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Repair common Windows errors and clear accumulated junk for a smoother, more stable PC - no reinstall needed.Free scan · no reinstallFor a first listen, start with “Pink Pony Club”; for the sharpest snapshot of Chappell Roan’s pop instincts, try “Good Luck, Babe!” This ranking weighs lyrical storytelling, vocal character, hooks, arrangement and emotional impact—not chart positions. It considers released songs through October 7, 2026, including album tracks and standalone singles, with the 14-song The Rise and Fall of a Midwest Princess as its center.
How this ranking works
There is no official ranking of Roan’s best songs. This is an editorial order, balancing the songs’ distinctiveness, songwriting, performance and ability to capture the mix of camp, intimacy and queer perspective that defines her pop. The album was released September 22, 2023, runs 49 minutes and moves between theatrical dance-pop and quieter ballads, according to Apple Music. Its story is closely tied to queer self-discovery: in the release announcement, Roan described it as “stories of unearthing my true self and fearlessly embracing queerness,” after four years of work, as reported by Universal Music Canada.
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The Rise And Fall Of A Midwest Princess | $11.60 | Buy on Amazon |
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![The Rise And Fall Of A Midwest Princess [CD]](https://m.media-amazon.com/images/I/414eF5RdmoL._SL160_.jpg)
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The Rise And Fall Of A Midwest Princess [CD] | $20.99 | Buy on Amazon |
| 3 |
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Chappell Roan - Icon of our Times | $21.99 | Buy on Amazon |
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Fame: Chappell Roan | $9.99 | Buy on Amazon |
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Chappell Roan - The Rise and Fall of a Midwest Princess | Piano/Vocal/Guitar Songbook for Fans and... | $14.98 | Buy on Amazon |
The songs below are ranked for their artistic impact, not sales or chart success. Album positions are included as a guide; the standalone singles are identified separately.
The 10 best Chappell Roan songs
1. “Good Luck, Babe!”
Roan turns a painful, unresolved relationship into a widescreen pop confession. The song’s emotional tension is its engine: its narrator sees what the other person refuses to admit, but cannot make that person choose honestly. Roan’s vocal performance gives the hook both ache and force, so the song lands as more than a triumphant singalong.
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Its construction took time. Producer Dan Nigro told Billboard that the idea began with Roan and Justin Tranter in November 2022 as a verse and chorus under the working title “Good Luck, Jane.” The collaborators returned to it and worked to find the chorus; Nigro recalled, “We kept on getting so frustrated.” That long development suits a song built around a feeling its narrator cannot simply resolve.
2. “Pink Pony Club” (album track 12)
“Pink Pony Club” makes the album’s central transformation feel vivid and specific: the pull of a stage, a new community and a self the narrator wants to claim. Its theatricality is not just decoration; the scale of the song mirrors the scale of the decision at its heart. It is an ideal entry point for listeners drawn to Roan’s big, emotionally open pop.
Rank #2
- Chappell Roan Records
3. “Red Wine Supernova” (album track 2)
Flirtation becomes a full-on rush in this bright, playful track. Its electro-psych coloring sets it apart from straightforward retro pop, while Roan’s delivery keeps the lyrics teasing and exuberant. Universal Music Canada describes it as country-pop, a useful reminder that Roan’s genre touches are often more fluid than a single label suggests.
4. “Casual” (album track 5)
Few songs in Roan’s catalog make an uneven relationship feel so clear-eyed. “Casual” centers on a friends-with-benefits arrangement and the mismatch between what one person wants and what the other is willing to name. The synth-pop setting keeps the track moving, even as its story turns on frustration and denial. Its strength is the contrast between a polished pop frame and a situation that feels emotionally lopsided.
5. “HOT TO GO!” (album track 7)
“HOT TO GO!” is Roan at her most immediate: a punky, cheer-like singalong designed around a hook that invites participation. Universal Music Canada describes it as a punky singalong, and that combination captures its appeal better than calling it simply dance-pop. The song’s playful simplicity is a craft choice, not a lack of ambition.
6. “Femininomenon” (album track 1)
The album begins with a feint: a mournful opening gives way to an insistent beat and a demand for pleasure and respect. That shift establishes Roan’s gift for turning theatricality into a point of view. The song is funny and forceful at once, and its abrupt changes make it a particularly strong introduction to the record’s sensibility.
Rank #4
7. “Kaleidoscope” (album track 10)
Against the album’s glossier, more extroverted tracks, “Kaleidoscope” makes space for vulnerability. Its acoustic-guitar arrangement keeps the focus on the feeling of a love that changes shape rather than vanishes cleanly. Universal Music Canada calls it an introspective acoustic-guitar ballad; it is one of the clearest demonstrations of how well Roan’s writing works without a maximal pop arrangement.
8. “My Kink Is Karma” (album track 8)
“My Kink Is Karma” turns resentment into a gleeful poison-pen letter. Its dance-pop pulse makes the narrator’s satisfaction in an ex’s misfortune feel wickedly light on its feet, while the writing gives that attitude enough specificity to avoid sounding like a generic breakup taunt. The track’s confidence and comic bite make it one of the album’s most distinctive character studies.
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9. “California” (album track 13)
“California” is a ballad about homesickness and frustration: the distance between where the narrator is and the life she expected to have. Its quieter scale makes it an important counterweight to the album’s club-ready songs. Rather than turning disappointment into a punchline or a victory lap, it allows the ache to remain unresolved.
10. “Super Graphic Ultra Modern Girl” (album track 6)
A sardonic opening monologue leads into a euphoric club song, a switch that makes the track feel knowingly larger than life. Roan’s wit is central to its momentum: the opening gives the dance-floor release a character and an attitude before the beat takes over. It rounds out the list as one of the album’s most playful examples of her theatrical pop craft.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Where the album’s other tracks fit
This list is a selection, not a verdict on the remaining songs. The full album’s sequence is “Femininomenon,” “Red Wine Supernova,” “After Midnight,” “Coffee,” “Casual,” “Super Graphic Ultra Modern Girl,” “HOT TO GO!,” “My Kink Is Karma,” “Picture You,” “Kaleidoscope,” “Pink Pony Club,” “Naked in Manhattan,” “California” and “Guilty Pleasure.” “Coffee,” a song about trying to close the loop with an ex, and “Picture You” offer different shades of intimacy; “After Midnight,” “Naked in Manhattan” and “Guilty Pleasure” extend the album’s playful, dance-oriented side. Apple Music’s album page provides the complete track listing.
Why the album is the center of the ranking
The Rise and Fall of a Midwest Princess is the most coherent foundation for a list of Roan’s best songs: its sequence moves from a theatrical demand for pleasure to ballads and club tracks without losing the perspective of its narrator. Its success is also part of its history, but not proof of its artistic standing. The Official Charts Company records a UK Official Albums Chart peak of number one and identifies it as the UK’s best-selling debut album on vinyl in 2024. Those are UK-specific chart and sales distinctions, not global measures of quality.
Roan’s Grammy win for Best New Artist in 2025 is further career context, rather than a reason to rank one song above another; the award was reported by the Associated Press. For background on her performance approach and experimentation, see the Recording Academy interview.
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