What Makes A Good Taylor Swift Surprise Song?

On Friday, June 9, Taylor Swift performed “Haunted” as her first surprise song. Walking up to the tip of the stage, her flowing magenta gown shimmering under the lights, she teased the upcoming arrival of Speak Now (Taylor’s Version), and launched into the breakup ballad. Afterwards, she switched over to the piano and without introduction began belting out Red deep cut, “I Almost Do.” By the end of those two songs, there wasn’t a dry eye in the house.

The Eras Tour surprise (or as some Swifties call them, “secret”) songs have become a big deal, and for good reason. For those who aren’t already familiar, Swift acoustically performs two different off-the-setlist tracks at every Eras Tour performance, with the intention of never repeating a song. These selections aren’t announced ahead of time — hence them being “secret” — so fans find out what she’s playing in the moment, as she’s playing them. (Swifties are nonetheless still trying to predict which surprise songs she’ll play each show by compiling huge spreadsheets that track which songs she’s played, and those she has yet to play.) They’re the sole part of her gargantuan, three-plus-hour-long extravaganza that’s spoiler resistant, so as you can imagine, they’ve become very special in the Swiftian Eras Tour lore.

Ask any Swiftie and they’ll tell you their unique wishlist of surprise songs. “New Romantics!” “Teardrops On My Guitar!” “Our Song!” “Cornelia Street!” (Most of these have already been played, by the way.) But what constitutes a good — or even great — surprise song performance? And are there potentially bad surprise songs?

Perhaps those who were in attendance on her third night at MetLife could speak on that last question. For that show’s surprise songs, Swift toted out an acoustic version of the already generally disliked “Welcome To New York,” a confusing and disappointing option for many reasons. It was her last night in the city, so there was nothing particularly “welcoming” about it. The song, which my friend who attended the show believes was secretly commissioned by New York City’s Division Of Tourism, hit a bit too on the nose; it’s the obvious choice. There’s nothing in the track one can really emotionally connect to, and whatever life the song’s exuberant synth production made up for on its studio recording was completely stripped away when Swift repurposed it as an acoustic guitar track.

Of course, “Welcome To New York” (among a select few others like “Me!”) is an outlier. Generally, any of Swift’s songs would make a good surprise song, but this made me think that perhaps timing, location, and other factors — like whether a song already has an established canon among Swifties — contribute to the excitement around surprise songs.

Take Swift’s choice of “Haunted” in Detroit. The show followed the singer’s official tracklist unveiling of Speak Now (Taylor’s Version), so having her perform a fan favorite from the album made complete sense. Similarly, Swift playing “Teardrops On My Guitar,” the song that broke her career, in Nashville, the city where she broke her career, was logical. The same can be said about “The Best Day,” Swift’s touching ode to her mother from Fearless, which she performed on Mother’s Day in Philadelphia.

Outside of context, the stories fans spin around certain songs help contribute to a song’s specialness. No wonder every Swiftie is dying to hear “Cornelia Street,” or “Sweet Nothings,” or “New Year’s Day” post-breakup with Joe Alwyn, as they’re songs inextricably tied to the English actor. Personally, my wish list included “Tim McGraw” and “Our Song,” two of her earliest hits, because who knows if we’ll ever get to hear those songs again after this tour?

The morning after the show at brunch, my friend brought up one more extremely crucial point about the surprise songs that stuck with me: The importance of that one, shoutable lyric, that one bridge, that one part of the song that turns a good live music moment into a transcendent, transformative one. When you’re standing in the dark with Swift — who’s holding just a guitar or sitting at the piano, no other distractions around — singing with the songwriter who wrote those words, it’s like none other. Think “Would’ve, Could’ve, Should’ve” and the thrill of 50,000 people screaming, “give me back my girlhood, it was mine first” in unison. Or the entirety of the bridge of 1989 hit “Out Of The Woods.”

Last Friday night on the floor of Ford Field, that resounding moment for us was the chorus of “Haunted,” which took on a different shade of grief in the aftermath of, well, you know what. Or maybe, it was the bridge of “I Almost Do,” that had the young teen in front of me screeching until her throat cut out. Really, it could’ve been any moment of those two songs because, who am I kidding, it was just incredible to be there.