The Rise and Fall of a Midwest Princess is the debut album for Chappell Roan, the alias for Kayleigh Rose Amstutz. I know that this album was released in the fall of 2023 and exploded in popularity in 2024, but I cannot get enough of my new favorite album! The rumors are true and Chappell’s take on pop will be something like you’ve never heard before.
While Chappell has expressed how a midwest princess mindset means embracing your individuality in light of societal expectations, the album explores the highs and lows of Chappell’s personal journey. From discovering her queer identity to leaving her hometown of Willard, Missouri, and eventually moving to Los Angeles.
As a quick explanation for some of the subject matter discussed in the songs, Chappell formerly dated men, but has since come out as a lesbian. Chappell is also an alter ego and outlet for some of the more conservatively-raised Kayleigh’s queer girl fantasies. With that being said, here’s my ranking of the songs on The Rise and Fall of a Midwest Princess.
14. “Guilty Pleasure”
As “Guilty Pleasure” is the closer for the album, it aptly is also the closer for this ranking. It’s strange because Chappell herself has stated that the song is her personal favorite that she wrote, yet I never hear anyone talk about it in any context. It’s not bad, but it’s not my favorite either, and as part of such a stellar and standout album, it has to go at the bottom of my ranking.
With its sporadic key changes and an entire bridge of yodeling, “Guilty Pleasure” no question fits in with the eclectic aesthetic of the rest of the album. In particular, I love the juxtaposing nature and the manner in which she sings the lines, “And oh my god, you are heaven sent/With your dirty mind, yeah, you’re perverted.” While it’s last on this list, I agree with Chappell that having a song named “Guilty Pleasure” perfectly encapsulates the spirit of the album overall.
13. “California”
As a warning, many of the songs ranked lower on this list could be categorized under the “fall” aspect of Chappell’s journey, or less pretentiously known as a ballad. I appreciated “California” because it gives us insight into Chappell’s origins as a professional songwriter and singer. The song depicts how Chappell signed with Atlantic Records at 17, moved to LA, and was subsequently dropped in 2020 after her single “Pink Pony Club” didn’t chart the way the music label wanted it to.
She would then return to Missouri and work various minimum-wage jobs, until signing with producer Dan Nigro’s label, “Amusement Records.” The song discusses the disappointment in yourself and the perceived disappointment from your loved ones after failing to achieve your risky dream. The song is a bit monotone compared to the rest of the album for me. However, as someone who dreams of moving away from her Midwestern hometown, I understand the separation anxiety behind the lyrics of, “Come get me out of California/No leaves are brown/I miss the seasons of Missouri,” on a different level.
12. “Coffee”
Another ballad for the album, “Coffee” explores the thoughts behind desiring to see your ex post-breakup, but simultaneously acknowledging how you probably shouldn’t. In this song, the narrator is someone who still has feelings for her ex and is trying to figure out how to see them again without putting herself in a position to get hurt. She reasons if they get coffee instead of wine, then things will just be fine, but concludes the song that they shouldn’t attempt anything if there’s still something there.
As someone who has tried to reconnect with her ex knowing that her ex definitely does not want to get back together, some could say I relate. I’ve grown to realize though that this behavior can be self-destructive and can only hold you back from a relationship where both people truly desire to be with one another. Chappell doesn’t explicitly reciprocate this sentiment, but you can deduce from your ultimate decision that she is on a path to discovering this, which I love, of course.
11. “My Kink Is Karma”
Now, I know this will be a controversial pick. This song is not a ballad in the slightest, but again it’s a slower song this time with a soft rock twist. I think choosing a genre that you can headbang and belt along with was perfect, since it is a song about that toxic feeling you get when you’re glad you know your ex is doing bad. Trust me, crying out the lyrics, “It’s hot when you have a meltdown/In the front of your house and you’re getting kicked out,” will help heal your soul.
Due to this, I know this song is a favorite among many and I am glad for someone to acknowledge in a song how you know wishing your ex the worst may not be the most emotionally mature, but that doesn’t necessarily mean you’re jealous or that you’re not over the person. Chappell even takes it to the next level by dressing her ex in the music video, Clownie, up as a clown and dominating him after she transforms into her alter ego, Karma. This comes in stark contrast to the reason why Chappell’s personal stage makeup resembles a clown — because of how people in her hometown would call gay people “clowns.” Again, overall I love the lyrical content, but it’s not a song I put on repeat.
10. “Picture You”
“Picture You” has been confirmed by Chappell to directly relate to another song on the album, “Casual,” which we’ll discuss later. The song expands on the idea of being so obsessed with someone who just wants a casual relationship with you. In the song, we see how the narrator constantly ponders about their aforementioned partner, but they’re unsure about if their feelings are reciprocated. As a result, they beg the question multiple times, “do you picture me the way I picture you?”
The lyrical content is quite sad from an outside perspective, but I would say at this point, the narrator has yet to realize that their partner doesn’t want them the same way. Chappell has also stated that she wanted it to have a bit more of a sensual undertone and that definitely reads, not only because of the ensemble of string instruments and piano, but with this context in mind too. For that reason, I think it stands out compared to the other ballads on the album and isn’t as repetitive to listen to multiple times.
9. “Kaleidoscope”
As you can see, I think a lot of Chappell’s song concepts are quite unique and intricate. The types of connections she can make and the euphemisms and metaphors that result are always fun to interpret and analyze. For example, Chappell explained at a concert at the Fillmore that a kaleidoscope is a metaphor for the complexities of queer love. Chappell has fallen in love with a friend, and she cares so deeply for them that she’s fine with remaining as such or exploring their romantic connection.
As she explains, similar to love, if you turn a kaleidoscope, things look different when it’s really all the same. While the character in the song argues that they’re content with staying friends, Chappell wrote them to be a songwriter, which is why they talk about writing songs for their love interest. This was a method to express how dearly they love that person and how much they can do for them, with Chappell’s voice sounding like she’s emotionally in pain. I think the actual song is beautifully complex, to pair with a beautifully complex subject matter.
8. “Femininomenon”
Although I don’t ponder about this topic on the regular, I do not say this lightly — I now have a new favorite word! You could guess the combination of words that form this one, but perhaps not the thought process behind its origins. As someone who has been intimate with both men and women, Chappell can personally testify to her interactions with women being more fulfilling on average. It would be a phenomenon for her to experience the opposite, and it’s feminine.
We’re now at the songs I would argue embody the spirit of the album and its theme to their core. It’s interactive with the gang vocals in the bridge: “Ladies, you know what I mean/And you know what you need/And so does he/But does it happen? (No).” It’s campy with the seemingly random mentions of Papa John’s. It’s upbeat with the magnitude of the song growing as it progresses and prepares the listener for the rest to come. A perfect way to start this album!
7. “After Midnight”
This song is inspired by a saying that Chappell’s dad formerly expressed to her when she was younger: “Nothing good happens after midnight.” Chappell is able to flip her father’s cautionary words and his associated fears with nighttime, in order to create a bubblegum pop song about the types of wonderful adventures Chappell has experienced after midnight, particularly in LA.
The song does refer to kissing both men and women, however Chappell has made it very clear that even the thought of kissing men slightly repulses her. None of the other songs on this album suggest any sort of praise towards her relationships with men, with her deriving this type of fulfillment with women. Instead, these lyrics can be interpreted as Chappell’s desire to stir up a bit of drama with these exhibitionist displays.
6. “Super Graphic Ultra Modern Girl”
The best way I can think to articulate the premise of this song is the auditory conceptualization of “men are from Mars, women are from Venus.” The galactic theme becomes first evident from the vocal echoes and overall composition, and couldn’t be complete without lyrics like, “We’re leaving the planet, and you can’t come.” The intentionality of this decision becomes most obvious once learning how this song is about Chappell feeling out of place when she dated men.
Chappell described in an interview with Capital FM that a super graphic ultra modern girl is someone who is “so confident in themselves and love[s] the fact they’re a freak and weird.” This is most apparent from the beginning monologue where Chappell recalls a date with a man who clearly made no effort in himself or to get to know her as a person. She got the idea for the archetype from an architecture video where the realtor frequently described everything as “super graphic” and “ultra modern.”
5. “Hot To Go!”
“Hot To Go!” is a clear derivative of other instructional dance songs such as, “Cupid Shuffle” or “YMCA,” but that doesn’t inhibit Chappell’s ability to make it her own. Her turn at the genre was created to mimic cheerleader chants because she always wanted to be a cheerleader herself, but as a self-identified outsider, never felt like she could be. Not to mention, hers is about taking a girl home. While Chappell’s grandparents dissociate from her true identity, it’s sweet to see them continue to support her music career and make an appearance in the music video.
Due to its nature, I haven’t seen a song able to get straight men out of their seats and dancing quite like this in a decent while. You can’t help but be uplifted by the upbeat tempo and entranced by the repetitive, but catchy lyrics. Chappell managed to put enough space in between the choruses to make the song fun to listen to every time.
4. “Pink Pony Club”
Now, this or “Good Luck Babe!” was most likely your introduction to Chappell Roan. Some may say it’s overplayed, but its rousing message of self-love and living your truth are universal and never a reason not to sing along. The self-titled Pink Pony Club is inspired by the LA bar, the West Abbey, and Chappell’s admiration of the go-go dancers who perform there. Chappell cites her first time visiting the bar made her want to become a dancer herself.
In “Pink Pony Club,” the narrator’s mother doesn’t approve of her going off to LA to become a go-go dancer, imitating Chappell’s own experience with her mother’s reaction to her sexual orientation and moving to LA to become a singer. While it’s implied through various songs that Chappell’s parents didn’t approve of her sexual orientation, they have stated recently that Chappell has taught them the fruits of respecting people for who they are.
3. “Casual”
While not strictly a ballad, “Casual” is definitely my favorite slower song featured on the album. It begins with slowed, reverberated drums and strings to match the melancholy of beginning a relationship with someone who gives you some of their affection, but never fully in order to remain “casual” with you. However, this is before you realize you’re surviving off the few highlight moments with them, and before you reach the peak of anger after disillusionment — matched by the heightened cacophony of sounds and audible rage in Chappell’s voice at the end.
This song in particular is about a relationship Chappell began during COVID, with a partner who called Chappell their dream girl one week before they texted they were seeing someone else. Chappell would then go on to obsess over what it means to be casual in their eyes as the two would exchange secrets and talk every day. Yes, some of the lyrics and situations are fluffed, but that doesn’t take away from the punch of hearing a very certain phrase for the first time.
2. “Naked in Manhattan”
I would say this song is the most layered with references — all the way from Mean Girls, Lana Del Ray, Astrology, and “Mulholland Drive.” The reference to “Mulholland Drive” in the song is particularly interesting for the way it introduces a deeper exploration or clarification of sexual orientation — as it refers to a scene when two of the main characters, Rita and Betty, have sex. In an intentionally disorienting movie, this moment was meant to be an epiphanic one.
Chappell wrote many of these songs, including this and the next one, before she had even kissed a girl during a confusing time period in her life about her sexual orientation. Her desire to be with a woman however is evident just from the manner in which she writes her lyrics. Her soft outlook on women’s appearances and how the ability to touch them would feel. The mystical vocal layering and feminine production creates the perfect background for the lyrics.
1. “Red Wine Supernova”
My favorite song on this already standout album is definitely “Red Wine Supernova”! The title name is an allusion to an Oasis song entitled, “Champagne Supernova,” yet as one Glamour magazine article highlights, it’s a different kind of wine. A fruitier kind of wine that helps contribute to Chappell’s goal of making this a “lesbian anthem.” Meanwhile, a supernova is meant to depict the intensity of falling for someone.
This could be interpreted as a song about Chappell’s first time being intimate with a woman and learning from an experienced lesbian lover, although Chappell has confirmed she wrote this song before ever kissing a woman. The song overall best embodies the queer kitschiness of the album and everything I love about it. It’s interactive with all the gang vocals chiming in with the “nuh uh girl” bars, and the slowed sections of the chorus keep the composition interesting.
This is a must-listen-to album you guys! I hope to see Chappell Roan continue to gain recognition for the unique quality and genius of her songwriting as she heads down her career path, and especially after her win for “Best New Artist” at the 2025 Grammys.