Mrs. Sędek, the Swiftie - Taylor Swift Playlist for Steele's Friend! (Patreon)

Hey everyone! A few weeks ago I mentioned on the podcast that my friend who knows nothing of Taylor outside of "Shake it Off" asked me to make her a Taylor Swift playlist that would provide a brief rundown of her best music and career. Aaaand, it being me... this rundown ended up being anything but brief. A lot of you mentioned that you wanted to see the playlist and read what I wrote for her. So here it is! Hope you enjoy!Mrs. Sędek, the Swiftie

Okay, Eileen. First thing I need you to do is drop everything you learned about music post-middle school and get yourself into the mindset of a 14 year-old, emotional, lovetorn girl. I’m talking the most brokenhearted teenager you’ve ever met in your life. I’m talking fresh-off-the-breakup-with-her-freshman-year-boyfriend-Eileen. You want impressive breath support or complex vocal tone? Honey, you’re not gonna get it. But what you WILL get is a loyal bestie to laugh with you and cry with you and relate to you through her great stories and fabulous musical hooks. And even if none of this suits your fancy, I hope this novel I’ve written will at least give you some insight into the trajectory of her career and the evolution of her writing. ENJOY! 

Taylor Swift (2006): Her first album is pretty honkey-tonk and very easy to swallow by an audience that’s just looking for its 16-year-old country darlings to be sweet and harmless. I wouldn’t call it a bad album by any means, especially considering her age and the fact that it’s a debut album. But it’s not one I ever revisit outside of a couple cute songs. Still, I wanted to include one song from it so you have the full scope of her discography. 

Our Song - Of all the earlier super country stuff from the first album, this is my fave. I think you get a really good sense of her potential as a songwriter.

Fearless (2008): Her first Grammy for Album of the year. Technically speaking, song-for-song, this is absolutely her most consistent album. While albums like Speak Now and Red have much higher highs (and much lower lows), there are virtually no skips on Fearless. Just great, well-structured tracks, which is impressive when you consider many 17-year-olds can barely even structure a simple sentence. The songs don’t go wildly deep lyric-wise, but that adds to the relatability she had with her fans. She has such a clear and specific way of putting things. Even though she indulges in the “teenager with fairy tale fantasy” a lot on this album, she still doesn’t seem to pander to the mindset. You can tell it’s just kind of the stuff she was into, so it feels genuine and not like she’s talking down to the demographic.  

Fifteen - I think this really represents her ability to tell a story and appeal to the teen girl market at the time. It’s a nice mellow and thoughtful diddy. And the fact that she’s a 17-year-old proclaiming, “I know so much more now than I did two whole years ago!” without the song veering into insufferable is a miracle. I also wanted to include it because I’m now picturing you as Taylor and me as her redheaded best friend Abigail, and we’re both in your bedroom crying about boys.        

Love Story - I’d be surprised if you’ve never heard this song. It’s a classic. And, yes, very frilly-froo-froo-fairy-tale… but SUCH well-done frilly-froo-froo-fairy-tale! Flawless. No notes. I’m a 35-year-old man who squeals whenever she sings, “I talked to your dad, go pick out a white dress!” I can’t wait to see your daughter’s rendition in seven years.

You Belong With Me - You told me you know this song already, but it feels wrong to not include it. And I just need to remind you of the perfection that is the pre-chorus: “She wears short skirts, I wear t-shirts, she’s cheer captain, and I’m on the bleachers.” A hook for the AGES.

Forever & Always - I think this song just represents the rest of the songs on this album pretty well. Well-done, personal but not too deep in the emotional trenches, pop country. It also has a really good piano version on the deluxe album.

Speak Now (2010): This is my personal favorite Taylor album. I think it perfectly encapsulates her strengths as an artist with the storytelling aspect and specificity of her lyrics. She starts to move away from the, “I’m just like you!” to “I’m a star now, so my problems are bigger and grander and more detailed.” She famously wrote this album without any co-writers (minus the final track) after a lot of the general public doubted she did any writing on Fearless. It was her first “lemme prove the haters wrong” moment. She happily indulges in the drama of so many of these songs, so it really feels like the stakes are high… absurdly high at points. But you just have to go with it and pretend like you’re 19 and indulge with her!! Just do it!! It feels good!!   

Mine - This was the first single. It feels the most like it could be on Fearless but, again, just BIGGER with more lush production.

Speak Now - An adorable, sugary teen fantasy power anthem that could only be written by Taylor! You get SUCH a strong story that’s funny and charming and relatable and makes me want to crash every wedding.

Dear John - Okay, this is where shit starts to get real, Eileen. Taylor does many things well. But this is where we discovered what Taylor does BEST: An Epic Shame-Jam. Here we have the dragging of John Mayer. It’s the first (and only) time she says an ex’s actual name in a song. Worth every second.

Mean - Here she is dragging everyone who says they don’t love her voice. And okay, it's not like she's doing much vocally here to disprove their point, but dammit, dammit, dammit, she’s proving that she can write a SONG!! 

Enchanted - The fact that she can take something as simple as meeting a cute guy and wondering if he’s single AND TURN IT INTO A SIX MINUTE OPUS… Euphoric and devastating and perfect. I was a little whatever about this one for the longest time, and now it’s risen in the ranks as one of my favorite songs from her. Another fun fact, the album was originally going to be called “Enchanted,” but the record label thought the public would be annoyed by yet another allusion to fairy tales.

Last Kiss - Another long, slowww shame jam. It feels like a funeral march. But, baby, throw that dirt on me cuz I’m in that coffin loving every slow-ass second. I love the specificity with the lyrics. She’s not just giving you a setting of a scene. She’s like, “It was JULY 9TH. A TUESDAY.” We love a girl who can ruin a man by remembering all the details. And “So I’ll watch your life in pictures like I used to watch you sleep, and I’ll feel you forget me like I used to feel you breathe” remains my absolute favorite Taylor lyric.

Red (2012): This is when it became clear that Taylor was veering away from country and was wanting to transition into pop. She finally dropped her fake southern accent (girl, you’re from Pennsylvania) and incorporated more modern production in a number of songs. And the hooks started to become a lot more simple and pop-y (*see “We Are Never Ever Getting Back Together”). Like Speak Now, the highs on this album are astronomically high, career-defining moments. However, this was the first album (of a few) that she made a little too long and included some forgettable stuff. The first two-thirds of this album are fucking amazing, and then it falls off for the last third. But, still, these tracks are among her best. 

State of Grace - The album opener that lets us know we’re about to start blending pop into the country world a little more. There’s also a greatttt acoustic version of this song on the deluxe version of this album.

I Knew You Were Trouble - You’ve absolutely heard this one. I feel like it’s fallen out of the public eye as time has gone by, but it was everywhere back in 2012/2013.

All Too Well - ALERT!! ALERT!! This is Taylor’s best song! Point blank! Period! If you listen to nothing else, listen to this. The shame jam of all shame jams. The song that forced Maggie Gyllenhaal to publicly proclaim, “I swear I don’t have Taylor’s scarf!”

22 - Some people hate this song because it’s annoying. Some people love this song because it’s annoying. I love this song because I’m annoying.

We Are Never Ever Getting Back Together - First single off the album and her first #1 on the Billboard Hot 100. You’ve heard it before. A pop anthem.

Begin Again - Some people find this song “meh,” but I’ve always had a soft spot for it. So I’m putting it on here because this is my list, dammit, and I’ll do what I want.

All Too Well (10 Minute Version) - Released in 2021 as a “vault track” when she released Red (Taylor’s Version). She basically just expands upon an already perfect masterpiece to make it an even longer, even more perfect masterpiece. She claims this is what she originally wrote back in 2012 before she had to whittle it down… but the fact that all the new melodic moments sound like what she was writing for folklore/evermore eras in 2020 makes me not believe her. But whatever, she can lie all she wants because it’s “All Too Well.” It was also when this version of the song came out that twenty-something-year-old women (who were fifteen-year-old girls in 2012) finally realized, “Oh… maybe Taylor’s ‘red scarf’ was a metaphor for her virginity… Sorry to bother you, Maggie!”

1989 (2014): A major landmark in her career because it was her official transition into pop. She teamed up with huge pop names like Max Martin and Jack Antonoff to put together an incredibly sonically cohesive album that brought 80’s synth back to the forefront. While I can appreciate a lot of what this album did and can acknowledge that two songs on it are legit some of the best pop songs in history, it kind of lacks her signature lyrical specificity and storytelling. BUT it’s an incredibly polished album, musically, that was wildly successful (it’s the album that includes “Shake it Off”), and it won her her second Grammy for Album of the Year.   

Blank Space - You’ve heard this without a doubt. It’s one of the best pop songs of the 2010s. A hilarious and self-aware earworm that pokes fun at the reputation she garnered for her dating habits. “I can make the bad guys good for a weekend” is another one of my favorite lyrics from her - creating her own version of the age-old trope of making “good girls go bad” that male rock stars love to use in their songs.

Out of the Woods - A pop song that is so simple yet gives us passion, joy, fear, HEFT, everythingggg. Her co-writer and producer Jack Antonoff perfected his signature sound here. A legitimate pop masterpiece. 

Clean - I think the ballads on 1989 are generally just “good,” but this is the ballad on here I would call “great.” Co-written with Imogen Heap, it’s a great blend of both their skills put together.

Reputation (2017): Reputation has seven-ish really strong songs on it. Unfortunately, the album is sixteen tracks. This was her, “I’m gonna stick it to the haters!!” album, so she went into this era guns blazing. 

CONTEXT: This was off the heels of the scandal with Kim Kardashian/Kanye… Not sure if you knew/remember the details, but basically Kanye put out a song with a lyric, “I feel like me and Taylor might still have sex. Why? I made that bitch famous!” (referring to when he interrupted her VMA acceptance speech in 2009). The song came out a few days before the 2016 Grammys ceremony, and Taylor was silent about the lyric up until that night. She finally addressed it on stage while accepting her second Album of the Year Award for 1989: “And as the first woman to win album of the year at the Grammy's twice, I want to say to all the young women out there, there are going to be people along the way who will try to undercut your success or take credit for your accomplishments or your fame. But if you just focus on the work and you don't let those people sidetrack you, someday when you get where you're going, you will know it was you and the people who love you who put you there, and that will be the greatest feeling in the world.” A brilliant PR move.

Everyone seemed to be on her side of this beef after this… until a few months later… on NATIONAL SNAKE DAY… when Kim Kardashian released a video of Kanye on speakerphone with Taylor before his album came out. The video shows him telling Taylor that he’s planning on including a lyric saying he “made her famous,” and Taylor is on speakerphone saying, “Oh, that’s fine. I appreciate you letting me know!” So essentially Taylor was “caught” originally being cool with the lyric before then taking offense to it publicly on the Grammys stage. Taylor quickly responded, saying that Kanye never mentioned he’d be referring to her as “that bitch” in the lyrics, so that’s what she was claiming to be upset about. More video footage was also released of the full phone call confirming he never warns her about the “bitch” part of the line. But after all this, Taylor still got a lot of bad press. And it really fueled the already increasing narrative of her being manipulative and great at capitalizing off of “playing the victim.” 

So of COURSE Taylor decided to play into her own reputation and capitalize off of this scandal (and her persona as a whole) for this era. Everything was darker and sexier. There were a ton of snakes in the imagery of all the marketing and videos of this album (to tie it back to Kim calling her a snake). She really committed to it. My problem with this era tho is that Taylor is not dark or edgy. She’s a sweet girl from a wealthy upbringing who loves cats and singing about fairy tale fantasies. It kinda felt like if you or I decided to suddenly be “bad” in high school. It’s just not in our blood. So despite it being a more personal album than 1989, it felt a bit like she was putting on a weird costume, sonically. It’s very abrasive and bizarre and messy in moments. But there ARE some songs that work!

I can’t believe I wrote this much about an album I don’t even think is great. DAMMIT! Taylor is just so good at getting people to talk about her, even if she isn’t at her best!! A MASTERMIND (great song coming at you a little later). 

..Ready For It? - A noisy opener to a noisy album. While the production has the same grating quality that pervades almost the whole album, I still really like this song! I think the lyrics are fun! And even though the sound isn’t totally HER, I still think it works well as a pop song. 

Delicate - One of the few times on this album she lets us breathe and gives us something light and pleasant. Also, I’m a sucker for a vocoder.

Look What You Made Me Do - This song is dreadful. This song is a blast. This song is a disaster. This song is a work of art. It was the first single - not because it’s great, but because she knew people would talk about it. So you kind of just have to be amused by how off the rails and representative of the era it is.

King of My Heart - UNDERRATED EUPHORIC GEM OF A SONG!!!!!

New Year’s Day - The last song on the album and the moment where you’re finally like, “Ohhhh yes… THERE she is. THERE’S that girl who loves sitting there at the piano and writing a sensitive, personal tune.”

Lover (2019): I WILL DEFEND THIS ALBUM FOREVER! Not because it’s perfect. It’s too long and has some clunkers on it. But because it’s her pop album that feels the most authentically HER. 1989 was sleek and cool but lacked a bit of the personal connection. Reputation felt more personal but sounded like screws thrown in a blender. But Lover was her pop album that I feel finally successfully combined her skills with her personal aesthetic. All the snake imagery from the Reputation era was replaced with butterflies and pastels and cotton candy clouds. She was also fresh into her relationship with Joe Alwyn, which would end up being her longest relationship yet. So this is absolutely her happiest album. Problem with this era, though, was some of the single choices were very bad. Then the era was cut short by the pandemic. But the good songs on this album are a joy. 

Cruel Summer - The more romantic sister song to “Out of the Woods.” You might have heard this song more recently than in 2019. That’s because it’s currently a hit. It was (INSANELY) never picked to be a single at the time. The bridgeeeeee! Because she knows how much her fans love this song (and because she’s smart and knows to release whatever she can between album cycles so she can stay on the charts), she JUST released this song as a single a few months ago despite it being over 4 years old. It hit #1 and still sits in the Billboard Top 10 as we speak. It made all the fans happy because this song deserves to be remembered as one of her bigger hits.

Cornelia Street - My heart. I think this song perfectly represents the essence of this album. I loveeee.

Death By a Thousand Cuts - A good example of her getting experimental with her songwriting without going completely off the rails. I love it.

folklore (2020): This marks the era where the Swifties were out for my blood, because folklore is regarded by many to be her best, most mature work… and I’m not into it.

One early morning in July of 2020, Taylor finally pulled a Beyonce and announced she was dropping a surprise album called folklore. It was a project she described as a collection of “story songs” she put together with Aaron Dessner from The National, and it would be her first foray into a more alternative, indie pop, electro-folk sound. Instead of focusing on more personal experiences, the concept was to create an album inspired by “stories” she conceived over the first few months of the pandemic. Aesthetically, the album/era was beautiful. It’s a very “I like to wear flannel and wander around the woods in the rain and cut my own bangs” vibe. And some of the lyrics are really gorgeous.

Howeverrrrrr my problem with this album is I just don’t feel any stakes in the music. It’s a little too lyric-focused with not enough melody for me. I can appreciate a well-written lyric - but after a decade of really feeling her personal connection behind her more simplistic & relatable lyricism, to experience aloofness from her in her writing and vocal performance here just prevents me from becoming invested. BUT I can appreciate the work that was put into this album and can understand why it won her her third Grammy for Album of the Year. It was a big step forward in her being seen as a more “adult” (whatever that means) artist. And at least it was her stretching in a new direction that felt a little more fitting than Reputation did.

the last great american dynasty - I appreciate her thinking outside of the box story-wise for this one. I think it’s a really well-done song and interesting concept.

exile - I think this song is great. I like the simplicity and think Bon Iver gives some good heft, vocally.

my tears ricochet - This is one track on this album I feel like she has a little bit of a personal connection to, so I can appreciate it.

evermore (2020): Less than five months after surprising everyone with folklore, Taylor announced, “Guess what! I was so inspired by making folklore that I just kept writing!” Evermore was released as the “sister album” to folklore and had a very similar aesthetic and concept (story songs with a more indie flair). So upon its arrival, I braced myself for another stroll through the muddy woods… 

It’s my least favorite of her albums. So many of the songs sound like unfinished tracks that weren’t good enough to make folklore. At least folklore had the excitement of it being her first foray into alternative folk! This album just feels very unnecessary with songs that feel so unimportant. And it’s Taylor Swift! This is the girl who is known for making simple stories seem like earth-shattering events! This is the girl who writes devastating power ballads about things like Jake Gyllenhaal not showing up to her birthday party! (A bonus track on Red called “The Moment I Knew,” which I didn’t include on this playlist but is hilariously thrilling) I don’t want my Taylor music to feel like ho-hum vibey poetry book music! 

This felt like the start of Taylor releasing anything and everything she worked on. It’s smart because it’s how she’s able to stay in the public eye so easily. And she knows people just love being fed any and all content right now. I think if she took her time and combined the five best songs on folklore and four-ish best songs on evermore, she could have put those together and released one very, very good short album. But instead, we got two albums of 32 songs. It’s just… a lot!    

’tis the damn season - I like the concept of the romance you always go back to whenever you visit your hometown for the holidays.

marjorie - A song about her grandmother. This song doesn’t have the strongest melody or anything, BUT it’s the one point on this album where I feel like she has any personal connection to anything she’s singing about. I think the lyrics in the bridge are particularly beautiful.

Midnights (2022): Like folklore/evermore, Midnights came about rather suddenly when she announced it at the MTV VMAs. She was in the midst of releasing all of her re-records of her previous albums, so no one was expecting her to release a whole new album for a little while. But Taylor lovesss a release. And the Swifties loveee to receive.

Midnights is another concept album where (apparently) every track is inspired by a sleepless night at some point in her life. It’s an album I think even most Swifties would admit to being her most middle-tier work. It’s quite good! But overall, it has a “was this really needed?” sensibility to it. Thankfully, sonically, we’re finally out of the woods (see what I did there) and into a slightly groovier, dreamy-pop mode. And you can hear a lot more Lana Del Rey (a good friend of hers) influences here. I think it’s an upgrade from folklore/evermore because it feels more personal, even if the stakes feel a little low. There’s some very good stuff on here, but having it be her fourth Grammy for Album of the Year definitely had people scratching their heads. 

It could partially be because the album made SOOOOO much money. Not just because she’s the biggest pop star in the world right now, but because she incorporated a brilliant tactic with merchandise. There’s been a big resurgence in vinyl collecting from teen music fans, so Taylor released this one album with four different vinyl color options. And the back covers of each vinyl formed one quarter of a wall clock. If you bought all four, put the covers together, and then bought her special clock hand wall attachments, you could have your very own working Taylor Swift Midnights Wall Clock. So Taylor was essentially selling four albums in one to Lord knows how many people. Say what you want about the girl, but she knows how to make money. Why can’t I????

You’re On Your Own, Kid - Ugh I loveee the way this song builds as it kind of combines the bridge and the final chorus!

Mastermind - Yes you are, Ma’am. I really like how it’s a bit of a dance song but feels restrained and calculated (much like how she describes herself).

Would’ve, Could’ve, Should’ve - The closest we’ve gotten to an “epic shame jam” from Taylor in a loooong time. This is a bonus track off of the album, WHICH IS INSANE. How are you gonna put so many just “okay” songs on this album and make THIS ONE a bonus track??

The Tortured Poets Department (2024): Okay, this album hasn’t even come out yet, so there are no songs from it on your playlist. BUT…

FUN TAYLOR CONSPIRACY THEORY: Unlike the other Swifties, I don’t like diving into the bizarre conspiracy theories her fans like to make up about her. BUT. Matt Palmer and I have a theory that Joe Alwyn didn’t want Taylor writing in too much detail about their relationship. In the years they were together, Taylor released three concept albums where the topics often strayed from her current life (two “story albums” and an album about sleepless nights from her past). I don’t think it’s possibleee they had a bit of an agreement that she wouldn’t put their relationship in the spotlight for the public to discuss in the same way the public was obsessed with her previous relationships. It could also be why her last three albums feel a little… safe and distanced (?) compared to her earlier work. BUT. In early 2023. Taylor and Joe broke up. And all of us around the Taylorverse began to hold our collective breath in anticipation of what the breakup album would sound like.

Fast forward to last month at the 2024 Grammys. Taylor wins Best Pop Vocal Album and announces that her new album The Tortured Poets Department will be dropping in April. My initial response was “WTF is that title?” But THEN it was quickly revealed by psycho internet sleuths that Joe, Andrew Scott, and Paul Mescal had a WhatsApp thread they called “The Tortured Man’s Club.” So we’re all expecting this album to be a return to incredibly detailed and personal story songs. And mama, I’m ready… 

OKAY THAT’S IT. You have successfully passed Taylor 101. You should have another Swiftie make you a separate playlist just because it would be interesting to see how it compares to mine. I think one of the most interesting things about her discography is how varied her fans’ opinions are of it. Because her catalogue is so huge and goes through a big evolution, there’s no super strong consensus on what is considered her “best” or her “worst.” I imagine if you were to talk to another Swiftie about this playlist, they’d be like, “Who is this psychopath that hates evermore but loves Lover?!?!?”

But would those Swifties take the time to provide you a crash course like this? I think the hell not. Therefore, my playlist reigns supreme.