Chappell Roanhas been having a moment lately, you could say. Actually, there’s been a hype train surrounding her (or doing continuous laps around her?) for about a year now, maybe longer, so it would be more accurate to say she’s been having many moments lately. That doesn’t make sense. But neither does Chappell Roan, in a good way. She’s enigmatic as a figure, yet eerily good at making approachable and mass-appeal popmusic.
But, to continue on with how much of an outlier she is, that music still has some kind of edge to it, sometimes lyrically, even while the melodies are simultaneously so catchy and immediate. She has a devoted fanbase after only one full studio album, 2023’sThe Rise and Fall of a Midwest Princess, and yet she’s also been provocative and willing to say things that challenge certain people, andsometimes even the industry at large. And even though she only has one album, a couple of non-album singles, and a 2017 EP (that will be completely ignored here), shealready has enough memorable songs to make a ranking of the best ones worthwhile, and that’s what the following intends to do. Who knows what she’ll do next, but it will probably be great, or weird, or poppy, or unexpected, or alarming, or somehow all of the above.
10"Super Graphic Ultra Modern Girl"
Released: August 13, 2025
So, there aren’t many Chappell Roan songs. She’s beenworking to get onto the scene for years, but her time on the scene is still relatively recent, as of 2025. That aforementioned debut album was released in 2023, and her popularity grew rapidly throughout 2024 (that was probably her year, more so than 2023). Anyway, all that necessitates the selection of some “deep cuts” if you want to rank Roan’s best songs and include 10 or more, so here’s “Super Graphic Ultra Modern Girl.”
Yeah, being placed here, it’s like, the ninth-best song on an album that has 14 songs, butThe Rise and Fall of a Midwest Princessis such a great album, that still counts for something.This one’s fun, energetic, and feels like a rather successful – and intentionally kitschy – mishmash of somegenres and styles popular in the 1980s. It’s got attitude, and it’s a good song that’s potentially overshadowed by some of the other (even better) songs on the album it belongs to.
9"Naked in Manhattan"
Released: June 13, 2025
In the same boat as “Super Graphic Ultra Modern Girl” is “Naked in Manhattan,” which might qualify for “deep cut” status even more than that aforementioned song, given this song is the third-last on the album. 14 tracks is quite a lot for a pop album, but “Naked in Manhattan,” as track #12, is strong enough pop to keep the energy going at this later stage. And it is pretty well-paced as an album, with the second half not being far off the first half quality-wise.
Anyway, “Naked in Manhattan” is most memorable for its hook, which has Roan singing “Touch me” more often than the phrase is probably said inThe Rocky Horror Picture Show.Given Roan’s drag queen–influenced aesthetic, it might well be a reference to the movie (the song’s shout-out toMean Girlsis more explicit). In the end, “touch me” issaid 39 times in just three and a half minutes, which works out to one “touch me” every 5.4 seconds, on average. Maybe that’s too many. But the song still works, dammit.
8"Guilty Pleasure"
“Guilty Pleasure” is too great to qualify assomething that’s actually a guilty pleasure. Instead, it’s more accurate to call this arguably the most underrated song onThe Rise and Fall of a Midwest Princess. It’s the final track, so maybe people are just overwhelmed by all the catchiness and aggressively strong hooks found in the previous 46 minutes' worth of music to properly appreciate this one, but those same people would be missing out.
The second half of the album is a bit more mellow. Honestly, if there is a flaw with the album, it might be that “Picture You” and “Kaleidoscope” are placed together, at tracks #9 and #10, respectively. They’re slower songs back-to-back, and the album has better slow-ish songs than those.But at least the album concludes with a carefree, breezy, anthemic banger. “Guilty Pleasure” isn’t one you’ll feel guilty about liking, but it does feel intentionally silly, to some extent, though Chappell Roan sells it, as per usual. Sorry for sounding like a broken record already. The commentary’s only going to get more broken as the songs get even better.
Released: August 03, 2025
So, after casting slight shade at “Picture You” and “Kaleidoscope” (not bad songs; just a bit underwhelming compared to the gold they’re surrounded by), here’s some praise for a great slower song onThe Rise and Fall of a Midwest Princess. The first three songs on the album are pretty high-energy, then “Coffee” is a jarring comedown.But what follows “Coffee” is “Casual,” and this has more punch as far as ballads go.
Chappell Roan foregrounds her sexuality and vulnerability throughout most of her best songs, and that side of her music comes out extra explicitly in “Casual.” It is kind of abouthook-up culture and casual dating, particularly within LGBTQ spaces, but it handles the subject well and will feel relatable if you’ve ever found yourself struggling to stay afloat in the world of online dating, regardless of your sexual orientation. The song is explicitly about lesbian romance, sure, but the sentiment and heartbreak of it all can be appreciated no matter what you identify as. And that’s one of the reasons why Chappell Roan has found breakout success, and isn’t just niche. You feel the emotion here, no matter what, and that a song with such unapologetically graphic lyrics can also be so moving is a clear sign of phenomenal songwriting.
6"Femininomenon"
Released: June 16, 2025
Yes, perhaps the silliest song onThe Rise and Fall of a Midwest Princessis also the fifth best. Or maybe it’s even better if you favor Roan’s bouncier songs over her slower ones. Whatever the case, “Femininomenon” is the song, and it’s one hell of an album opener (it’sfound its way into a teaser trailer, too). You have to have some serious confidence to put a song like this as the first one on your album, but Chappell Roan has never lacked confidence. And she makes all the ridiculous parts of “Femininomenon” not only work, but soar. If you’re not locked in for the 13 tracks to come after hearing this… you’re a lost cause.Go listen toThe Eaglesor something, dude.
Anyway, “Femininomenon” hasengines revving, points in the song where everything stops so Roan can say something along the lines of, “Dude, can you play a song with a f**king beat?” to herself(?), and lyrics featuring lines like: “Hit it like rom-pom-pom-pom” and “Get it hot like Papa John.” There’s also a call-and-response part featuring no one but Chappell Roan calling and responding to herself. And the song gleefully celebrates women being better at sex than men, disses casual sex/“online love” several tracks before “Casual,” and proves gloriously campy from start to finish. If you want a near-perfect mood-setter for an album likeThe Rise and Fall of a Midwest Princess, this is it. You will get hot like Papa John and like it, dammit.
5"Pink Pony Club"
Released: July 10, 2025
There’s an argument to be made that “Pink Pony Club” is Chappell Roan’s signature song, or at least a contender. It has lyrics that reference Roan’s own experiences whilevisiting a gay bar in 2018, so it’s got the LGBTQ side of her artistry front and center. It’s more empowering and less explicit than “Casual,” too, which was more about the heartbreaking side of things. This one is more of an anthem.
But “Pink Pony Club” also succeeds in being a little mellower than Roan’s other anthems. Itbegins slow, and builds in intensity, so it bridges the gap between the ballads and bangersfound onThe Rise and Fall of a Midwest Princessextremely well. It was also first released as a single long before any other well-known Chappell Roan song, first coming out in 2020 (and gaining more recognition by 2023/2024). It’d be one of the most enjoyable songs to sing along to live, too, and its introspective yet hopeful lyrics make it difficult to resist overall.
4"Hot to Go!"
Released: August 21, 2025
See, the difficult thing about calling “Pink Pony Club” Chappell Roan’s signature song is that one has to then consider how to go about describing “Hot to Go!”, given that’s another contender for the title of “signature song.” And, like, there are a handful of songs debatably even better than this one. It boggles the mind.The Rise and Fall of a Midwest Princessis genuinely too good. So much to wrap one’s head around. Too much good pop. Too many hooks. Help!
If it weren’t for “Femininomenon,” “Hot to Go!” would probably be the silliest and most unapologetically poppy song on the entire album, butthat’s not intended to be a condescending comment. Roan knows how to turn silly camp into anthemic and cathartic pop music bliss. You want a hot take? Roan’s much better at doing that than Taylor Swift was when she was in her 20s, since her sillier pop songs from the 2010s, like “Shake It Off” and “Look What You Made Me Do,” can be kind of grating. But back to Roan, she got away with spelling out the title multiple times in a song in the year 2023, with “Hot to Go!” It shouldn’t work, but it does. To cut a long story short: spelling with Chappell Roan ismuch more fun than spelling with Swift.
3"My Kink Is Karma"
Released: August 06, 2025
“My Kink Is Karma” is about arelationship ending, and it’s astoundingly brutal and nasty. Honestly, this one can be almost unenjoyable to listen to, even though that chorus is so beautiful (it’s got the strongest hook out of all the slower songs onThe Rise and Fall of a Midwest Princess, by far). It is about feeling oddly good after a difficult break-up, and finding some degree of pleasure in seeing one’s ex struggling and falling apart.
It’s not subtle. After all, the song opens with the line, “We broke up on a Tuesday,” and the chorus states, “People say I’m jealous, but my kink is watching you crashing your car, you breaking your heart, you thinking I care.” And it doesn’t look as great if you’re just reading those lyrics, but it’s the delivery that makes it work. To be perfectly blunt, if you’ve felt twisted happiness after coming out of a relationship and seeing someone potentially hurting, the song hits hard. And, if you feel you’re the one doing worse after a breakup, and that the other person could be in Roan’s position, as in possibly not caring… like, damn. It’s so blunt, but also so gutsy. It’s one of the most confident songs on Roan’s debut album and, if you’re reeling from a break-up, potentially the most brutal. Pop music rarely cuts this deep. So, yeah, it’s one of her best. It tops “Hot to Go!” and “Pink Pony Club.”This song is something special. Awful, horribly, uncomfortably special, sure, but special nonetheless.
2"Red Wine Supernova"
Released: July 13, 2025
And on the complete other end of things to “My Kink Is Karma,” here’s “Red Wine Supernova.” This song, as track #2, follows on from the ridiculously high-energy “Femininomenon,” and if you’re listening toThe Rise and Fall of a Midwest Princessfor the first time without having heard any of the songs individually, you might be wondering how a song could follow on from that one and work. “Red Wine Supernova,” fortunately – and funnily – enough, is no ordinary song. In one fell swoop, it confirms that the offbeat and catchy euphoria of “Femininomenon” was no fluke.
“Red Wine Supernova” is a reassuring hug of a song, informing you that the entire album to follow will be a wild ride in the best of ways. It is also the best song on the entire album, and is just a perfect pop track. That’s a boring way to describe it, but that’s also the best way to describe it. It’s so bubbly, so many lyrics are quotable, andthe first verse is already catchier than most choruses could ever dream of being. The pre-chorus is even better, and then the chorus, complete with the title drop? Just impeccable. That Chappell Roan can make one of the best songs of the 2020s so far also have lyrics like “I’ve got a wand and a rabbit, so baby, let’s get freaky, get kinky, let’s make this bed get squeaky” is a testament to the fact that she’s a once-in-a-generation talent. Oh, andit’s got a pretty good music video, too.
1"Good Luck, Babe!"
Released: June 28, 2025
See,The Rise and Fall of a Midwest Princesswas already incredibly exciting, given the whole “it was a debut album” thing and all. It has some of the best pop music of the last few years on it. The best songs are fun in isolation or on playlists, but it’s also a largely coherent listen from front to back. Butthe story of Chappell Roan’s riseis incomplete without proper appreciation given to “Good Luck, Babe!”. This is the one. This is the song. It dilutes everything perfect about all the best songs on her debut album into one single. And what a single.
How do you even do this song justice with words? How does Roan borrow so heavily fromKate Bush(and in a post-Stranger Thingsworld, at that) and 100% get away with it? How does the chorus get better every time you hear it? That bridge that ends with her basically screaming, “You know I hate to say, but I told you so,” and then the way that desperation finds its way into the final chorus, all followed by the song basically breaking down and running out of steam in its final seconds, but in a way that works? Oh, and of all the Chappell Roan songs about love, sex, and heartbreak, this one hits the hardest… well, it’s on the same level as “My Kink Is Karma.” But it has that lyrical intensity coupled with a hook that’s even catchier than the most ear-wormy parts of “Red Wine Supernova.”That’s why this song feels like a refinement of everything great Roan’s done to date; it perfects what already felt borderline perfect. The best song of the 2020s so far? Honestly, maybe! “Good Luck, Chappell,” when it comes to topping this, because this is about as good as pop can feasibly get.
