It takes ten years to become an overnight success. Such is the story of Chappell Roan: your favorite artist's favorite artist.

Roan is the most exciting thing to happen to pop music since Lady Gaga became mainstream in 2009. Whether she's letting out breathtaking belts while running in place or popping out of a giant apple bong dressed as the Statue of Liberty, she's managed to wow some of the biggest crowds in the world. And she's only getting bigger by the minute.

This midwest musicican is actually named Kayleigh Rose Amstutz (her stage name comes from her late grandfather, Dennis Chappell, and his favourite song, "The Strawberry Roan"). She got her start in the industry when she was 17 years old. She uploaded an original song, "Die Young," to YouTube and was signed to Atlantic Records shortly thereafter. In 2017, she released her debut EP, School Nights...but it wasn't a commercial success. Nor did Roan feel like it was an accurate representation of who she really was.

Once she moved to Los Angeles, Roan came into her own. Her 2020 single "Pink Pony Club," a stylistic departure from her early releases, helped Roan's initial rise to prominence. However, she got dropped from Atlantic that same year due to the COVID-19 pandemic. Even worse? Roan's boyfriend of four years broke up with her the same week she got dropped. Roan had to move back home to Missouri and work a variety of odd jobs to support herself.

Despite the nightmare scenario, Roan didn't give up. In 2020, she also met Dan Nigro: the producer behind Olivia Rodrigo's rise to fame. He helped Roan produce "Pink Pony Club," as well as an entire album called The Rise and Fall of a Midwest Princess. Roan began to incorporate more of her queerness into her bops, as well as more drag queen aesthetic. She was eventually selected as the opening act for Rodrigo's Sour Tour and for Fletcher's Girl of My Dreams Tour. Slowly but surely, Roan got her flowers. And in 2024, she's now becoming a household name.

For this Top 10 list of our favorite Chappell Roan songs, we're going to be sticking to Roan's most recent releases. No offense to School Nights, but the fun, synthy, classic Chappell Roan we all know and love has only been present since The Rise and Fall of a Midwest Princess onwards. Ready? Let's count down!

10. "Guilty Pleasure"

This is a fun little closing ditty on The Rise and Fall of a Midwest Princess. Chappell Roan's songs can generally be a little steamy and explicit, and "Guilty Pleasure" is no exception. The song explains that maybe this "pothead" and "perverted" lover isn't the best for Roan, but she's fantasizing the romance anyways. The chorus in this track is top-notch, especially with the bouncy synths and the clever line, "I want this like a cigarette / Can we drag it out and never quit?"

In a YouTube video about the making of Midwest Princess, Roan explained about the song: "It’s my favorite song that I wrote ‘cause it’s so weird and it’s very me, I feel like. Because I think if I wasn’t so set on, 'This is the world this is how it has to be' I think I would make much weirder more experimental music. And not that that song is that experimental but, it’s just...I just like to make things that are, like, you can wrap your head around. And “Guilty Pleasure” is pretty jarring because of, like, there’s a random key change and then that goes into pop and then it’s just kind of crazy and there’s an entire bridge of just yodeling. So it’s very, um...I think was just like, “You know what? This is the stamp on the album, like, this is weird and I love this.” And it is a guilty pleasure, like, that’s what my queerness felt like, it was like a guilty pleasure, and because I was too scared to just actually enjoy it fully, it was just like a secret, kind of."

9. "Super Graphic Ultra Modern Girl"

Just as the title suggests, this banger is gaudy, very detailed, feminine, and oh-so powerful. In fact, Roan actually tried to get "Super Graphic Ultra Modern Girl" featured in Greta Gerwig's Barbie movie. While it didn't make the cut, it still remains a classic on The Rise and Fall of a Midwest Princess.

We love how loud and proud this tune is with its intergalactic hyperpop sounds. On the making of the song, Roan revealed: "I got that whole concept from an Architectural Digest YouTube video so it’s like a little bit, I don’t really know what it means, you know what I mean? It’s for the listener to decide. The way I even thought of it was like this woman was describing the architecture of this house and she was like, “It’s super modern, this part is ultra graphic with all of the colors,” and I was like, “Ding” and I wrote it down and I kept it in my notes for a long time and then I was like, “How do we make this so how do we make this a pop banger?”

While it's not the most commercially-successful track on Roan's latest record, we think "Super Graphic Ultra Modern Girl" will age well with time. Seriously: listening to this tune makes us want to strut down a high-fashion runway with sky-high heels. (And we won't be wearing any fugly jeans!)

8. "Naked in Manhattan"

Not only does Chappell have songs about the West Coast, but also the East Coast. In "Naked in Manhattan," she sings about a girl crush while celebrating the beauty of New York City. It's all about self-discovery, sexuality, and coming-of-age decked out to a sugary, synthy beat.

"Naked in Manhattan" was Roan's 2022 comeback to pop music after being dropped by her former label, Atlantic Records, in 2020. She also wrote the song while she was dating a man and still coming to terms with her attraction to women. She noted to the LA Times in 2023 that this song, among others on The Rise and Fall of a Midwest Princess, were “wish-casting” for her first gay crush:

"I was dating a boy then," Roan said. “I had never even kissed a girl when these songs were written. It was all what I wished my life could be.”

She later told NME, about the inspiration for the song: "I was just yearning and longing for this feeling, and it was so close I could taste it, but I hadn’t experienced it yet...It was very apparent that I was not supposed to be dating this guy,” she continues, “but I was so scared [to go there with a woman] that I wrote a song about it instead.”

7. "Casual"

A stirring rock-tinged ballad about something that plagues modern dating: situationships. The angsty "Casual" is about a muse Roan is hooking up with. To them, their fling is just casual. But to her, it means so much more. The muse is also making their intentions confusing to Roan – especially since their parents have invited her to their house in Long Beach and her favorite bra already lives in their dresser. Roan is losing her mind over this person...but she is also afraid to let them go.

"Casual" is based off a real situationship Roan found herself in. She revealed, "The whole song came from like, I heard from their friend that they were saying it was casual, when I didn’t think it was. I did not think it was, but apparently it was, so. And to me I was like, how could this be? How could this be casual?" She also explained when promoting the song on TikTok, "I wrote this song bc I am legitimately so tired of love turning into situationships. And I know my friends are so tired about hearing about the s--t show of my love life."

Not only is the song super vulnerable and well-crafted, but so is the music video. In it, Roan falls in love with a monstrous siren. They have a fanciful romance...until Roan realizes the siren's only real concern is murdering foolish men in the water.

6. "My Kink Is Karma"

If you're looking for something a little more vengeful and dramatic than Taylor Swift's "Karma," Chappell Roan's "My Kink is Karma" was made for you. In this song, Roan explores the idea of how the universe will eventually bring justice to those who do wrong – in particular, an ex-lover of hers.

On the song, she told Into More, "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!’ Which is insanely toxic. The song is toxic! I’m very aware that it’s not healthy. But that’s how I was feeling that day."

Despite the toxicity, "My Kink Is Karma" is a very cathartic listen. It comes halfway through the tracklist on The Rise and Fall of a Midwest Princess, and feels like a nice cooldown after the two upbeat songs it follows. And let's not forget the stellar music video, which includes Roan humiliating her clown ex while wearing a sultry devil costume, and a sneaky reference to Dolly Parton's "Jolene."

5. "Pink Pony Club"

This pretty ballad was written right after Roan visited West Hollywood’s iconic gay bar The Abbey, which features male and female go-go dancers and regular drag shows. She released "Pink Pony Club" in 2020, but was unable to perform it for about two years due to the COVID-19 pandemic halting concerts.

Story-wise, "Pink Pony Club" is told from the perspective of a Tennessee girl leaving her hometown for Santa Monica, and becoming a dancer at the fictional Pink Pony Club (which may, coincidentally, not be so fictional considering fans have discovered a gentlemen's club in Atlanta with the same name). The song also addresses the terrified reaction her conservative mother would have upon realizing her daughter has become a go-go dancer.

If anything, "Pink Pony Club" is meant to serve as an anthem for West Hollywood, which has a high population of LGBTQ+ residents. More specifically, it's an ode to the freedom queer people are able to experience within the magic of a gay bar.

4. "HOT TO GO!"

This is one of three Chappell Roan songs to chart on the Billboard Hot 100 due to commercial success. "HOT TO GO!" has peaked at #35 on the chart, and it's no surprise why: it's full of camp, cheerleader pep, and it even comes with its own dance!

In a press statement shared, Chappell Roan said of the upbeat track: "I wrote this song so I could live out my cheerleader fantasy! I just wanted to make something simple and silly that I could do with the audience because I'm a huge fan of audience participation. Also, selfishly (and shamelessly) wanted to bounce around on stage singing a song about being hot."

The music video was directed by Jackie Zhou and was filmed in Chappell Roan's hometown of Willard, Missouri. It features appearances from Chappell's grandparents and drag queens, and shows our sapphic pop princess dressed in an array of show-stopping outfits.

We really do believe "HOT TO GO!" has now become our generation's "Y.M.C.A." Which is fitting, considering both of those tracks can been be interpreted as gay anthems!

3. "Red Wine Supernova"

Sure, you've heard of the Oasis song "Champagne Supernova"...but have you heard of Chappell Roan's "Red Wine Supernova"? Like "HOT TO GO!", this track has also received some commercial acclaim from music lovers, peaking at #46 on the Billboard Hot 100. It's about Roan falling head-over-heels with a girl she's just met. On the song's creation, she said, "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!"

Indeed the lyrics are raunchy on this one, but they're also insanely clever and cheeky. Fans particularly love the double entendre, "I heard you like magic / I've got a wand and a rabbit!" (Yes, that's an allusion to both stage magician work and, well...sex toys.)

Ultimately, "Red Wine Supernova" is nothing short of fun and frisky.
It's also a perfect song for the summer. We also really love the music video on this one, which sees Roan falling in love with a magician girl and turning the local magic-phobe into a cute bunny.

2. "Femininomenon"

You may or may not be surprised to see this track so high on our list. In any case, we believe "Femininomenon" is a slightly underrated song in Roan's discography. It's also the opener – and was meant to be the original title of – The Rise and Fall of a Midwest Princess, so that explains why it's so dang good.

Like "HOT TO GO!", "Femininomenon" tends to be a crowd pleaser at Chappell Roan shows. Of course, “Femininomenon” is a combination of the words “feminine” and “phenomenon.” Chappell created the word with her co-writer, Dan Nigro, because it was “a phenomenon if sleeping with a man was better than sleeping with a girl.”

There's a lot to adore on "Femininomenon" - from the intricate music production (love the motorcycle sounds added in for spice), the mix of ballad and pop rock bop, the call and response aspects ("but does it happen? NO!"), and Chappell's hilarious delivery of "Did you hear me? PLAY THE F---ING BEAT!!!" This song will most definitely leave you energized, and perhaps craving a "Femininomenon" of your own.

1. "Good Luck, Babe!"

This song has possibly become something of Roan's magnum opus. "Good Luck, Babe!" is not part of the song lineup on The Rise and Fall of a Midwest Princess. It was actually released in April 2024. But due to its catchiness, poignant story, dramatics, and because it has one of the best bridges ever created in pop music...it's become a bonafide hit for Roan.

On “Good Luck, Babe!”, Roan looks back on a secret relationship with a woman from her past, and the struggle with her lover's compulsory heterosexuality that broke them up. You can hear the sadness, rage, and pride when Chappell belts that iconic chorus, "You can kiss a hundred boys in bars / Shoot another shot, try to stop the feeling / You can say it's just the way you are / Make a new excuse, another stupid reason." Roan's sarcastic tone also implies that her ex will fail in trying to hide her feelings for women. In a strange way, "Good Luck, Babe!" is a sort of pride anthem for queer folk, because the message of the track is that you can't deny your feelings for someone, no matter who it is.

This passionate song only took Roan three short minutes to write, but it's gained countless commercial success. It originally debuted at #77 on the Billboard Hot 100 chart, but then climbed to #10 during the week ending July 13, 2024. Roan has had several standout live performances of the track, including the San Diego concert premiere of the song, her breakout Coachella set, and her incredible late-night act on The Tonight Show Starring Jimmy Fallon. During that performance in particular, she received a standing ovation from the studio audience. We can't wait to see what future song will give her a standing ovation next!

Check out our selection of free stations streaming Chappell Roan music at Live365.com.

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_{Article Image: While crouched, Chappell Roan belts into a microphone and points during a concert. (Jason Martin [CC BY-SA 2.0] via Wikimedia Commons)}