On Saturday Night Live’s May 18 season finale, Sabrina Carpenter appeared in a sketch as Daphne from Scooby-Doo, watching in horror as Jake Gyllenhaal’s Fred tore the face off James Austin Johnson’s villain. (The gag: Apple Face ID — Never Get Ripped Off Again!) The sketch was a prelude to Carpenter’s two theatrical performances as musical guest. First, she sang her then-new single, “Espresso,” which had debuted the month prior before her main-stage Coachella set and had already soared into the top 10 of the Billboard Hot 100 and Global 200; then a medley of her first two Pop Airplay top 10 singles, “Feather” (No. 1) and “Nonsense” (No. 10), both released in the preceding year-and-a-half.

Two days later, Justin Eshak and Imran Majid — the co-CEOs of her label, Island Records — gathered their staff at Island’s Manhattan headquarters to rewatch the episode. “She’s just a pro; it was an incredible moment,” Majid says later that afternoon of the 25-year-old singer, who first tasted fame as a Disney Channel actress in her early teens. “For a lot of artists, the idea of translating their performance to television is hard,” Eshak adds. “But because she has so much experience with it, it just felt so much more natural and comfortable for her.”

At the time, the buzz from Carpenter’s SNL debut, coupled with the instant global success of “Espresso,” felt like a mountaintop. After the initial success of “Nonsense,” which reached No. 56 on the Hot 100 in February, “Feather” hit No. 21 and topped Pop Airplay in April. Then “Espresso” exploded, reaching No. 3 on the Hot 100 in June and spending two weeks at No. 1 on the Global 200.

But Carpenter’s momentum has only picked up since. In late June, “Please Please Please” debuted at No. 2 on the Global 200, simultaneously giving her the top two songs in the world. (She maintained that feat the following week, when “Espresso” and “Please Please Please” flipped spots atop the chart.) It also bowed at No. 2 on the Hot 100, making her the first soloist — and second act overall, joining The Beatles — to have her first two top three Hot 100 hits concurrently reach that territory with no other billed acts. The next week, it hit No. 1 on the Hot 100, Global 200 and Global Excl. U.S. charts.

It was the kind of setup that executives dream of: one song building on the next to keep scaling new heights. “We always felt ‘Please Please Please’ had this level of sophistication that really sets her up in a different lens; there’s a bit of Dolly Parton in that song,” Majid says. “But it feels like everything we hoped and dreamed the one-two punch would be.” Or, as Island vp of A&R Jackie Winkler puts it, “ ‘Nonsense’ walked so ‘Feather’ could jog, then ‘Espresso’ ran so that ‘Please Please Please’ could start a stampede.”

That stampede has set the stage perfectly for the Aug. 23 release of Carpenter’s album Short N’ Sweet and the launch of her North American arena tour in the fall, which sold out in every market within two weeks of its late-June announcement. But already, her success has been one of the biggest artist stories of the year so far, and a big feather in the caps of Eshak, 44, and Majid, 42, who took over the esteemed 65-year-old Island in January 2022 after jointly running the A&R department at Columbia Records for three years.

Carpenter is just one example of how the duo has revitalized Island. In mid-June, following her massive performance at New York’s Governors Ball festival, Chappell Roan’s September 2023 album, The Rise and Fall of a Midwest Princess, reached the top 10 of the Billboard 200 in its 12th week on the chart — just the second time this decade that an album broke into the region for the second time after that long of a climb. And in the first week of July, Roan’s single “Good Luck, Babe!” — which became her first Hot 100 hit when it debuted on the chart in April and is not on Midwest Princess — hit No. 10 on the Hot 100 after its own 13-week climb.

Call it the summer of Island. While the likes of Carpenter, Roan, The Killers, Brittany Howard and Remi Wolf are dominating festival stages, their songs are setting new personal high-water marks on the charts. The buzz started building earlier this year: Howard’s first album for Island, What Now, arrived in February to critical praise; that same month, the biopic Bob Marley: One Love, about Island’s most famous artist and featuring James Norton as label founder Chris Blackwell, grossed over $179 million, according to Box Office Mojo. (Island was not involved in the making of the film but did release an album “inspired by” the movie alongside Tuff Gong Records, which featured artists like Kacey Musgraves, Wizkid and Leon Bridges covering Marley classics.) The Last Dinner Party, originally signed by Island U.K.’s Louis Bloom, released its debut album, Prelude to Ecstasy, and was named “Britain’s hottest new band” by The New York Times Magazine in March; in April, Hulu released a well-received documentary on Bon Jovi — which has spent its entire 40-year career as part of Island — before the band’s latest album, Forever, debuted at No. 5 on the Billboard 200 in June; and alt-pop powerhouse Wolf released her heralded sophomore album, Big Ideas, on July 12. The year ahead also promises new music from Carpenter and Roan, while Shawn Mendes, one of the label’s few reliable hit-makers over the past decade, is in the studio.

“Nowadays, everything’s about culture, and company culture, and the philosophy of how you’re doing things, and Island is definitely a label that’s wired differently,” says Nick Bobetsky, who manages Roan. “They’re not the ambulance chasers, they’re not the TikTok-moment chasers. They’re really committed to supporting their artists in a way that’s really true to those artists, and that is rare in today’s climate.”

For Eshak and Majid, it’s validation of the culture that they’ve sought to build since taking over the Universal Music Group (UMG) subsidiary in 2022 — and a testament to the work they’ve done overhauling a label that had slipped down the pecking order as the marketplace evolved in recent years. While the Island Records they inherited — home to Marley, U2, Traffic, Grace Jones and Cat Stevens, among others through the years — may have been rich in history, its more recent track record had been spotty at best, disjointed at worst. Island finished 2021 with a current market share of 0.67%, a number that had fallen steadily over the previous five years, from 1.5% in 2018, according to Luminate.

“We weren’t walking in here inheriting hits. We had to rebuild a roster, which sounds easy but takes time, and no one really knew what the label proposition was,” Majid says. “So we had to go out there and project what that is at a very competitive time.”

But Island’s small roster and small staff allowed it to focus on developing talents like Carpenter and Roan — and to provide that raison d’être that the label had seemingly been missing. That has often meant leveraging the live side of each artist’s career to help catapult new records: The popularity of Carpenter’s “Nonsense,” for instance, was built through the fan response to the city-specific outros she added to each of her opening performances on Taylor Swift’s The Eras Tour, while “Espresso” and “Please” were launched in tandem with her Coachella and Governors Ball performances. “It’s really difficult to break through as an artist anymore unless you have a holistic artist proposition,” Eshak explains.

The label built its strategy for Roan, too, on her live aesthetic; Eshak and Majid tell the story of seeing her perform for the first time at New York’s Bowery Ballroom and how the energy of the crowd struck them more than any of the metrics they had seen on socials or streaming. “The enthusiasm that existed in the crowd was just insane,” Eshak continues. “I remember thinking, ‘How do we tell the story about what happened in Bowery Ballroom to the rest of the world? Because if we can do that, then she’s going to break.’ ”

The small-but-mighty ethos is a cue Eshak and Majid took from Blackwell, whom they visited at his Goldeneye resort on Jamaica’s north coast shortly after starting at Island. “When we took this job, we had such a reverence for Island and its history,” Eshak says. “Hearing Chris Blackwell talk about artists that historically worked on Island, they would weave their way through culture. The artists that are having success now are fan-driven, have unique artist propositions, and you just [have to] support them in the right way. This label has always stood for creativity and for artistry and for things that may not seem obvious but weave their way through culture.”

In some ways, no label is as beholden to, or in the thrall of, its founder as Island. Since being spun back off as a stand-alone label from the combined Island Def Jam in 2014, successive heads of the company have invoked Blackwell, who left in the late 1990s, when articulating their philosophies. “I wanted to go back to the idea of Chris Blackwell-era Island: an artist-driven label that was a major, but in an intimate manner,” then-president David Massey told Billboard in 2016 about his ­approach. In 2019, his successor, Darcus Beese, told Billboard, “How I run my business is literally how I think Chris would run his business.”

Eshak and Majid are similar, often invoking the spirits of Blackwell and the label itself — though with their own spin. “It’s not a throwback company by any means; it’s very progressive and market-focused,” Majid says. “But it’s also about curation. If we’re going to have success in this market and with a new generation of artists, you want artists that feel like they love being a part of the company, and you want people that want to work here. And that was kind of what Chris built at Island Records.”

“I’m so happy that Justin and Imran have continued to honor the heart and culture of the label,” Blackwell, 87, tells Billboard. “Looking back, I remember the rush of excitement when I discovered an act, signed them and saw their massive success. Well done, guys.”

Eshak’s and Majid’s careers have often run parallel over the past 18 years. Both started at Universal Republic under Monte and Avery Lipman in the mid-2000s, when the company had just 23 employees and a small roster; Eshak then spent time at Mick Management before the two reunited in 2013 in Columbia’s A&R department, where they rose to co-heads of A&R. While they seem a study in contrasts — Majid, a New Jersey native, is more outgoing and gregarious; Eshak, from Houston, is more reserved and measured — they’re united by a shared passion and sense of purpose for their artists and their staff, the business and the music, as well as an awareness of their own complementary strengths.

Through their industry arcs, Eshak and Majid have seen the business from Republic’s then-scrappy-upstart vantage point, as well as through the legacy lens of Columbia, one of the oldest and most decorated labels in history. The current iteration of Island, with its immense, venerated catalog and relatively small staff, is something of a combination of the two. “The team at Island is our extended family,” says Janelle Lopez Genzink, Carpenter’s manager. “Every member of the team’s laser focus on delivering in each of their areas has helped us experience these monumental wins.”

But the progress toward this point has not been linear. The duo first needed to overhaul Island, even amid a broader restructuring by UMG. The first two years of Eshak and Majid’s tenure didn’t include much improvement in market share as they reshaped the roster, while UMG shifted Island into Republic Recording Company in early 2024, alongside Republic Records, Def Jam and Mercury, providing resources through its Corps team, with the Island chiefs now reporting to Monte Lipman. Yet despite the reshuffle — and maybe partially because of it and the groundwork laid in those early years — Island has more than doubled its current market share, from 0.62% at the end of 2023 to 1.3% through the end of June.

“Both Imran and Justin are top graduates of ‘Republic University’ from back in the day and have always exemplified the passion, drive and ambition to become leaders in this business,” Republic Recording Company founder and chairman Monte Lipman tells Billboard. “Avery and I couldn’t be more proud of their success in creating such an amazing culture for both artists and executives at Island Records.”

Island’s artists appreciate that culture, too. Carpenter calls Eshak and Majid “collaborative and supportive partners” who “encourage an open dialogue, which is important to me.” “It’s very rare that the higher-ups trust the artist fully,” Roan adds. “It proves Justin and Imran’s method that trusting in the artist results in success and longevity — even outside of music.” And Jon Bon Jovi, whom Majid calls “our Bruce Springsteen,” says the two “truly care about their artists and are supportive and passionate in achieving a shared vision.”

“Certain things are always true: great artists, great artistry, great songs, artists with clear vision,” Eshak says. “But on the business side, it’s almost the opposite, where we’re in a business of constant change. You have to be willing to reinvent yourself and reteach yourself things all the time in this business. And I think, ultimately, the labels that are successful have that approach: They understand culture, they understand what actually moves the needle in the marketplace, and they’re constantly evolving.”

Island’s latest evolution is still developing, with several more emerging artists in the pipeline, Grammy hopes on the horizon and a new partnership with Virgin Music to sign regional Mexican star Carín León — the label’s first true foray into Latin music, which was announced in late June. But for the moment, Majid says, there’s a chance to simply take a breath, look around and appreciate how far they’ve come. “It’s two-and-a-half years of going seven days a week to just catch a break,” he says. “To have a moment like this that we don’t take for granted and we’re very sober about — it’s very fulfilling.”

This story will appear in the July 20, 2024, issue of Billboard.