think can be played no matter the mood you’re in, since it’s feel-good music — whereas in “Please Please Please,” she’s begging a man not to break her heart, which is less all-purpose.

Lyndsey Havens: “Espresso.” Though “Please” has emerged as the bigger hit, you never forget your first, as they say. Plus, the “I’m working late, ’cause I’m a singer,” line has permeated into popular culture — and clever quips like that can often stick around well beyond the lifespan of the song itself.

Jason Lipshutz: “Espresso” still — I love “Please Please Please,” but Carpenter’s emergence came from a summer-defining powerhouse, full of bubbly personality and quotable lyrics. Maybe “Please Please Please” will stand strong at No. 1 for multiple weeks as “Espresso” slips down the chart, but I think it’s more likely that “Espresso” hangs around the top 10 for multiple extra months, and becomes one of the biggest hits of 2024, even if it never musters its way up to the chart’s very peak. And when we look back at this time many years from now, we’ll be thinking about “that’s that me espresso” and “I’m working late/ ‘cuz I’m a singerrrrr.”

Andrew Unterberger: For all her many great songs already — and likely many more to come — “Espresso” will always be the one that put her on that higher pop plane. It’s not a perfect comparison, but I think of the two songs as somewhat analogous to Ariana Grande’s “Thank U, Next” and “7 Rings” duo; the latter ended up the bigger chart hit, but the former was the enduring moment.

Christine Werthman: I will forever be entertained by the line “Heartbreak is one thing, my ego’s another/I beg you don’t embarrass me, motherf–ker.” Flawless. Also, as I have said to some of my colleagues, that triplet “embarrass” makes it even more interesting and sometimes hard to sing! I vote “Please.” 

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4. As someone who’s made practically every right move to build her status from pop fan favorite to unequivocal superstar over the past two years, is there one particular move or strategy of Carpenter’s that you think other artists and their teams can learn from?

Christopher Claxton: One notable strategy that has contributed to Sabrina Carpenter’s rise to stardom is her consistent and authentic engagement with fans on social media. She uses platforms like Instagram, TikTok, and Twitter, actively sharing behind-the-scenes content, personal stories, and interacting with fans through Q&A sessions. This approach has helped her build a strong, loyal fanbase that feels personally connected to her journey. Other artists can learn from this by prioritizing genuine interactions with their audience to foster increased support and loyalty.

Lyndsey Havens: Persistence – and kindness. Over the years, the two things that I think stand out most about Sabrina as an artist and businesswoman is that she has remained incredibly driven and incredibly humble. She’s had so many nearly-there moments tracing back to her start with Disney to signing with Island to entering into the public discourse for one thing or another, but all the while she kept her head down and kept working. That, to me, is the most admirable and applicable thing of all. 

Jason Lipshutz: Over the course of multiple albums, a label switch, singles that didn’t take off and tours that kept getting bigger, Carpenter kept betting on her eccentricities — the quirks that made her songs, style and stage presence unique, from the self-deprecating lyrical passages on Emails I Can’t Send to her tongue-in-cheek merch to the personalized “Nonsense” outros on tour. Carpenter built a fan base by being herself, and that base was ready to stream and support once she landed on a single, “Espresso,” that was primed for a true mainstream moment. If I were an aspiring artist watching Carpenter’s ascent, I would study the way she amplified what makes her special, unflaggingly, over multiple years and projects.

Andrew Unterberger: Never underestimate the value of a good running bit — especially when you’re really winning to commit to it. The evolving “Nonsense” outros were immeasurably helpful in establishing Carpenter as a pop star worth paying attention to, because they were always good and clever and gave you a reason to keep an eye on any major gig she was playing. Her poking fun of her own miniature size (down to the title of her upcoming album) is another good one, one that makes her relatable and human without actually being too embarrassing or explicitly unglamorous. The songs are the most important thing, of course, but a little reliable and identifiable personality always goes a long way.

Christine Werthman: Take your time. Carpenter released four albums between 2015 and 2019, and then took three years before dropping emails i can’t send in 2022. The jump between Singular: Act II and emails is significant, and it shows that she and her team were willing to let her take the time to establish her cheeky style and playful pop sound.  

5. Make one bold prediction about Carpenter’s upcoming album Short n’ Sweet. (It can be about its commercial performance, a special guest/collaborator, a song subject/theme/sound, anything.)

Christopher Claxton: Based on the way she’s growing as an artist and her popularity in streams, I think at least one more of her songs from ‘Short n’ Sweet’ will be in the top 10. I also think we’ll get a lot more songs that are sonically similar to “Please Please Please.”

Lyndsey Havens: At this point, this is practically a decaf prediction, but the album will debut at No. 1 – and stay put there for a bit. 

Jason Lipshutz: Based on “My ‘give a f–ks’ are on vacation” and “I beg you, don’t embarrass me, motherf–ker,” I guarantee that we are in for some SPECTACULAR swearing!

Andrew Unterberger: She works with Max Martin for the first time on one of the singles, and it surprises absolutely no one by zooming right to No. 1 on the Hot 100.

Christine Werthman: Taylor will pop in. Maybe.