Chappell Roan is about to hit cities on a pop-up tour, but before she graces a stage near you, it’s time to talk about a key component of her super-stardom: the art of drag. In an excerpt from a new Chappell Roan book out October 7, Chappell Roan: The Rise of a Midwest Princess, writer J’na Jefferson dissects the ways in which drag has influenced Chappell’s stage persona.
But first! Here is more about the book:
Chappell Roan broke through as a superstar, thanks to a genuinely new blend of powerhouse vocals, queer pride and drag queen style. Her appeal is clear: the songs are bouncy anthems that are unabashedly joyful, and her campy looks are a perfect mix of burlesque star and beauty queen.. This stunning gift book immerses you in Chappell’s world, examining her rise to fame, how she established herself so seemingly quickly, and how she is challenging expectations while honoring gay women’s impact on pop culture.
To pre-order the book, click on the retailer or your choice:
AMAZON BARNES & NOBLE BOOKS-A-MILLION BOOKSHOP HUDSON BOOKSELLERS POWELL’S
“Work It Girl” by J’na Jefferson in Chappell Roan: The Rise of a Midwest Princess
Drag as an art form goes way back—dating to the dawn of theater in Ancient Greece. However, the growing visibility of drag over recent decades—in film, on screen, and on stage—has given today’s queer artists, including Doechii and Troye Sivan, more freedom to weave its influence into their music. Chappell Roan, who describes herself as a “singer/songwriter/performer/drag queen,” occupies a unique space as both a wildly successful pop star and a purveyor of drag’s spirit. Her music, aesthetic, and outspoken nature are deeply drag-infused, as she uses her platform to entertain, inspire, and amplify marginalized voices. Her elevation of this once-underground culture into mainstream pop is also reshaping the queer direction of 21st-century pop music.
Chappell Roan: The Rise of a Midwest Princess
“I’ve always noticed when someone is using drag as a prop versus drag as a castmate,” Hanukah Lewinsky, a drag performer in New York City, explains of Chappell’s appreciation for the drag community, which has been proudly reciprocated. “There have been artists [in the past] who have had drag queens on stage, and [the queens] haven’t been paid, they don’t get tagged, they don’t get any recognition.”
“When Chappell has drag queens with her,” Lewinsky adds, “it’s ‘this is so-and-so, this is where you can find their art, this is where you can find what they do.’ We’re her co-stars.”
Lewinsky is among the performers who replaced Chappell at the 2024 All Things Go Music Festival after Chappell pulled out of her set for health reasons. The last-minute set, dubbed “Queens of the Dancefloor” by festival coordinators, was curated by NYC-based drag star Beaujangless the night before the event, and included several drag performers, such as legendary queen Kevin Aviance, festive background dancers, and DJ B-Roc of The Knocks.
“Drag queens are used to getting something ready that’s very exciting, very quickly,” Lewinsky said. The queens stood in for the singer, lip-syncing and dancing to a slew of Chappell songs for about 45 minutes. “The crowd really loved it—in that moment and online. The general consensus felt like we were able to add something exciting and new to that day,” explains Lewinsky.
“It was by far the coolest experience of my life thus far. Just that I got to do it to music that I love, for an artist that I love, with such close friends, it was 10/10. I wouldn’t change it for the world,” Lewinsky says.
THE IMPACT OF DRAG
Though Chappell’s music reflects her queerness and affinity for drag, drag’s influence on the music industry is hardly new. In the 1930s, “Pansy” performer Jean Malin recorded songs referencing queer identity; while in the ’50s, rock pioneer (and former drag queen) Little Richard’s flamboyant stage persona paved the way for future LGBTQ+ performers. David Bowie’s experimental sound, costumes, and theatrics were key in pivoting pop in a queer direction. Elton John’s “lifelong love affair” with drag and a friendship with Divine encouraged the Rocket Man’s over-the-top costumes. In the 2010s, rapper Nicki Minaj embraced drag elements, notably with her alter ego “Roman Zolanski,” which toyed with gender norms. Chappell is continuing a tradition set in motion long before her reign.
“Pop and rock specifically have always been informed by queer culture, and drag is also part of that conversation,” explains Elyssa Maxx Goodman, the author of Glitter and Concrete: A Cultural History of Drag in New York City. “[Chappell’s rise] has the possibility of continuing drag’s presence in mainstream culture.”
NBC//Getty Images
CHAPPELL’S USE OF DRAG
Chappell’s discography is a proclamation of her queer identity, using drag-inspired themes to amplify self-discovery, empowerment, and resistance. “Pink Pony Club” celebrates queerness while exploring somberness, creating a drag-evoking emotional juxtaposition. “Femininomenon” flips the script, proudly embracing queer sexuality. She blends pop with elements of country, alt-rock, and folk (at times in the same song) mirroring how drag fuses high art with low culture. This art form has long challenged boundaries, not only of gender but also of music, bringing power to Chappell’s work.
Pop has used drag to create visual spectacles rooted in queer resistance and celebration. Through bold, avant-garde makeup and costumes—like her signature white face paint, a nod to her hometown’s homophobes who called queer kids “clowns”—Chappell is helping normalize drag’s aesthetics. “The people in my hometown would call gay people ‘clowns.’ That’s why I actually wear white face [drag makeup], because of how those people called us clowns. I was like, ‘Bitch I’ll show you a clown,’” she said to an audience in Manchester.
Steve Jennings//Getty Images
Goodman notes that Chappell highlights femme drag, a style in which women or nonbinary people dress in drag, popularized by performers like Fauxnique and Crimson Kitty. Chappell’s drag-heavy aesthetic in her music videos and live performances adds to her allure. In the “My Kink Is Karma” video, she plays a lingerie-clad devil/clown, a nod to the apparently queer character HIM from The Powerpuff Girls. She also frequently uses blue eyeshadow, a deliberate tribute to the sex workers and drag queens who have been unfairly demonized. As Chappell put it in Faces of Music, a documentary series sponsored by Sephora: “Blue eyeshadow is so stigmatized…and it’s all connected to why I picked it.”
“Drag and drag aesthetics have long been part of how pop musicians visually connect to their audiences,” Goodman says, referencing Cher’s Bob Mackie costumes, Madonna’s Marie Antoinette–inspired outfit at the 1990 MTV VMAs, and Lady Gaga’s early career looks, including her 2011 drag king persona “Jo Calderone.”
Chappell’s stage presence is bold and playful, drawing from drag’s performative theatrics where every move tells a story. This allows her to explore both lighthearted and darker themes, reflecting drag’s ability to blend cheek and earnestness. And she uses her live performances to advocate for LGBTQ+ rights and visibility. At the 2024 Governors Ball music festival, Chappell called for “freedom for all oppressed people” while dressed as the Statue of Liberty. A week later, at the Kentuckiana Pride celebration, she performed in full drag, paying tribute to legendary queen Divine and her iconic role in the 1972 film Pink Flamingos.
STANDING UP FOR DRAG
“I feel like any time [Chappell has] a big platform, she lets people know that drag is here to stay,” New York City queen Mo’Riah says about Chappell’s commitment to drag. Like Lewinsky, Mo’Riah was one of the performers asked to dance in Chappell’s place at All Things Go, a moment she says made her “feel like Beyoncé,” adding that Chappell “always stands up for [drag queens.]”
“[Chappell’s] touchstone comes at a time where there’s a very odd turn back to ‘We don’t want anything that’s out of line,’” Lewinsky notes of the tepid climate Chappell is finding her success in, where queer and trans rights hang in the balance and are even under direct attack. “It would be so easy for someone to fit into what society deems appropriate, but it’s nice to have someone who says, ‘Fuck that, we’re not going to tailor ourselves for what you deem is right or acceptable.’ It’s very energizing.”
Bruce Glikas//Getty Images
Lewinsky, who uses she/her pronouns while in drag, also performed during the New York stop of Chappell’s Midwest Princess Tour. Chappell supported local drag acts by having them open for her during these shows, sharing the spotlight with performers who’ve been an integral part of her artistic journey.
“The first time I ever saw Chappell is when she came to one of my weekly gigs at Pieces,” the popular West Village gay bar, Mo’Riah adds. “She even stayed after and watched the other show after ours. It’s clear she loves drag, and she loves the community and the art of it, I think that’s beautiful.”
Unlike artists who may incorporate drag aesthetics without nourishing deeper ties to the community, Chappell’s integration feels genuine. She’s part of a wave of queer artists who aren’t just referencing drag—they’re making it a core part of their artistic DNA. Her drag persona is theatrical, but it’s also authentic.
“[Drag] just feels like freedom,” Chappell says in Sephora’s Faces of Music. “It lights up something in my brain, it’s just pure serotonin.”
— By J’na Jefferson, Chappell Roan: The Rise of a Midwest Princess
Chappell Roan: The Rise of a Midwest Princess by Jennifer Keishin Armstrong, Dibs Baer, Patrick Crowley, Izzy Grinspan, J’na Jefferson, Ilana Kaplan, and Samantha Olson will be released by Hearst Home Books on October 7, 2025. To preorder the book, click on the retailer of your choice:
AMAZON BARNES & NOBLE BOOKS-A-MILLION BOOKSHOP HUDSON BOOKSELLERS POWELL’S
Disclosure: Hearst Magazines is the parent company of Hearst Home Books and Cosmopolitan.
Related Story