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Thirteen Things We Absolutely Do Not Know About Taylor Swift’s ‘Midnights’

Taylor Swift shocked the world this week, by spilling a little secret at Sunday night’s MTV Video Music Awards. “I thought it might be a fun moment to tell you that my brand new album comes out October 21,” Swift said. “And I will tell you more at midnight.” A few minutes later, she dropped her note about Midnights, with a photo of Taylor cradling her head in her hands, with a touch-tone phone, a Rolodex, and two empty ashtrays.

So all week, time won’t fly — it’s like we’re hypnotized by it. Midnights is the biggest mystery in the music world right now, and all fans can do is ask questions. How foolish we were to think Dr. Swift would let August slip away like a bottle of wine. Instead, she drank down this whole cruel summer in one gulp, and smashed the bottle at her feet. She timed her album reveal for almost exactly five years after she announced Reputation — five years ago, or in Taylor time, “Six Number One albums ago.”

Everybody moved on. I stayed here. So here are some of the burning questions around Midnights. Every day, she keeps sprinkling hints and clues like glitter eye-shadow. And every day, the fan folklore gets deeper as Swiftologists try to decode them, like we’re all passing notes in secrecy. But nobody knows a thing until Oct. 21, when Swift comes down from her mountain-top with the New Tay-stament. 

So here are 13 of the lingering questions that will keep us up for the next seven weeks. Meet me at Midnights.

1. Why, Taylor? Why?

Always the key Taylor question. Why does she do this to us? She doesn’t need to work so hard at dropping chaos on our heads. She just loves the game.

Taylor dropped off the radar this year, while making Midnights. But she made a rare public appearance in June at the Tribeca Film Festival, to present her short film for “All Too Well.” She got her biggest laugh when she admitted, “People often greatly underestimate how much I will inconvenience myself to prove a point.” 

Truer words, Taylor. And never underestimate how much she’ll inconvenience the whole world for a little album drama.

2. What is Midnights all about?

Taylor summed it up in her missive. “We lie awake in love and in fear, in turmoil and in tears,” she wrote. “We stare at walls and drink until they speak back. We twist in our self-made cages and pray that we aren’t — right this minute — about to make some fateful life-altering mistake. This is a collection of music written in the middle of the night, a journey through terrors and sweet dreams. The floors we pace and the demons we face. For all of us who have tossed and turned and decided to keep the lanterns lit and go searching – hoping that just maybe, when the clock strikes twelve … we’ll meet ourselves.

“Midnights, the stories of 13 sleepless nights scattered throughout my life, will be out Oct. 21. Meet me at midnight.”

So many questions, right down to the “sleepless nights.” She sleeps? 

3. Why October?

Midnights drops in the most Swiftian of months, exactly ten years (and one day) after Red, which arrived on Oct. 22, 2012. It’s her first Swiftober album since 1989. She broke her long-running tradition when she dropped Reputation in Nov, 2017, so it’s a symbolic return. Maple Latte Autumn is back, baby.

4. What the hell is going on in that album cover? 

Taylor is playing with a cigarette lighter, in front of a shower curtain. She’s staring at the flame, as if as if she’s lighting a goddamn blaze in the dark. It looks like Tay’s spending a lost weekend at the Midnights Motel in the Seventies, wearing a winter coat in the bathroom, with a fuzzy ruff. Taylor gazing at the lighter with blue eye-shadow naturally evokes her question in “All Too Well”: “Did the twin flame bruise paint you blue?”

Why does Taylor have a lighter? She doesn’t smoke and never sings about cigarettes, though sometimes she smells smoke after an emotional trash fire, as in “Daylight” or “Cardigan.” But she’s got two ashtrays on the table, plus a framed photo of two people. Is this just another picture to burn? 

The album artwork comes straight from the Ultra Chilled series of dance compilation CDs from the early 2000s. It spun off into Ultra Trance, Ultra Electro, and Ultra Rock Remixed, but for some reason the Ultra Chilled CDs are the ones I kept. Does this mean Taylor is going for a laid-back electro Ibiza hangover vibe? Just looking at the cover gives a “hey, it’s Wednesday after Coachella, where did everybody go?” buzz.

The font is amazing, too — she’s making a hard swerve away from the elegant serifs that defined her Folkmore era. A case-sensitive sans-serif font? A bold new choice for her.

5. These new photos are…a lot, right?

Taylor’s got four different covers for the vinyl editions: Blood Moon, Jade Green, Mahogany, and Midnight Blue. She’s in a room with a heavy Seventies motel vibe: wood paneling, sickly green carpet, shaggy curtains, the works. It looks like it got decorated by Carol Brady after a few Harvey’s Bristol Creams.

In one photo, she just put on glitter eye-shadow to have a weepy meltdown, which is a very Taylor move. She lounges with her feet up, with proggy-looking vinyl LPs on the floor. Nothing good has ever happened in this room. I can’t help thinking it’s the sleazy motel from “Getaway Car,” maybe even the one with the parking lot in “Illicit Affair.” 

That keyboard in her room? It’s the ultimate 1970s keyboard, a vintage Wurlitzer, famed for stoner epics by the likes of Supertramp and Three Dog Night. But you’ve heard it from Ray Charles (“What’d I Say”) to Queen (“You’re My Best Friend”) to Daft Punk (“Digital Love”). Taylor had the Wurlitzer on Folklore (“Betty”) and Lover (“Soon You’ll Get Better”). Will her Wurlie be on the album? Or is it just a cool place to stash yet another ashtray?

6. What about the vinyl?

It’s a huge tell that she’s dropping the vinyl on October 21, the same day as all the other formats. (Yes, she’s releasing it on cassette, and yes, I smashed that pre-order link like Este hitting the Olive Garden breadsticks. I swear Folklore and Evermore sound best on cassette.)

It’s a single vinyl LP, so it’ll max out at about 22 minutes per side, which is new for her. Folklore, Evermore, and Lover were all an hour long. Rep was 56 minutes. The only album she’s ever released at vinyl length (since her debut) is 1989, which is 48 minutes. (Roughly as long as Kind of Blue, Astral Weeks or The Velvet Underground and Nico.) Taylor likes to drop an hour of music at a time — that’s her comfort zone. But 13 songs in 48 minutes means they average under four minutes, which is Folklovermore-size rather than Speak Now-size. Put it this way: expect Midnights to be less than five “All Too Well”s long.

7. Will this album involve heartbreak, turmoil, betrayal, and tears?

Are you new here? It’s a Taylor Swift album. When she came out of her work bubble for the Tribeca Film Festival, she made a revealing comment, quoting the indie legend John Cassavetes: “I’ve never seen an exploding helicopter. I’ve never seen anybody go and blow somebody’s head off. So why should I make films about them? But I have seen people destroy themselves in the smallest way.” Swift added, “I felt that.”

So brace yourself. If there’s anything we know for sure about Midnights, it’s that people will destroy themselves in the smallest ways.

8. Why is this album about midnight, not 2 A.M.?

Everybody knows how much Taylor loves a crisis at 2 A.M. That’s her favorite time for walking the floor, wishing you were at her door, cursing your name, riding in your truck, feeling like she lost a friend, or just missing you while headlights pass the window-pane. She has some of her finest meltdowns at 2, though she switches it up in “Last Kiss” by seeing her ex’s face at 1:58. But whenever she chooses her moment, to paraphrase Laura Palmer on Twin Peaks: Night time, Tay time.

9. What does midnight mean on Planet Taylor?

She’s always got a special thing for midnight. That’s when she gets picked up in “Style,” when she has breakfast in “22.” She wants your midnights in “New Years Day.” She has an rotten time at midnight on her 21st birthday (in “Happiness,” “The Moment I Knew,” and “All Too Well”). When you pre-order Midnights at her official shop, there’s a joke about “22”: “It feels like a perfect night…to join our list!” 

But my favorite Taylor midnight scene is the extremely underrated bridge of “The Last Great American Dynasty,” the moment where Rebekah paces the beach by night, “staring out at the midnight sea.” It’s the one moment in the song where Rebekah is alone, and it’s the moment where we see how horribly lonely it is to be the town widow when her fair-weather friends have drunk up her champagne and left her behind. Midnights seems poised to go deeper into that kind of loneliness.

Note: Since “midnight” is the opening word of “Style,” this might be the place to mention that Midnights drops the same day My Policeman opens in theaters, October 21. So you can begin your day with Taylor’s new album and end it with Harry Styles’ new film, if that’s a random combo you happen to be into.

10. What about the Emily Dickinson connection?

Taylor signs off her missive with the words, “Keep the lanterns lit and go searching… We’ll meet ourselves.” The Emily Dickinson stan account @emilysorchard points out that this evokes a letter that Dickinson wrote in 1855, telling a friend, “I am out with lanterns, looking for myself.” Later in the same letter, Dickinson writes, “I can’t help laughing at my own catastrophe,” and what a Taylor line that is.

The Tay-Emily affinities run so deep. She revealed her 19th-century poetry fetish in 2020 with “The Lakes,” singing about Wordsworth and Coleridge. At the time, I wrote, “Tay should keep it going with the lit fan-fic — maybe Emily Dickinson or Gertrude Stein next?” So I’m obsessed with the hope for more Belle of Amherst content. Dickinson was very into writing about midnights, from “Good Morning—Midnight” to “Dreams—are well—but Waking’s better” to “We grow accustomed to the Dark,” all poems that any Swift fan would love. Here’s to Wild Nights! Wild Nights! (Taylor’s Version).

11. When is the next Taylor’s Version?

Everybody figured she had another TV coming this year. The mystery was: Speak Now or 1989? She kicked off her summer in May by dropping “This Love (Taylor’s Version),” remaking the killer 1989 ballad. The same day, she added “The Old Taylor Collection” to her store, full of Speak Now and 1989 merch. Was she just setting us up to throw us off the scent?

12. Where are Jack Antonoff and Aaron Dessner?

Taylor hasn’t said a word about producers, or whether she’ll keep working with her two trusty collaborators, the dynamic duo of Jaaron Desstonoff. This team has chemistry, as you can see in her Long Pond Studio Sessions. It’s like the creative trio behind David Bowie’s Berlin Trilogy: Jack is her Brian Eno, Aaron is her Tony Visconti, with Tay as the devious blonde mastermind.

One thing we do know: she’s picky about producers, and when she clicks with one, it’s not the kind of connection she typically walks away from.

13. Is Taylor going for more cottagecore? Or is she heading back to pop glitz?

Taylor wrote the greatest songs of her life with Folklore and Evermore, where she got into acoustic guitar and mossy cabins. Back in June, she dropped a fab new folkie ballad: “Carolina,” from the film Where The Crawdads Sing, one of her most awesomely creepy night-prowler songs. Time will tell if “Carolina” was her farewell to the Folkmore era, or a bridge to her next glossy synth-pop album.

But let’s put it this way: has she ever made three albums in a row with the same musical theme? Even when it’s what people are begging for?

We already know from her note that Midnights is full of late-night insomniac misery. (Thank God.) It’s not going to be a cheery listen. But remember, her cottagecore albums were inspired by the pandemic, which meant no live shows. She wrote those songs knowing she wouldn’t be rocking them in stadiums full of confetti and dancers. The scene will be different in 2023, and if she’s planning to tour, she’s going to write some pop stadium bangers. The once-maligned Lover is having a huge year — it’s her highest-charting, biggest-streaming album each week, and “Cruel Summer” has gotten so iconic, it now looks like a brilliant move that she didn’t make it a single. (She plans everything.) But so far, she isn’t tipping her hand about Midnights

Taylor loves to keep people guessing her next move, and she loves it when we all fail. So casually cruel, in the name of nothing at all — just for the hell of it. She’s already out to destroy our lives with this album and we haven’t even heard it yet. 

There’s a lot of midnights between now and Oct. 21. Good luck sleeping through any of them.

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