Connecting Taylor Swift’s ‘Midnights’ With 13 Songs From Her Past

Dear listeners,

This past weekend, along with more than 200,000 people in the New York metropolitan area, I attended Taylor Swift’s Eras Tour. I saw sights I will never forget: more than one person, in late May, dressed head to toe as a Christmas tree (an inside joke about Swift growing up on a Christmas tree farm … I think?); a father proudly wearing a handmade shirt that read “Real Men Listen to Taylor Swift”; enough sequins per square inch that, when the sun hit it right, MetLife Stadium could probably be seen from space.

But, of course, I also saw a generation-defining pop superstar performing at the top of her game, throughout a sprawling, near-three-and-a-half-hour set that highlighted her stylistic versatility, physical stamina and ongoing evolution as a songwriter.

Though Swift has long had a flair for both spectacle and intimacy in a live setting, what I couldn’t shake (shake, shake) during this marathon 45-song set was how completely she’s come into her power as a performer. She knows how and when to ham it up — like the frequently memed moment when she gives her flexed biceps a kiss before donning a sparkly blazer for the synth-pop statement “The Man” — but she also knows when to scale back, as she does during the beloved segment of the show when she accompanies herself on guitar and piano and plays two “surprise songs.” (Not to brag, but I got to see “Holy Ground” and “False God.”)

In his review of the Eras Tour’s opening night, my colleague Jon Caramanica called Swift, rightly, “pop’s maestro of memory.” The “eras” conceit of the tour allows Swift to reflect on and momentarily embody her past selves; “Are you ready to go back to high school with me?” she asked playfully before her 2008 hit “You Belong With Me.” But she does something similar on “Midnights,” her latest album and the one that feels most directly in conversation with her own vast back catalog (which I noted in an essay shortly after the LP was released).

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.

Feel free to make your own expanded version of “Midnights” — I found it a fun exercise! — but I’m a mastermind, and this one’s mine.

You’re on your own, kid,

Lindsay

The Amplifier Playlist

Listen on Spotify. We update this playlist with each new newsletter.

“Midnights (Lindsay’s Version)” track list
Track 1: “Love Story (Taylor’s Version)”
Track 2: “Lavender Haze”
Track 3: “Welcome to New York”
Track 4: “Maroon”
Track 5: “You Belong With Me (Taylor’s Version)”
Track 6: “Anti-Hero”
Track 7: “Enchanted”
Track 8: “Snow on the Beach” (featuring Lana Del Rey)
Track 9: “Nothing New (Taylor’s Version)” featuring Phoebe Bridgers
Track 10: “You’re on Your Own, Kid”
Track 11: “Teardrops on My Guitar”
Track 12: “Midnight Rain”
Track 13: “How You Get the Girl”
Track 14: “Question …?”
Track 15: “Bad Blood”
Track 16: “Vigilante ___”
Track 17: “Tolerate It”
Track 18: “Bejeweled”
Track 19: “Treacherous (Taylor’s Version)”
Track 20: “Labyrinth”
Track 21: “Mean”
Track 22: “Karma”
Track 23: “Peace”
Track 24: “Sweet Nothing”
Track 25: “Blank Space”
Track 26: “Mastermind”

Bonus tracks

As I mentioned, Swift played some top-notch surprise songs at the show I attended. If you don’t believe me, crank them up: from “Red,” the ecstatic, guitar-driven fan-favorite “Holy Ground,” and from “Lover” (anywhere from my second to my fourth favorite Swift album, depending on the day you ask me) the slick, slinky “False God.” Darling, it was good.