Last updated: November 15, 2024
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. Although not immediately successful, the album is considered a “sleeper hit” with a cult following.
Roan made her public debut at 13, performing “The Christmas Song” at her school’s talent show, where she took home the top prize. 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 and original pieces on occasion 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” in 2014 which she wrote while attending summer camp at the Interlochen Center for the Arts in Michigan, Roan was quickly signed to Atlantic Records.
Roan did admit she missed out many childhood experiences like going to the prom and attending his high school graduation since she already begun her music career.
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. “Roan” came from her grandfather’s favorite song, 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.”
In 2017, Roan released her first single, “Good Hurt” and an EP titled School Nights. She also supported Vance Joy on his Lay on Me tour all while living with her parents in Missouri and only flying to Los Angeles or New York when needed. However, in 2018, Roan made the decision to move to Los Angeles. A move that benefited not only her career but her physical and mental well-being since she was able to live openly as a queer woman. Roan felt “overwhelmed with complete love and acceptance” and managed to write songs as the “real” her.
Roan was dropped by Atlantic Records in 2020 after the release of “Pink Pony Club,” due to her poor-performing releases. Chappell Roan needed to work as a production assistant, barista, and nanny to support herself. 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 recently concluded her 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!” According to her, it was the “gay girl version” of Oasis’ “Champagne Supernova.”
Reviews of the song were positive. Callie Ahlgrim, senior music reporter and resident pop expert of Business Insider called it the “best song of 2023.” Roan included the song in her tours setlist and in Olivia Rodrigo’s Guts World Tour. Capital, Rolling Stone, NME and Pitchfork all included it in their lists of the best songs of 2023. It was also nominated for MTV’s Video Music Awards in 2024 for Push Performance of the Year.
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.”
“Femininomenon” peaked at no. 69 at the Canadian Hot 100 and no. 66 at the US Billboard Hot 100. Music critics described the song as having a “serious earworm of a chorus.”
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.
In an interview with Into, Roan talked about the song’s origin. “I’ve been through some pretty gnarly breakups. I was just sitting in the session and I was like, ‘Ah, it feels so nice that my ex is doing horrible!'” Roan admitted she knows the song is toxic. But, being the unapologetic drag queen that she is, she wrote it like how she was feeling that day. Critics noted the song’s cynicism but still considers it one of the best songs of The Rise and Fall of a Midwest Princess. She said of the music video for the song, “I didn’t want it to be like a beauty shot necessarily. I wanted it to look kind of scary.”
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
💌| @ChappellRoan on good luck babe
".☘︎ ݁˖ The first song of the next chapter is out this Friday April 5th .☘︎ ݁˖ it’s about wishing good luck to someone who is denying fate ✌️ but sure!! "
-via email pic.twitter.com/jaRPgSyhSc
— CRN (Fan Account) (@ChappellRoanNow) April 3, 2024
/photo/2" target="_blank" rel="noopener">denying fate, as they will be thinking about her years later.
The song is Roan’s breakout song and received positive reviews from music critics. “Good Luck, Babe!” was also included in the mid-year rankings of the best songs of 2024. It’s also nominated for three Grammy Awards for Song of the Year, Record of the Year and Best Pop Solo Performance. Aside from its nominations and positive reviews, the song also made LGBTQ pop artists feel more represented.
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.”
Roan described the concept of the music video for “Casual.” “Aquamarine, but like, gay.” It was also inspired by art films, cabaret, and drag performances, that’s why every night during her tour, she invited local drag queens to open for her as a way to pay back the community that inspired her so much.
