Molly's Top Taylor Song Guide, Part 1
Why I like the songs I like: An intro to T.S. for the uninitiated
In my last post, I promised a Molly’s Top Taylor Songs playlist, and not one to reneg on a promise (OK well, I’m sometimes one to reneg on a promise, but that’s mostly because I’m an Aries with a million ideas and boundless enthusiasm and more intention and desire than any mere mortal could ever follow through with, plus I have a chronic illness that makes follow-through quite literally impossible almost all of the time, but I never mean to reneg on a promise… anyway just go with me here…), here I present to you:
The one and only Molly’s Top Taylor Songs Playlist.
(Substack won’t let you embed playlists, only individual tracks, so click the link for the list.)
The original intention with this list was to introduce my favorite songs to my friend Liz, recipient of those original voice memos, or, in an abstract way, to anyone not familiar with Taylor but curious about why I like her. The idea is to help her/them/you hear what I hear and why, in the same way that original NPR radio show helped me appreciate 1989.
Which is to say this isn’t necessarily meant to be THE best Taylor song’s. But MY best Taylor songs. If I were devising a list for, like, a Taylor Swift 101 course, the playlist might look a little different. But this is coming from a more personal place.
Which is also to say, these are my favorite songs right now. My preferred tracks tend to change over time, depending on my mood, and on which song I’ve played on repeat so much I’m sick of it now, and which song I didn’t used to like but I suddenly re-discovered because it was in some T.V. show, or because the choreo on tour was cool, or I heard some backstory that made it more interesting or relevant to me.
Taylor has such a large and rich catalog, and I’m still so relatively new to her music, that I find my tastes within her oeuvre tend to change and shift more dramatically and more often than my taste with other artists, which, honestly, is part of the delight of being her fan and swimming around in her cinematic universe.
Like for example, as I mentioned in my last post, I used to be a very strong 1989 girlie, and not at all interested in the -ore’s, whether folkl- or everm-.
But just in the last few weeks, I’ve been really digging some of that folkie cottagecore early COVID sound, and so here we find ourselves with tracks from both folklore and evermore in the top 10. Who would’ve thought?
I am trying to narrow my list down to only 20 songs, but we’ll see if that happens. I’ve also already established a Slush List for the tracks I originally put on top and then moved, because of course I have. Perhaps I’ll share that one with you too.
For now, this is a living list that I’m actively honing as I’m also writing the little blurbs below about why I chose the songs I chose. First 10 in this post. Then another 10 (or more?) in the next post. I’m splitting it up this way for ease of reading, and also so I don’t spend 17 weeks “perfecting” this before sharing it with you.
What you have here is in no particular order, and definitely not in order of most to least favorite. It’s really just in order of what songs I most felt inspired to listen to and/or talk about, right this second. I’d love to hear what you think (including if you think these are all boringAF, as is your right, and at certain times I would’ve agreed with you), or what songs are your favorite.
Oh and a final thought before I dive right in.
I want to acknowledge, again, that this is a super intense time right now, and writing about this of all things might seem pretty weird.
And it is. But I’m finding it weird in a really good way.
On election day, I decided that I was going to be extra gentle to my nervous system. I didn’t have a specific buddy to watch the election with, and doing so didn’t seem like a stimulating or important or fun way to participate in collective culture or do my civic duty as much as a way to just opt in to a collective panic attack - a panic attack I didn’t want. I was uncharacteristically not interested in the dopamine rush or adrenaline surge of alllll of that business *waves vaguely towards the TV, the White House, the whole country* and so I made a choice not to engage in it until I felt up for it - which turned out to be never (so far).
I started the morning of November 5 listening to Taylor Swift, which then inspired to me to write about Taylor Swift, and that’s how I spent the entire rest of the day until I went to bed. No news shows. No newspapers. No checking social media for results. I didn’t even listen to non-news podcasts. Just music. And writing.
And what I felt was joy. And fun.
And yes, it felt kind of wrong to be feeling those things on such a terrible day.
But it also felt… good. And important.
As in, important that I stay as calm and regulated as possible for as long as possible, while things are still theoretical, while things are still building. Because when it is time to get to work, and respond to real emergencies, I’m going to need to be as resourced as possible. I need to not freak out until it’s actually freak out time.
And funny enough, that proved true the next morning, when the smell of smoke woke me out of a dream, and I had to summon my nervous system to help me pack and leave my house to escape a fire.
I found myself so grateful I wasn’t exhausted and strung out from anticipating the metaphorical fires to come, so that I had the mental and physical resources to face the actual real and present fire right in front of me, with as much clarity and focus and calm, and as little physical payback, as possible.
And so in that way, this Taylor Swift business, or whatever your Taylor Swift business is for you, feels very important indeed. May we all give our nervous systems the Taylor Swifts they require, so that when the coming danger arrives, we are fully rested, fully sharp, and fully ready and able to handle it.
And so here you go. A little bit of fun and diversion, from my nervous system to yours: Top Taylor, Part 1.
And we start with…
1. All Too Well (10 Minute Version) (Taylor’s Version)
Taylor has a reputation for putting vulnerable, personal, emotional songs in the Track 5 slot, and this epic break-up song about her relationship with Jake Gyllenhaal might be her best (and best known, and my favorite). It captures the rumination, perseveration, and haunting quality of the specifics of your memories after a difficult break-up - and the question of whether the other person remembers those same details and is haunted by them too.
The longer 10-minute version she released in 2021 with her re-recorded Red album (and also made an award-winning short film for, starring Sadie Sink of Stranger Things fame) especially captures that quality of being intrusively, repeatedly tortured by the same images over and over, with its driving rhythm and building intensity.
Every time I listen to this song, a different set of lyrics stand out to me. Today it’s:
And I was thinkin' on the drive down,
Any time now
He's gonna say it's love
You never called it what it was
This just feels like such a simple but heartbreakingly accurate way of expressing what it’s like to be in a situationship that feels more serious to you than the other person is treating it. This song is filled with gut punches like that.
Trivia: Taylor and Jake dated from about October 2010 to the end of that year, when she was 20 and he was 29. There is a red scarf referenced in this song that some people think is literal, but Taylor has said it’s a metaphor, and it’s speculated it’s a metaphor for her virginity (or perhaps her innocence). When her fans post red scarf emojis, especially on posts about Jake, that’s a reference to this song (and is a way of supporting her, and chastising Jake for breaking her heart). There’s also an actress referenced in the song - speculation is that was Anne Hathaway, Jake’s co-star in Love and Other Drugs. Also, Jake has become sort of notorious for dating much younger women, and for abusing his power in a predatory way. Check out “The Movie Star and Me” to see what was going around the zeitgeist in the #MeToo days.
2. Willow
God I love this song, though I don’t have a ton to say about why. I think a huge reason is the way Taylor interprets is visually on stage in the Eras Tour: just all witchy Stevie Nicks fairytale vibes. But there’s also that beautiful ascending bass riff, the rhythm that feels like it’s leaving you suspended in air, those harmonies…
Actually, the Wikipedia entry explains exactly why I like it, so might as well just copy and paste that here:
"Willow" is a chamber folk ballad with Americana stylings, indie folk orchestration, tropical house accents, and a hip hop-leaning rhythm reminiscent of Swift's 2017 album, Reputation. It is built around a glockenspiel, drum machines, cello, French horn, electric guitars, violin, flute, and orchestrations, and is characterized by its "breathless" chorus.
“ ‘Willow’ is about intrigue, desire, and the complexity that goes into wanting someone. I think it sounds like casting a spell to make someone fall in love with you.” — Swift, American Songwriter
CHAMBER FOLK?!?!? That’s even a THING? Sign. Me. Up.
Trivia: This song is from Taylor’s album evermore, one of two albums she wrote during the height of COVID in 2020. In those albums (this one and folklore), Taylor explores fiction and storytelling in a way she hasn’t on previous albums, including an entirely made-up relationship between made-up characters named after two of her best friend Blake Lively’s kids (Betty and Inez). Both albums have been critically acclaimed, though I didn’t listen to either until I watched the Eras Tour movie.
Bon Iver, Haim, and The National appear on the album. Also notable, she was dating and living with Joe Alwyn at the time. Though the albums are said to be entirely fictional, it’s also possible she was exploring themes about her relationship with Alwyn - and also possibly Matty Healy, with whom she’s had an on-again-off-again long-term thing since 2014 and then dated for real, briefly and painfully, after she and Joe broke up - in a way that she couldn’t talk about more directly (and non-fictionally) while still with him. Oh also, Joe co-wrote like 10 songs on these albums, under the pseudonym William Bowery. Some people think the songs he helped write, like “exile” and “betty” (which happens to be my friend Josh’s favorite Taylor karaoke song), are some of the albums’ best.
3. the 1
Okay so let’s just get out of the way that I kind of roll my eyes at texting grammar making it into song titles, but that’s an “OK, Boomer” battle I’ll never win, so I won’t say more about the fact that she doesn’t spell out the word “one” here.
What’s more important is what a profoundly catchy and compelling song this is. This track is from folklore, the first of her two COVID albums, and not coincidentally, the cottage core vibe and ascending arpeggios sound similar to what I like about “Willow.”
But what really gets me about this song is how it captures the wistful and also warmly fantasy-nostalgic feeling of musing about what it would’ve been like to date someone that you didn’t, or to have gone further with someone than you did (specifically if it was their choice that you didn’t).
I used to fantasize sometimes about what it would have been like if I’d stayed longer with one of my high school boyfriends - the romantic playwright Libra. If we’d lost our virginity to each other. If we’d reunited when older, and gave it a real shot. In my mind, there was a timeline where we had a beautiful love affair that somehow replaced some or all of my teenage trauma, or rewrote some of the failed relationships of my adulthood.
There have also been crushes, friends, unrequited loves (from my side or theirs) that I think about from time to time. The eternal what if.
Of course, there’s a reason those “if”s never became “is”es. But that’s not what this song is about. It’s about the feeling of the “if,” and feeling that feeling while, like, drinking a warm beverage in a cozy sweater next to a window overlooking a foggy forest. Yum. Chai tea and fantasy.
Favorite lyrics (today at least):
If one thing had been different
Would everything be different today?
Because really, who has not gone over and over what they could’ve done different, in that one conversation when I didn’t tell him how I really felt, or when I hooked up with his friend and he later said that’s why we couldn’t date, or when he met someone else first but what if he hadn’t…?
In my defense, I have none
For digging up the grave another time
But it would've been fun
If you would've been the one
Because it would’ve, wouldn’t it have? In the fantasy anyway…
4. So Long, London
I mean, if only for the intro alone…
Wikipedia calls it chamber pop, and well, hel-lo. Those layered harmonies made to sound like church bells? Maybe even the bells at Westminster Abbey? In London? C’MON…
But I love this song from The Tortured Poets Department (or TTPD) for more than just the intro. It is a heartbreaking, breathless anthem to being forced to leave a relationship because someone can’t show up in it, even if you don’t want to, and the deep pain and sadness and even anger that can bring.
There is a driving rhythm, paired with these haunting syncopated echoes and harmonies, and a contrast between racing-thoughts-speed verses and I’ve-made-up-my-mind measured choruses, and raw emotional vocal delivery that just fucking kills me. If I were debating whether to leave a lover, I don’t think I could listen to it. This and the last episode of Buffy Season 2 would be OFF LIMITS until I’d made a decision and could handle my shit.
An example?
I stopped CPR, after all it's no use
The spirit was gone, we would never come to
And I'm pissed off you let me give you all that youth for free
When you listen to the track, you’ll hear Taylor’s voice break on “for free,” as though she’s about to cry, and I believe she was. It is so pure and raw.
This is the first time she’s had a long-term serious relationship, which means this is the deepest romantic loss she’s experienced, and we can just feel it in this gorgeous song that also sound like it should be sung in a frikkin’ cathedral. I’m obsessed.
Trivia: The lover she’s leaving in London is the aforementioned Joe Alwyn, an actor best known for, well, dating Taylor Swift, but apparently second best known for an Ang Lee movie called Billie Lynn’s Long Half-Time Walk. Most of their relationship was spent during the time she was hiding from the public, post-Kanye-and-Kim humiliation, and then during COVID. Isolation seemed to suit them, and there were rumors that they even got married, or had an unofficial commitment ceremony, during lockdown. It is speculated that as their relationship became less isolated, both because the world opened up and because a more healed Taylor naturally wants a more public life than she had been living while in active trauma, their dynamic wasn’t as compatible.
It also seemed that Taylor very much wanted marriage and family with him. So when she says the line “all that youth for free,” it very much bears the weight of the idea that she might have given him years she could’ve been having kids, thinking he’d reciprocate eventually with commitment and children. But when the bill came due, it is speculated, he wasn’t ready or able to pay.
5. Cruel Summer
I keep wanting to kick Cruel Summer off the list because those synths, those lyrics - it’s not quite my favorite enough. But then I remember that bridge and I bring it back every time.
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I mean, do you hear the joy of that crowd?
Trivia: This song is said to be about the beginning of her relationship with Joe, when they were supposedly keeping it casual and he was still seeing other people and she was trying to play it cool like she didn’t care, but she was starting to have real feelings, and she finally got wasted and blurted out the truth, afraid it would end everything if he knew, but instead he reciprocated and they dated for almost a decade. Which is SO RELATABLE except for the “he reciprocated and they dated for almost a decade” part. But who hasn’t spent a whole summer pretending not to be in love with someone so they can keep having fun with them as long as possible? No one? Just me and Taylor? Ok fine. You can skip this song then. Unless of course you like a catchy bridge.
6. Shake It Off
Okay, so honestly, I’m kind of sick of this song now, but I’m including it because it was probably my first favorite Taylor Swift song, and because the music video is just an unmitigated delight, start to finish. Plus, the video is a perfect example of what I was talking about in my last post, about Taylor being sort of relatably dorky and awkward. And yes I know this can kind of fall into an eye-rolly Zoey Deschanel-style “adorkable” try-hard territory, but honestly, I find that trying hard relatable and charming too, and so, apparently, do, like, one bazillion people.
7. Look What You Made Me Do
This song, particularly the chorus, is kind of weird. I remember when she debuted the video at the 2017 VMAs. I thought the video was interesting, gorgeous, and funny (the concept is that her recent traumas has killed who she used to be, and there’s a scene at the end that sends up past versions of herself - mostly recognizable from past videos and performances and also that famous Taylor/Kanye VMAs moment - and all the criticisms the public has levied against her, and probably has levied against herself). But I wasn’t sure this was a song I liked, or that I would actually listen to.
Turns out I was wrong. That weird ass chorus, with its weird ass rhythm, is one of those Taylor creations that is so bad it’s… good? Maybe even was good all along? Plus there’s a certain vengeful driving rhythm to this song that has a catchy energy that kind of sneaks up on you. In spite of myself, this is one of my kitchen counter dance songs.
It has also, in the process of writing this, made me wonder what exactly “you” have made her do. And so I looked it up. (You’re welcome!)
Here are theories about what she was made to do: Defend herself in court when someone who sexually assaulted her sued her for defamation. Defend herself against Kim and Kanye’s character assassination campaign. Go into hiding. Literally leave the country and not leave her house for an entire year. Keep her relationship (uncharacteristically) secret. Do (uncharacteristically) no press for Reputation. Change her sound. Make this album. Abandon whatever album she was working on before it became necessary to work out her feelings on this one. Take a stand. Advocate for herself. Leave her people-pleasing ways behind and grow (and/or become harder/more jaded/more traumatized) as a person.
Oh also, for the record, I like the Eras Tour version the best (in the vid below) because it highlights the punk/rock elements of the song by leaning more heavily on her rock/metal guitarist. Part of what I like about Reputation in general, is it has a darker, angrier, more rock vibe. This album (and song) has attitude and swagger. (Also worth noting: the primary image for this album and song is the snake, because that’s the emoji that people kept using on social media during the #TaylorSwiftIsOver campaign to denote that she was lying about the Kim/Kanye situation. You’ll notice that not only is she wearing a snake-themed outfit, but ‘80s kids with an eagle eye may pick up that she is also quite literally doing the dance move called “the snake” lol. Oh Taylor. You so cheeky.)
Trivia: Apparently that weird ass chorus is an interpolation of Right Said Fred’s “I’m Too Sexy,” so much so that Taylor credited RSF in the liner notes. All I have to say is: SO MUCH LOL. Oh also, there are about a bazillion of Tay’s signature easter eggs in this video. You can read about them under “Analysis” here, though there are of course a thousand more theories on reddit.
8. Death By A Thousand Cuts
Okay so this thing has been happening to me since I started listening to Taylor Swift in like 2014 where sometimes I wake up with one of her songs in my head and it just plays over and over and over until I satisfy the urge by playing the song, and then sometimes even playing the song doesn’t do it and I have to actually listen to that song over and over and over until whatever synapse is glitching has unglitched, or whatever hormone needs releasing has been released, or whatever core memory needs unlocking has been unlocked, and I can never every predict what song it’s going to be. Last one was “Down Bad.” And lately?
It’s “Death By A Thousand Cuts.”
Over and over in my head, I hear “Saying goodbye is a death by a thousand cuts, flashbacks waking me up” in an even, balanced cadence, and then a beat, and then “I get drunk, but it's not enough” and then the brilliance is there is no breath or beat it becomes a run-on sentence rhythm because that’s how fast the painful realization hits her every morning “ ‘cause the morning comes and you're not my baby” and something about the way she says “not my baby” is so profoundly catchy that I simultaneously hear all of this in my head over and over but also superimposed I just hear “not my baby” over and over ALSO and then I play the song and immediately after that “not my baby” our Taylor drops that incredible pop drum machine beat with the heart-beat double bass tap and then those tinkling bell-like synths (I think) and then actual bells and well that’s just the beginning and so that is my essay on why this song goes on the list today thank you for listening.
Trivia: Apparently Taylor was inspired to write this song while watching the (exceedingly mediocre but kinda charming I guess?) Gina Rodriguez rom-com Someone Great, written by Jennifer Kaytin Robinson, who apparently was inspired to write this movie while listening to Taylor Swift’s album 1989, particularly the song “Clean” (which fully disclosure I had to look up because I didn’t even remember that’s a song, but I checked and don’t worry, it’s good) and that’s just a pop-culture ouroboros that you couldn’t orchestrate if you tried.
9. … Ready For It?
So this one might just be about fun and I’m fine with that. When this song comes on, it just makes me want to move, even if what that means for my disabled ass these days is tiny hand movements at the kitchen sink while my organic oatmeal is in the microwave.
There are five distinct modes of this song: 1. the strut around badass part, 2 .the intensifying sexier part (in fact, this might be her sexiest song), 3. the dreamy romantic sing-a-long part (which makes the return to the strut around part super fun), 4. the don’t-fuck-with-me “let the games begin” part, and 5. the vocal improv part with the super fun high notes and harmonies (all of which overlap, at some point or another), and all of those parts are fun.
I mean, look at this choreo from the Eras Tour and tell me you don’t want to that “games begin” football move at the end with them. TELL ME YOU DON’T.
Plus it’s hard to separate this song from the video, and the general vibe and imagery of this album. If 1989 was her first real pop album, Reputation was her first real foray into electronic and even industrial sounds, and a darker, more confrontational attitude that was funAF, and a lot more appealing, for me anyway, than the aw shucks country girl of days past.
A final thought: that throat-clear at the beginning of this song is just… chef’s kiss. These are the little delights, the little moments of humor and attitude, that really define Taylor’s music. Where someone like Beyoncé takes herself very seriously, Taylor does the exact opposite - and that’s what we love about both of them. (But, honestly, why I love Tay more. Sorry, Bey.)
Actually a final final thought: Billionaires shouldn’t exist. But given that they do, I kinda like that two of them are women who got there for their extreme talent, and especially that in the case of Taylor, every penny of it is related to her music and her art, not celebrity status and access parlayed into tangential businesses like make-up or clothing or even a streaming service. She is also notoriously generous with her money - she pays her dancers and staff well, often gives bonuses, donates huge amounts to charities in every town where she performs. Though I would like to see her do even more, given that no billionaire can ever spend all their money in a lifetime and she could probably single-handedly, say, solve the homelessness crisis in some mid-sized city, I appreciate what she does do, when so many of them don’t do shit (or, you know, even worse, do active harm). And before you start in on the conspiracy that this is all part of her manipulating us to think of her as kind and polite and generous when in actuality she is a cold, calculating shrew, I challenge you to listen to her song Marjorie, about the values her late grandmother instilled in her, or to watch the recent vid of her backstage at a Chief’s games, correcting her security guards to say “please” when they give people direction. I honestly think Taylor is just a kind and thoughtful person (though there is also an argument to be made that she has to work twice as hard to prove that, because of #misogyny and #patriarchy).
10. The Smallest Man Who Ever Lived
I’m kinda bummed The Tortured Poets Department didn’t come out about 10 years ago, because I really could have used some of this energy when I was going through my last devastating break-up, though honestly that’s still the heartstring this song (and this album) plucks, and boy does it do a deliciously recreationally painful good job.
There’s a quality in this song that reminds me of listening to All By Myself, or Nilsson’s Without You, or maybe a ballad cover of You Oughtta Know, though those songs sound very different. But there’s a drama. An agony. Anger and unbearable pain.
Like them, this song is visceral. Like them, you can hear she’s having genuine emotion as she’s recording. If she’s not throwing herself on the floor in despair while singing this song, it’s only because that would make it very hard to reach the microphone.
For a sense of how I first started to appreciate this song, it looked a little like this video:
It should be noted that after Taylor recorded TTPD, she trademarked the phrase “Female Rage: The Musical,” which became the name of the new TTPD section she added to the show, and boy is it glorious. This song is only one part of it, and not even the best part. You’ll see more TTPD songs on my list. This is just the one I happened to be listening to tonight while doing my weird medical machine ritual, and finding myself wanting to collapse and die from heartbreak even though I haven’t even kissed anyone since 2017. But that’s THE POWER OF MUSIC.
Btw, check out this video from Dublin. I showed it to my mom, pointing out how wild it is that you can hear the entire crowd sing along with Taylor even from the other side of this river, and how satisfying it must be to have 70,000 people sing “Good Riddance” to your shitty ex along with you. My mom said “I wish someone would write a song like that about your ex,” and, well, that’s how you know we both have prominent Scorpio placements. Also, check out the caption on this video: “Who hurt them…” LOL.
And that, my dear friends, brings us to the end of Part 1. Stay tuned for Part 2…
Til then.. xoxo
Just…perfection. 👌
The post-election perk-up I didn't think I could get...thank you!