Chappell Roan performs at Justin Tranter And GLAAD Present "BEYOND" Spirit Day Concert on October 19, 2022 in Los Angeles, California.

2024 is Chappell Roan’s year, from her commanding stage presence to leading the charts. The queer Missouri native, born Kayleigh Rose Amstutz, started her music career with a heavy influence from ’80s synth-pop and early 2000s pop hits. Her debut album, 2023’s The Rise and Fall of a Midwest Princess, is an example of that “campy” sound.

Universal Music Group's 2024 After Party Presented By Coke Studios And Merz Aesthetics' #SmartTox, 5 of Chappell Roan's Best Songs Ranked
(Photo by Jon Kopaloff/Getty Images for Universal Music Group)

At 14, Roan auditioned for America’s Got Talent without success. Reflecting on her audition, she said, “I didn’t make it; I had no idea what I was doing.” Determined to make it in the music industry, she began uploading covers to YouTube under the name Kayleigh Rose, drawing attention from various record labels and fellow Queer icon Troye Sivan. After she uploaded her original song “Die Young,” Roan was quickly signed to Atlantic Records.

Behind the Name

While signed, the musician adopted the stage name Chappell Roan (pronounced “Chap-pel Row-an) in honor of her grandfather, Dennis K. Chappell, who died of brain cancer in 2016. His favorite song was the 1959 Western song “The Strawberry Roan” by Marty Robbins. She has also expressed dislike for her first name, Kayleigh.

She told Vanity Fair that her stage name is a “drag-queen version of me because it’s very larger-than-life. Kind of tacky, not afraid to say really lewd things. The songs are kind of the fairytale version of what happened in real life.”

Roan was dropped from the label in 2020 after the release of “Pink Pony Club” due to her poor-performing releases. A few years later, in 2022, Roan released songs independently before releasing her debut album through Island Records in 2023. The album’s commercial breakthrough was helped by Roan’s supporting act spot on Olivia Rodrigo’s Guts World Tour, her performances at music festivals like Coachella and Governors Ball, and the success of her follow-up single, “Good Luck, Babe!”

In a 2022 interview, Roan said she considers her sound as “slumber party pop.” She recalled attending slumber parties and listening to Lady Gaga and Ke$ha with a friend, who would also cry with her to Adele. “I try to capture that feeling of youth, pure bliss, and exploring sexuality,” she said of her music writing.

Chappell is currently on tour, supporting her album, The Rise and Fall of a Midwest Princess.

Take a Look Below at 5 of Chappell Roan’s Best Songs Ranked:

  • 5. Red Wine Supernova

    Going with an ’80s feel, the second track from The Rise and Fall of a Midwest Princess shows how Roan’s sexual awakening has helped her outlook on life with relief. While wearing her mini skirt and go-go boots, the artist goes through the stages of love as a “Red Wine Supernova” falling into her. She said of the track, “I needed a campy gay girl song that captured the magic of having feelings for another girl. I packed the song with fun raunchy lyrics that make it feel like a night out flirting with the girl across the bar!”

  • 4. Femininomenon

    As the opening track of her 2023 debut studio album, “Femininomenon” explores why a man can’t “hit it like rom-pom-pom-pom.” Chappell said in a previous interview that the track is about the confusion she has about her sexual relationships with men. “Something is not connecting. I feel like every man I’ve been with is never satisfying. With a woman, it’s easy and different and wonderful. It’s a phenomenon. It’s a queer song – hidden in there.” The phenomenon the pop star describes in the song is this “magical, perfect scenario somewhere out there exists, and it’s probably a woman in my case.”

  • 3. My Kink Is Karma

    “My Kink Is Karma” sounds like a Taylor Swift song at the start, from Chappell’s vocals to her lyrics, “We broke up on a Tuesday, kicked me out with the rent paid. Ruined my credit, stole my cute aesthetic.” The singer-songwriter finds it “hot when you have a meltdown” and lists all the bad things she hopes happens to the person who broke her heart. What we love most about the track is that anyone who has been wronged in a relationship can take satisfaction in imagining the worst happening to that person, and this song is a fun way to let that out.

  • 2. Good Luck, Babe!

    This is the song taking over all of the charts and airplay. “Good Luck, Babe!” gives us the energy of a Kate Bush track as Chappell wishes the person who is hiding their relationship the best of luck. She sings, “And I cry, it’s not fair. I just need a little lovin’, I just need a little air.” Throughout the song, she struggles with wanting to call it off and ultimately letting that person be filled with regret and denying fate, as they will be thinking about her years later.

  • Casual

    This synth-pop track dissects Chappell’s friends with benefits relationship in excruciating detail. “I’ve heard so many rumors that I’m just a girl that you bang on your couch.” As a 20-something, Chappell perfectly describes the current dating world of relationships that are usually categorized as “complicated” or friends with benefits. She asks how, if things are casual, then why are things more intimate and why is she meeting family? Trying to navigate as a woman how to hold her tongue and give space, the artist states that she just simply isn’t the “chill girl.”

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