Chappell Roan, the drag-pop star who won’t hurry her second album

Chappell Roan

Photo: Popdust / CC BY 3.0, via Wikimedia Commons

Born	February 19, 1998 Willard
Occupation	Singer
Awards	Grammy Award for Best New Artist

The woman in the red curls and the drag-queen makeup is a character, and her creator has never pretended otherwise. Chappell Roan calls her a drag persona, a louder and braver version of the Missouri girl who wrote the songs, and compares the arrangement to Hannah Montana. The trick worked better than anyone planned. The character now draws the biggest daytime crowds some festivals have ever seen, while the person underneath keeps telling those crowds that the speed of it frightens her. Since the Grammy for Best New Artist she has released two singles and one guest verse, and she has said her second album could be years away. Pop’s newest headliner is running her career at the pace of a person.

The character has a family history. Kayleigh Rose Amstutz grew up the oldest of four children in Willard, a small town outside Springfield, in a conservative Christian household where church came three times a week and summers meant Bible camp. She won her school talent show at thirteen singing The Christmas Song and soon began uploading covers to YouTube. A summer at the Interlochen Center for the Arts produced Die Young, the original song that brought record labels to her door. She was born on February 19, 1998, and by May 2015, at seventeen, she had signed with Atlantic Records.

The stage name arrived in 2016, when her grandfather Dennis K. Chappell died of brain cancer: his surname, plus a word from his favourite song, The Strawberry Roan. The early Atlantic material, the EP School Nights in 2017, was moody and slow, and sung, by her own later account, wrong. The change came after she moved to Los Angeles in 2018, where she says she first felt able to live openly as a queer woman, and began writing with the producer Dan Nigro. Pink Pony Club, released in April 2020, is the hinge: a synth-pop fantasy about a small-town girl who leaves for Los Angeles to dance on a go-go stage. Critics loved it. Atlantic, unimpressed by the sales, dropped her that August.

What followed explains how she behaves now. Roan worked as a production assistant and in a doughnut shop, then, when Nigro’s attention moved to Olivia Rodrigo‘s Sour, at a drive-through back in Missouri. She kept writing. By 2022 she had a Sony publishing deal and was back with Nigro, singing backing vocals for Rodrigo and opening her Sour tour. The independent singles Naked in Manhattan, Femininomenon and Casual sharpened the voice: bratty, funny and queer in plain sight.

In 2023 Nigro set up Amusement Records, a label created specifically for her, with Island Records behind it. Hot to Go! came with its own cheerleading routine. The Rise and Fall of a Midwest Princess, her debut album, arrived in September 2023, and its tours booked drag queens as openers and gave a dollar per ticket to the Black trans support group For the Gworls. The album sold modestly at first. Then, in April 2024, came Good Luck, Babe!, a standalone single about a woman talking herself out of loving another woman, and everything moved at once. The song climbed to number four on the Billboard Hot 100, and the seven-month-old album rose to number two on the Billboard 200. Her Lollapalooza set that August drew the festival’s largest daytime crowd, and Best New Artist followed at the MTV Video Music Awards and, in February 2025, at the Grammys.

The fame came with a problem the industry would rather she kept quiet about. In the summer of 2024 Roan posted that some fans were harassing and stalking her and trying to reach her family, and that liking her music did not entitle anyone to her time. Part of the internet heard ingratitude. Her Grammy speech went further, asking record labels to pay developing artists a living wage and provide health insurance, and drew a public rebuttal in The Hollywood Reporter from the former music executive Jeff Rabhan, who called the idea naive. She answered by challenging him to match a $25,000 donation to struggling artists. The critical reading of Roan as difficult misses what she is arguing: that the system which dropped her in 2020 is the same one now asking her to be endlessly available, and that the drag character is the only part of her built to be public. The fairer criticism concerns output rather than temperament. Two years after the breakthrough, her catalogue still rests on one album, and every new release has been a single.

The singles have been big ones. Pink Pony Club, five years after Atlantic gave up on it, reached number one in the United Kingdom in 2025. The Giver took her into country, a turn she had teased on Saturday Night Live, and The Subway, a breakup ballad she played live for a year before releasing it in July 2025, became her second British number one and earned nominations for Record of the Year and Best Pop Solo Performance at the 2026 Grammys, losing both. The Visions of Damsels and Other Dangerous Things tour, staged on a castle set, closed at Lollapalooza Brasil in São Paulo in March 2026. The same trip brought a brief backlash when the footballer Jorginho accused her security of confronting his wife and stepdaughter at a hotel; Roan apologised, the guard said he was not on her team, and Jorginho withdrew the claim.

Her newest music belongs to someone else’s record. On October 15, 2026, Rodrigo released a remix of Expectations, from her album you seem pretty sad for a girl so in love, with a new second verse sung by Roan, her first guest feature, produced by their shared collaborator Nigro with a game-show parody video hosted by David Byrne. Four years earlier, the same unknown singer had opened one of Rodrigo’s shows; now she trades verses with her as an equal.

Roan lives in Los Angeles. She is a lesbian and has spoken openly about her diagnosis of bipolar II disorder at twenty-two and about depression that worsened with fame. In October 2025 she launched the Midwest Princess Project, a nonprofit for trans youth and LGBTQ+ communities that has raised more than $800,000. Its first anniversary is her next date: the Super Graphic Spectacular, two benefit nights at the Shrine in Los Angeles on October 21 and 22, 2026, with Lola Young, Tinashe, Caroline Polachek and MUNA on the bill and Roan closing both nights. The second album, still known only by the placeholder CR2, has no title, no date and no promise attached. For now the character takes the stage, and the woman who wrote her decides how often.

Tags: singers, pop, Olivia Rodrigo, Dan Nigro, Chappell Roan, Good Luck, Babe!

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