Olivia Dean Predicted to Win 2027 Grammy Pop Solo Award — SkimNews
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- Rolling Stone is breaking down 11 Grammy categories ahead of Nov. 16 nominations, predicting five nominees led by Olivia Dean, Olivia Rodrigo, Slayyyter, Sombr, and Harry Styles for Best Pop Solo Performance.
- Olivia Dean's 'So Easy (To Fall in Love)' is the predicted winner — her sophomore album 'The Art of Loving' was released after the 2026 eligibility cutoff closed, making every track fair game for the first time.
- Olivia Rodrigo's 'Drop Dead,' the lead single from her third album 'You Seem Pretty Sad for a Girl So in Love,' is Rolling Stone's pick for who should win, with Apple Music's Brooke Reese praising her marked artistic maturity.
- Slayyyter is positioned for a potential first nomination with 'Brand New Chanel$' after a breakthrough built on a fiery Coachella set, TikTok momentum, and her third album 'Wor$t Girl in America' — seven years after her debut mixtape.
- Harry Styles' 'American Girls' from his new album 'Kiss All the Time. Disco, Occasionally' keeps him in contention; he previously won this category for 'Watermelon Sugar' and swept with 'Harry's House.'
- Apple Music's Brooke Reese said the category will reward authenticity and vulnerability this year, specifically championing 'soft-rock sad boy' Sombr for 'Homewrecker' and noting that audiences 'can't not be who you are' in the social media era.
- Recent category history backs the vulnerability thesis: 2026 winner Lola Young beat Lady Gaga and Sabrina Carpenter with the quietly powerful 'Messy,' and 2025 went to Miley Cyrus's ubiquitous 'Flowers.'
Why it matters: The predictions frame authenticity and vulnerability as the dominant voting criteria this cycle — a notable shift that could elevate first-time nominees like Slayyyter and Sombr over established Grammy heavyweights. With 2026 winner Lola Young having upset Gaga and Carpenter, and Dean's entire album sitting in this eligibility window, the Nov. 16 nominations will test whether the Recording Academy continues rewarding emotional rawness over vocal spectacle.
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