Weeklist Special: Taylor's Weirdest Songs

We’re less than a week from the release of THE TORTURED POETS DEPARTMENT, the all-caps eleventh Taylor Swift album. We still don’t know what it will sound like, but it’s fun to imagine Taylor leaning into the weirder side of her personality. I love when Taylor gets weird; it’s one of the reasons why Midnights worked so well for me. But folks, Ms. Swift has always been weird. Here’s a playlist that I’ve curated of what I think are her weirdest moments. (Apologies if the Apple link has the songs out of order. I’m not sure why it did that!)

Picture to Burn – Taylor Swift

Taylor Swift’s debut record is a fascinating collection of all the possible directions Taylor could have taken her career. Sure, some songs serve as blueprints for what was to come, notably “Our Song,” but then there are songs like “Picture to Burn,” a track of a style she’d never attempt again. The song is clearly influenced by the fiery revenge tracks that flooded country radio at the time, from artists like Gretchen Wilson and, more importantly, Miranda Lambert. You can draw a straight line from “Kerosene” to “Picture to Burn.” The song is also infamous for its “Homophobic Version,” as the fans call it, where Taylor tells her male chauvinist target that she’ll tell her friends “(He’s) gay.” Needless to say, this is a standout in her catalog.

Message in a Bottle – Red (Taylors Version)

The Red era is famous for being Taylor’s first foray into pop music, though I’m of the opinion that from Fearless on, she was already writing pop. It’s a construction thing, not an aesthetic! Anyway, the album featured her first collaborations with pop master Max Martin, including smash hits “22” and “I Knew You Were Trouble.” “Message in a Bottle,” a From the Vault track revealed in the Red’s Taylor’s Version rerelease, is supposedly the first Martin-Swift penned track, and from the first verse you can see why it was left out from the original release. While the Red singles have a pop sensibility, they still hew closely enough to Taylor’s “country” sound that they don’t stick out too much. “Message in a Bottle,” however, would have been quite the sore thumb. Red’s pop leanings were already scaring Tay’s label Big Machine, so it’s easy to see why this was a bridge too far. The song itself? Not bad, though the chorus easily bests the wordy, first draft-y verses.

Better Than Revenge – Speak Now (Taylor’s Version)

Second only to “Picture to Burn” in the “problematic Taylor lyrics” category, “Better Than Revenge” is Tay’s tribute to Paramore’s “Misery Business.” The pop punk classic has its own baggage, both songs stamped with the slut-shaming and internalized misogyny that were typical at the time. Both Taylor and Paramore’s Hayley Williams have since said they regret the lyrics, but Taylor went the extra mile and re-wrote the line in question for her rerelease. Controversy aside, the song itself is also an outlier, full of hard guitar and punky sass. Taylor’s been on the record about pop punk and emo bands being a huge influence on her songwriting, and here the proof is in the problematic pudding. I especially recommend the amped up, no holds barred Taylor’s Version release, even with the more anodyne lyrics.

The Archer – Lover

To me, there are two Taylors; no, not the Old Taylor and the one that debuted with “Look What You Made Me Do,” but the pre-Lover Taylor and post-Lover Taylor. Not only is Lover her first record outside of Scooter Braun’s empire, but also the record that has “The Archer.” The song is an ode to her star sign, Sagittarius, and is the first song that sees Taylor in true self-analysis, self-deprecation mode. Sure, Taylor’s been introspective before, but usually about her innocent childhood (“Fifteen,” “Never Grow Up”), not her own, adult fragility. Here Taylor’s repeated line “Can they see right through me?” turns into “I see right through me,” a striking portrait of impostor syndrome. You can see a lot of this in her Netflix documentary Miss Americana, which delves into the self-doubt that she dealt with during her reputation era. The vulnerability shown in “The Archer” opens the door for later Taylor songs, including “Peace” and, more importantly, “Anti Hero.” The song also sees Tay taking a sonic leap as well; the droning synths and lack of any real melodic chorus is reminiscent of LCD Soundsystem’s classic “All My Friends” or the contemporary “Young Enough” from indie band Charly Bliss. It’s fun to imagine 18 year old Taylor shouting “Where are your friends tonight?!” at a karaoke party.

Untouchable – Fearless (Taylor’s Version)

“Untouchable” is early proof of Taylor’s expansive music taste. The song is technically a cover, a heavily rewritten and reinterpreted cover, that is, of a song by little-known band Luna Halo. The original recording is so different, you’d be forgiven if you assumed that this was a Taylor track. The chorus is largely the same, and you can see why Tay was so drawn to it—it’s big, dynamic, and addictive. The most killer moment is when she takes the harmony line for the last round and then lets the song coast away. Not necessarily a sonic outlier, but certainly a weird origin story.

tolerate it – evermore

Now that it’s the undisputed critical darling of her career, folklore doesn’t feel as radical as it did when it first released back in 2020. Aaron Dessner’s production, with its acoustic charm and electronic pitter-patter just feels like part of Taylor’s DNA now. This is mostly why I don’t have any folklore tracks on this list; as time passes, they just feel like Taylor Swift songs. evermore, however, has a few standout songs that feel like Dessner really helping Tay expand her horizons. One of these is “tolerate it,” her ode to the classic novel Rebecca, and an experiment in time signature. I love the ebb and flow of the verses, and the bridge is one of the most tense in her songbook. Most of all, though, I love that a pop star as gigantic as Taylor can write a song like this, a genuinely weird ballad about an old book that defies pop sensibilities. Just like “The Archer,” this is a song that opens the door for a few other sonic experiments, including a couple later on this list.

All Too Well (10 Minute Version) – Red (Taylor’s Version)

No, the original “All Too Well” is not weird. In fact, it may be Taylor’s signature song, featuring all of her hallmarks in their ideal form. The ten minute version featured in Red’s Taylor’s Version rerelease, however, is pretty weird. It takes the original and adds new verses and an entirely new outro to create a strange, Frankenstein ballad of enormous proportions. While Taylor had teased for years that there was a longer, profanity-laden version of the song on some papers somewhere, I’m not sure any of us thought it would be as exhaustingly emotional as the final result. The song’s dramatic length calls to mind forbears like “Bohemian Rhapsody” and “Welcome to the Black Parade,” complete with its own lighters up finale.

False God – Lover

While the reputation era gave us a peek, “False God” is where Horny Taylor officially made her debut. This sexy and sax-y song cements that not only did she grow up with alt rock and country bands, but she definitely had R&B in her rotation, too. Tackling such a traditionally Black genre like this is a risky move, especially for an artist as blindingly white as Taylor, but “False God” is certainly more convincing than her stab at rap, “End Game.” This may be why she hasn’t returned to this vibe since, but only time will tell. Oh, but back to the horny of it all – “The altar is my hips??” This ultimately leads to the Eras Tour chair dance to “Vigilante Shit.”

When Emma Falls in Love – Speak Now (Taylor’s Version)

“When Emma Falls in Love” is not a cover, but it’s a Weird Al-esque style parody, for sure. Here Taylor takes “Drops of Jupiter” by Train, a song she covered at live shows around this time, and re-engineers it as her own. Sometimes the similarities are eerie, like the way she sings “chay-ee-aaange” near the end. It’s the audacity of it that really endears me to it, but the fact that it may or may not be about Academy Award winner Emma Stone is the cherry on top.

Glitch – Midnights

Midnights is a weird record—it might be the strangest of her career. It’s largely a return to pop after folklore and evermore, but it maintains some of Aaron Dessner’s affinity for dying robot sounds on the periphery. “Glitch,” a bonus track featured on the “3 AM Edition” release, has so many of these sounds that its borderline hyperpop, without fully taking the plunge. I’d love Taylor to join the PC Music roster or collab with 100 gecs, but I know it’s never going to happen. But least we have “Glitch.” Also, a special shoutout to Tay’s delirious delivery and the creepy backup vocals. Again, the fact that the biggest pop star on the planet can make stuff like this never ceases to amaze.

New Romantics – 1989 (Taylor’s Version)

Fine, it’s not that weird. “New Romantics” is just a pop song amid the sea of stellar pop songs on 1989. But let’s get one thing straight: It’s the captain of the ship. “New Romantics” is such a great song it barely tracks as Taylor—its relegation to Bonus Track status on the original release seems to back that up. I love how propulsive it is; it’s the closest her catalog has to an EDM banger (at least one not recorded by Rihanna). Yes, it has some similarities to its younger sister “Starlight” from Red, but this one has a chip on its shoulder. The “New Romantics” show off their Scarlet Letters; they’re not teaching kids how to dream any time soon.

Sad Beautiful Tragic – Red (Taylor’s Version)

Taylor, like all of us, loves Mazzy Star. “Fade Into You” is an absolute classic, and “Sad Beautiful Tragic” features her best Hope Sandoval impression. Sure, later she’d channel a bit of this vibe for “Lover,” but she nailed it the first time. This is a bit of a divisive track for some fans; its slow pace and whispery delivery can bore the uninitiated, but if you let yourself… fade into its charms, it’s one of Taylor’s best ballads. I personally love the raw heartbreak you can hear in the Taylor’s Version rerelease. Truly, what a decade can do to a person.

New Year’s Day – reputation

Sometimes I wonder if we will ever get a fully acoustic Taylor record; just guitar and piano, like her demos. We’ve gotten a smattering of these over the course of her career (“Forever and Always,” State of Grace”), but “New Year’s Day” stands alone on her proper albums. As a result, it’s the most striking song on reputation—a sparse ballad following almost an hour of trap beats and synths. The piano line here is so memorable, Olivia Rodrigo borrowed it wholesale for her song “1 step forward, 3 steps back.” The empty space and reverb here only emphasize the desperate plea at the end: “Please don’t ever become a stranger whose laugh I can recognize anywhere.”

It's Nice to Have a Friend – Lover

Near the end of Lover, Taylor takes us on an island detour. “It’s Nice to Have a Friend” is one of the most divisive tracks on what might be her most divisive album (that’s not named “ME!”). I actually like it; its blissed out vibe is an interesting experiment for the usually Type-A Taylor. Thematically, it’s also odd; it’s ultimately a love song, but it starts with a story of childhood friendship. I’m borrowing from Rob Sheffield here (aren’t we all?) but you can draw a parallel to The White Stripes’ “We Are Gonna Be Friends” in all its innocent playfulness.

closure – evermore

It’s certainly a choice to start a song with clanging percussion, and it’s an even more ridiculous choice on an album full of quiet introspection like evermore. This is why this song generally has a negative reputation among Swifties, but I’m personally a big fan. I think Taylor should lean into the noise (see “Glitch,” above). But that’s just the beginning; the song proceeds to warp and change Taylor’s voice in some wild ways, effects that remind me of Kacey Musgraves’ “Oh What a World” or Vampire Weekend’s Modern Vampires of the City. It’s adventurous for her, and further proof that she’s weirder than we give her credit for.

Ronan – Red (Taylor’s Version)

“Ronan” is not actually that weird, but it is really, really sad. In a catalog as heart-wrenching as Taylor’s, it might be her saddest. Sure, “Soon You’ll Get Better” and “epiphany” are close runners up, but “Ronan” has it beat in pure specificity. In case you don’t know, Taylor wrote the song based on a blog written by a mother whose son died of cancer at the age of four. Many of the lyrics reference things that she wrote about in the blog, and as a result, the mother has writing credit on the song. It’s just brutal to listen to, and considering Taylor was only 22 when she wrote it, she channels a heartbroken mother extremely well. Bonus: The line “And it’s about to be Halloween, you can be anything” directly inspired Phoebe Bridgers’ Punisher track “Halloween.”