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Sabrina Carpenter Writes Her Next Chapter: ‘I Feel a New Sense of Freedom’

A couple of years ago, Sabrina Carpenter would tell people that she wanted to experience heartbreak. It was in jest, mostly — but also it wasn’t. As a young singer-songwriter, Carpenter desired the artistic clarity of emotional pain.

“To my friends, I was always like, ‘I just want to know what Adele’s feeling,’” Carpenter tells Billboard in between bites of ravioli during a breezy early-fall afternoon in lower Manhattan. “Like, how she made these gut-wrenching records. And I [just became] so fascinated with that… like, ‘Damn, I just need some of whatever Adele was drinking!’”

She pauses. “And… then I got it.” Carpenter takes a hard swallow and adopts a careful-what-you-wish-for grimace, the lightness of her conversation dropping away for a few seconds before quickly coming back. “It was super-eye-opening, and I am grateful for it all,” she recovers. “But it’s still tricky to navigate.”

At 22, Carpenter has already experienced more of life than most artists her age, as a particularly prolific dual-threat former child star. The Lehigh Valley, Penn. native had finalized a label deal with Disney Music Group’s Hollywood Records at the age of 14 as a home for her family-friendly pop; in the same year, she signed on to co-star in the Disney Channel series Girl Meets World, a job that lasted over 70 episodes.

Her warm on-camera presence drew the attention of young viewers, while her breathy, agreeable songs drew millions of streams and cracked Billboard’s Pop Songs chart on four occasions. Before hitting the legal drinking age, Carpenter had already appeared in over a dozen movies and TV shows, and released four full albums. When the volume of that work is brought up, Carpenter exhales slowly, sets down her mocha latte, and nods.

The gap between Carpenter’s 2019 album Singular: Act II and her in-the-works next album is already the longest of her career, and even if the upcoming project (release date TBD) hadn’t been informed by a breakup, Carpenter believes it would have still been markedly different than her previous output. For one, she has new collaborators — Julia Michaels and JP Saxe, the “If The World Was Ending” duet stars and real-life couple that Carpenter says have worked on “more than half the record” with her. That record will also be her first on her new label home of Island Records, which finalized a deal with Carpenter in January, and was created primarily in New York City, where she’s stayed most of 2021 after spending years on the opposite coast.

Last month, Carpenter released a single, “Skinny Dipping,” that’s decidedly not from a teenage perspective — not because it’s as tawdry as its title suggests, but because it focuses on an awkward coffee-shop encounter with an ex that’s relatable for any twentysomething living in a big city. (The title refers to a desire for transparency and closure with that ex, to “take it all off and just exist / And skinny dip in water under the bridge.”) Carpenter’s point of view as a songwriter has changed, as it was always going to. “No one is going to make the same record at 13 as they do at 20,” she points out.

Written by Carpenter with Michaels, Saxe and producer-songwriter Leroy “Big Taste” Clampitt, “Skinny Dipping” is marked by detailed verses that recall Michaels’ own oeuvre at its conversational best, as well as a technically impressive vocal take from Carpenter, who oscillates between play-by-play speak-singing about the run-in and dipping her voice toward a yearning croon. The song sounds practically nothing like the Sabrina Carpenter of Radio Disney fame, but also, a natural fit for her as a singer and storyteller, as she lays down track for an adult music career.

“Something I’ve always loved and aspired to do is not compare myself to other people, but compare myself to myself,” Carpenter explains, “and just try to consistently grow in a way that feels honest. And you know, that’s tricky when you’re a young girl, and you have a lot of factors weighing into it, and a lot of cooks in the kitchen. And so this last year, not only did I go through so much in my personal life, but the people around me that have grown up with me — my team, my family, my friends — they also I think were ready to just watch me go off and do my thing.”

So have her fans, says Carpenter, many of whom are still young and supporting the former Disney star through a transitional year as a songwriter. Before “Skinny Dipping,” Carpenter released “Skin,” a barbed single that was widely perceived to address a rumored love triangle (more on that later). She also released a video snippet labeled “Intro,” that may preview a song titled “Emails,” in which Carpenter sits down at a piano and delivers a series of wrenching lines full of damaged love and cynicism. If emotional pain has indeed helped Carpenter find her voice this year, she’s reveling in the way it’s upended expectations for where she’s heading.

“I do feel a new sense of freedom,” asserts Carpenter. “I think the fans just don’t know what to expect — which is kind of what I’ve always loved about making music.”

Carpenter has always seen herself as a musician first, even as Girl Meets World — a Boy Meets World spinoff in which she played Maya, the self-assured best friend of series lead Riley (Rowan Blanchard) — was enjoying its run on the Disney Channel, and prominent roles in films like The Hate U Give and Tall Girl kept coming. “Music is the only career that is fully, 100 percent me,” says Carpenter, who was posting covers on YouTube as a 10-year-old — songs by Lady Gaga and Christina Aguilera, but also Ozzy Osbourne and Sinead O’Connor.

When Carpenter released her debut single on Hollywood Records, “Can’t Blame a Girl /for Trying,” she was 14, a natural performer still feeling her way through the beginnings of a career. Her Hollywood output skewed toward general-audience pop-rock with smatterings of bubblegum and balladry, with more mature gestures on later songs like “Looking at Me” and “Exhale” — and a stage show heavy on live instrumentation, with covers of songs by Arctic Monkeys and Twenty One Pilots tossed in to demonstrate a wider range than her albums carried.

Looking back on her four full-lengths with the label — which have earned a combined 745,000 equivalent album units, according to MRC Data — Carpenter believes that her gradual desire for more input was a natural symptom of her artistic development at the end of her teens. “Creatively, I was still able to grow, because I think people did see that transition still even when I was with [Hollywood],” she says. “As I would get older, I was just more comfortable in my own skin and my own ideas.” Yet that confidence would lead to frustrations about the direction of her album campaigns, according to Carpenter: “The amount of times that I really believed in a song? Those weren’t the songs that had music videos.”

Ultimately, Carpenter, who describes herself as “somewhat of a private person,” believes that entering the world of songwriting sessions as a teen was always going to be a difficult process. “A lot of the time, you’re getting introduced to these songwriters, and it’s like speed dating,” she recalls. “I was meeting someone, and then having to tell them all about my life in 30 minutes, and then writing a song, in one day. It felt so impersonal, and I never felt like I was telling the truth.”

The beginning of Carpenter’s relationship with Island was also impersonal, out of necessity: at the height of the pandemic, she was forced to meet with new labels over Zoom. Carpenter had already been writing songs at the beginning of quarantine, and played the Island brass a few things she had been working on; their excited response, and vision for where those songs fit into Carpenter’s adult narrative, helped finalize a deal.

The label’s collaborative nature has been key during a transitional time for Island as well, with president/CEO Darcus Beese departing one month after Carpenter announced her deal, and new co-CEOs Imran Majid and Justin Eshak set to begin on Jan. 1, 2022. “I obviously joined Island at a very interesting time!” Carpenter says with a wide smile. “[But] I think they see this record in the same way I see it, and I’m so grateful for that.”

Carpenter has also found kindred spirits in Michaels and Saxe, who joined her in New York over the summer to work through the bulk of her Island debut. After years of rapid-fire writing brainstorms, Carpenter felt like she has actual peers in her process for the first time — friends who have become close collaborators, and who don’t require a lengthy backstory to understand what she’s going through. Carpenter has dropped cheeky comments in Michaels and Saxe’s gooey Instagram photos together, and created a “crying playlist” of just their songs when she needs to conjure some tears on a film set (“I sent it to them with a picture of me sobbing, and was just like, ‘Thanks, guys!’” she says with a laugh).

Most importantly for Carpenter, the songwriting pair are fellow perfectionists, not bothered by long hours tinkering with a song or a quick decision to trash something that isn’t working. “Bet U Wanna,” a sultry, slow-burning new track that splits the difference between rhythmic pop and psych-rock, resulted from Carpenter hearing a bass line that she liked at 3:00 AM in the studio and proceeding to hammer away from there. The reason the vocals on the chorus are so soft, she says, is because she was falling asleep with the mic in her hand.

As relaxed and disarming as she is in person, Carpenter’s artistic drive is off the charts. “From selectively choosing her songwriter and producer collaborators, to weighing in on mix passes, it’s been incredible to work alongside an artist who gets completely immersed in every creative step along the way,” says Island A&R Jackie Winkler.

For the team at Island, who have developed young stars like Shawn Mendes and Demi Lovato into arena-conquering adult performers, Carpenter’s hands-on approach has been a pleasant surprise at the start of their working relationship. “It’s really what has made all the difference in making the most authentic and personal music to her possible,” Winkler continues. “It’s like the fans are getting the music hand-delivered by Sabrina.”

Carpenter says that her next album will sound different from “Skin,” the synth-led ballad that she issued last January as her first official release on Island. She never intended to release the song as a lead-up to her fifth full-length — in fact, she wasn’t sure if it would ever be released. “That was a song which, unfortunately, was what I was going through, at a time in my life where I couldn’t ignore it,” Carpenter says. “When I wrote the song, I don’t know if I anticipated it being heard — which is probably why it came from a much more truthful place.”

Upon its release, “Skin” was perceived as a response to Olivia Rodrigo’s smash hit “Drivers License” and the rumored love triangle between Rodrigo, her High School Musical co-star Joshua Bassett and Carpenter. After Rodrigo sang that her ex was “probably with that blonde girl, who always made me doubt/ She’s so much older than me/ She’s everything I’m insecure about” on “Drivers License,” “Skin,” released two weeks later, included lyrics like “Maybe then we could pretend/ There’s no gravity in the words we write/ Maybe you didn’t mean it/ Maybe blonde was the only rhyme.”

Thanks in part to the intrigue, “Skin” became the first Hot 100 hit of Carpenter’s career, debuting at No. 48 and earning 60.4 million on-demand U.S. streams to date. Months after its release, she says the experience was “overwhelming,” partially because of how she thinks the song was misperceived.

“So yeah, the Internet has definitely f–ked some s–t up,” Carpenter says before breaking into a laugh. She’s still not interested in clarifying the intent of “Skin” or naming names — as she puts it, there’s nothing more pointless than explaining a song line by line.

“It’s such a waste of time, because you’ll never know the truth,” Carpenter continues. “That’s part of the fun of it, I guess. But at the same time, there are real people. I will say, that’s the hardest thing — trying to be truthful to yourself, make art that feels real and exciting, but then also knowing that [you’re writing] about humans going through what we’re all going through on a daily basis.”

intro pic.twitter.com/p1d2HZ0D9X

— Sabrina Carpenter (@SabrinaAnnLynn) August 7, 2021

That balancing act, between writing with emotional honesty and protecting personal details, is “essentially what inspired the record,” says Carpenter, even if “Skin” may not be on it. She threads that needle on the “Intro” snippet, which is seething with outrage and betrayal in a way that Carpenter’s longtime listeners have never heard before; the clip has 1.7 million views on Instagram, and many of the comments are fans begging her to release the full song.

Carpenter isn’t sure how that song, or any of the others from her upcoming next album, will fare commercially — but that’s not her main concern. She feels like she now has the right team and collaborators around her, and wants the world to be as ready for the next phase of her career as she is.

“I just hope that I feel confident and comfortable in what I’m making,” Carpenter says simply, “and that it finds whoever it needs to.”

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