Leading up to the Grammy nominations on Nov. 16, Rolling Stone is breaking down 11 different categories. For each, we’re predicting the nominees, as well as who will (and who should) win on Grammy night.
The Grammy Award for Best Pop Solo Performance was introduced 14 years ago, merging Best Female, Male, and Instrumental Pop Vocal Performance into one category. Among its biggest winners are vocal powerhouses Adele and Olivia Rodrigo, though the category is not without its surprises. Lola Young won for her quietly powerful performance of “Messy” in 2026, beating out nominees Lady Gaga and Sabrina Carpenter, while 2025 saw Miley Cyrus’ ubiquitous “Flowers” win the accolade. Best Pop Solo Performance can be a space where the Recording Academy recognizes — and perhaps awards — artists with songs that truly connect with the world, regardless of vocal chops.
Brooke Reese, the host of Apple Music’s Global Chart Show, says that beyond radio play and chart domination, audiences appreciate an evocative and vulnerable performance, which doesn’t always require jaw-dropping vocals. Music fans want pop music that makes them feel something, whether it’s to get up and dance, quietly weep, or scream along. When it comes to this year’s nominees, “People need authenticity,” Reese says. “I think we’re all just craving that.”
Best Pop Vocal Performance – Our Predictions
Olivia Dean, “So Easy (To Fall in Love)”
Olivia Rodrigo, “Drop Dead”
Slayyyter, “Brand New Chanel$”
Sombr, “Homewrecker”
Harry Styles, “American Girls”
Who Will Win?
Olivia Dean, “So Easy (To Fall in Love)”
The British pop singer had a major breakthrough last year after winning Best New Artist, and is already shaping up to be a Grammy favorite. Her sophomore effort The Art of Loving was released last September, after the eligibility period ended for the 2026 ceremony, so all those songs are fair play, including the bossa nova swooner “So Easy (To Fall in Love).” “Olivia Dean is an artist I love and adore, [I] just knew there was something special about her,” Reese says. “The minute that The Art of Loving came out, I felt like there was nothing like it at the time.” Dean’s vocals are syrupy sweet and evocative, fitting the idea of what many would consider a true “performance,” and the track has been everywhere in the year since it was released. Grammy voters will have a hard time not falling in love with Dean’s charm.
Who Should Win?
Olivia Rodrigo, “Drop Dead”
Rodrigo had already been writing Grammy-winning love songs since her debut in 2021; “Driver’s License” won this award in 2022 and she’s poised to take it home again with “Drop Dead.” Rodrigo’s third album You Seem Pretty Sad for a Girl So in Love displayed a marked maturity in her artistry and its lead single, “Drop Dead,” melds her greatest sensibilities into an infectious lovesick ditty. Her voice on the starry-eyed chorus helps check off the capital-P performance criteria, and she gets kudos for letting her inner theater kid come out on the quirky second verse. Her tangible growth, too, should resonate with the Recording Academy (the Livies certainly notice it). “[Rodrigo is] one of those young female artists who knows exactly who she is and exactly the stories she wants to tell,” Reese says. “She’s grown through her last few projects, especially into this one.”
Forecasting the Field
This year’s nominees are a series of battles; Olivia vs. Olivia, America vs. England, the old vs. new guard. Dean and Sombr were among last year’s nominees for Best New Artist, though their recorded work fell outside of the eligibility period, so we may end up seeing pop’s newest voices usurping seats in the category from the genre’s biggest voices (Taylor Swift, Ariana Grande, Bruno Mars, etc.). “We’re gonna see a big wave of [Best New Artists nominees] because they were just on the cusp of huge moments with their music,” Reese says. “I feel like we’ll see more of them at the 2027 Grammy Awards. “
More than ever, Reese says, people are connecting with authenticity. “With social media, there’s nowhere to hide. You can’t not be who you are… The more authenticity we’re getting from artists and their performances, the more people are going to connect with it.” That’s why she believes soft-rock sad boy Sombr may receive a nomination in this category and beyond. “He is one of my favorite artists right now,” she says. “There’s something so brilliant in his vulnerability.” She also recognizes he’s taken naysayers’ opinions as a challenge to improve on his craft. “Instead of letting it break him, he took it and said, ‘Okay, let me prove to you why I’m doing what I do.’”
That’s also why Reese believes electroclash star Slayyyter could nab a nomination. Slayyyter was ready to hang things up as she released her third album Wor$t Girl in America this spring, but the combination of a fiery Coachella performance, TikTok trends, and an album stuffed with good-ass pop music led to one of the year’s most notable breakthroughs, seven years after she dropped her debut mixtape. “Brand New Chanel$” will appear on her companion follow-up to WGIA$, and is one of her most accessible (and best) songs yet. “I feel like this is [Slayyyter’s] time,” Reese declares. “Slayyyter has never changed who she is or the type of music she’s made. In the likes of Charli XCX, she’s never strayed from who she is to fit in.” Reese also notes Slayyyter spent years cultivating her sound and fanbase without once sacrificing her true self. “Everybody finally caught on.”
Where does this leave pop prince Harry Styles, who swept at his last Grammys with Harry’s House? Like so many before him, Styles found transcendence at the techno club on his newest album, Kiss All the Time. Disco, Occasionally, and previously won Best Pop Solo Performance for “Watermelon Sugar.” This combo of dominance and vulnerability means he could take the category once again with “American Girls,” where he struts to the discotheque looking for love (and with tears in his eyes). Either way, the trend report of the 2027 Grammys is this: vulnerability is in.
Daniel D`Amico for SANREMO.FM
