That brings me to today’s playlist. It is, essentially, my own expanded version of “Midnights,” placing each of its 13 tracks as a response to an earlier Swift song.
(Listen along on Spotify as you read, and find YouTube links below.)
Making your way through its 26 songs, you will hear how Swift’s songwriting, perspective on love, vocal stylings and aesthetic preferences have all evolved over time. The G-rated romantic of “Love Story” becomes the fed-up 30-something bristling at “the 1950s [expletive] they want from me” on the “Midnights” opener “Lavender Haze.” Swift’s adopted home of New York City goes from an idealized abstraction to the locale of a more specific heartbreak in the progression from “Welcome to New York” to “Maroon.” The pining narrator of “Teardrops on My Guitar” feels miles away from the wizened woman singing “Midnight Rain,” who has realized that love and marriage won’t solve all her problems. In the long arc of Swift’s chronology, “Enchanted” gradually becomes, well, disenchanted.
Evolutions in instrumentation and production choices emerge, too: not just how banjos and guitars morph into drum machines and synthesizers, but how much darker most of “Midnights” sounds even in comparison to her first “official” pop album, “1989.” Jack Antonoff produced both the bouncy “How You Get the Girl” and the later “Question …?”, which feels like a hazier and more melancholy variation on a similar theme.
In losing her illusions, though, Swift gains strength, perspective and resilience — not a bad trade-off. In “Nothing New,” a song she wrote when she was 22 and rerecorded with Phoebe Bridgers in 2021 for the rerelease of her 2012 album “Red” — she worries about the future; a decade later, on the incisive “You’re on Your Own Kid,” she tells her younger self, with earned wisdom, “You can face this.”
In the spirit of the Eras Tour, I hope this playlist stands as a testament to the depth and emotional acuity of Swift’s catalog. The specific connections between these songs will be a little easier to clock if you’re already a card-carrying Swiftie, but if you’re only familiar with one side of Swift, this playlist can also serve as a crash course in her many transformations.