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Truly one of the country crossover greats. Disco-tinged, effortlessly melodic, with Kacey’s iconic wit front and center.

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The charts are what’s embarrassing, tbh. In collaboration with Dev Hynes, Sky brought pop music to a screaming halt. To anyone paying attention, at least. It’s sparsity is its strength.

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Reputation was Taylor at the height of her imperial era – she was almost at the point of breaking through to an entirely new echelon altogether. This showcases her savvy and remains a pivotal moment in a pivotal career.

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Wow this melody is picture perfect. Plus, getting to scream, “Leave!” is fun every time.

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This is truly one of the greatest choruses and most underrated one hit wonders in all of pop. This is a work of art.

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The world was just not ready for BANKS when this dropped. An undeniable masterpiece that helped expand the idea of what a pop song could be… her influence is audible in many of today’s hits.

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When pop punk was building its dominance in the mainstream, Ashlee Simpson came in and brilliantly extracted all the parts that were resonating. Calling “Pieces of Me” punk is hysterical, but it is a bridge.

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Never forget it was Britney who put this on the Western map. An unrelated precursor to the K-Pop wave a few years later, but a stepping stone still.

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Billy Joel’s ties to the world of pop music are inextricable, even if he doesn’t offer much in the way of “pop star.” The doo-wop throwback “Uptown Girl” is so infectious, generations just keep discovering it.

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Paul was the pop star of the Beatles, and the pop star of the post-Beatles – and he was read for it. With Wings, he took the conversation about his penchant for crafting poppy love songs and…I don’t know, made his best one?

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