TechCrunch staff asks: What’s really the best Taylor Swift song?

While TechCrunch is a Very Serious Publication, at times we wind up a little off-topic in our internal conversations. We talk video games. We talk bad reality television. We riff on sports and pets and our families. And we talk about music.

Naturally, with as diverse a group as our team, viewpoints vary. But one notable point of commonality is Taylor Swift. Yes, your tech news is frequently prepared by a dyed-in-the-wool Swiftie. Perhaps even more often than not.

This raises an important question: Which Taylor tune is really the best? After realizing how many of us scribblers had an opinion on the matter, we decided to make our case in a public manner. What follows is a series of arguments – written in three-views style, albeit with more players – about which Taylor Swift song truly sits above the rest.

We welcome your public comment, of course, but note in advance that if you don’t agree with at least one of us, we all think that you are flat-out wrong.

Alex Wilhelm: Wildest Dreams

I view my Taylor Swift fandom as indicative of her universality. I am presently counting down for new records from In Flames, Lorna Shore, and other heavy metal bands that very few readers of this article are going to put on when they drop. That’s fine; musical tastes are personal. And yet here we are, sharing our passion for Swift’s singing and songwriting, despite our different musical preferences more generally.

The universality point is not merely one about her musical type being welcome by folks of many musical bents, however. It goes deeper.

Listening to Taylor’s discography is to watch her grow up. And as – per a quick peruse of her Wikipedia page – she and I are within a half-year of age, her transition from youth to young adult to 30-something has also been my own; her catalog essentially tracks my own maturity arc. But as we can see from her older and younger fans, the same life progression resonates with folks even apart from the age that she and I share.

Why is that? Lyrics, in essence. Taylor’s tunes kick off somewhere in the realm of youthful insecurity (“Fifteen,” etc.), progress into an era of confidence (“Shake It Off”), through a period of experimentation and anger (“Look What You Made Me Do”), and finally wind up in the pandemic era, when she managed to make cottage-core cool (“Cardigan,” “‘Tis the Damn Season”), writing to us from a place of emotional resilience, now past her more turbulent 20s.

Yep, that hits home. Inside those albums are a host of standout tunes, some of which I mentioned above. Which is my favorite? As an imported Rhode Islander with some claim to Midwest roots, you might imagine that “The Last Great American Dynasty” would be my go-to. It’s a killer tune, but not my all-time fave.

No, the best Taylor Swift song is “Wildest Dreams.” Why? It is the platonic ideal of Taylor’s patented mix of melancholy, melody, and optimism; it blends her eras, her growing up, really, into a single, perfect, song. By bringing so much of what Taylor does well into a package of less than four minutes, it’s the correct song to cite as her best.

Thanks, Tay. Keep writing.

Dominic-Madori Davis: State of Grace (Taylor’s Version)

If I remember correctly, one of the first vinyls I ever bought was Taylor Swift’s “Red.” I was in high school, and something about that album encapsulated the anger, confusion, and wistful hopefulness I felt at the time. I never considered myself a Swiftie growing up, but looking back, much of her music laid the soundtrack for my life.

Last year, for some reason, I listened to “Seven” more than 350 times as we all re-entered life after pandemic lockdowns; the newness yet the familiarity of life left me longing for something only that tune could touch.

There was “August,” the salt air, and the “Long Pond Sessions.” I think of the masterful lyrics of “This Love” from “1989” or even “New Year’s Eve” from “Reputation.” The album “Lover” was quite nice, and who hasn’t screamed the chorus of “Cruel Summer” at least once in their heads, in their cars, with their friends? “Evermore” can have a shoutout here; I remember “Cowboy Like Me” was the first song I dramatically put on when I realized my crush had a girlfriend, and “Long Story Short” followed when they broke up.

Perhaps mostly, I recall those early Taylor days with me spinning around in my bedroom listening to “Enchanted” or looking out the window as my mother drove me home with “The Best Day” playing softly in the background. I remember when I first heard “Tear Drops on My Guitar” on the radio. I was a kid in the backseat of my mom’s car.

I don’t think anyone knew at the time what that hit single would lead to, and each time Taylor re-releases her old albums, I feel like that child once again in the backseat, even though I’m an adult, somewhere in New York City, finally understanding what those emotions all mean.

Though, no matter what Taylor does, I am always drawn back to “Red.” I love “The Lucky One,” and it reminds me of when I went to school in Los Angeles and had my first encounter with Hollywood. I was new to town, in the Angel City, around those seeking fortune and fame. I once wrote a college essay about “Treacherous,” about those moments of intense passion and often unrequited love. Even when I turned 22, nearly a decade after the album was released, the first song I put on at midnight as — well, I think it’s obvious at this point.

What I’m trying to say is that it’s pretty hard to choose what Taylor’s best song is. It for sure exists on “Red,” as that album holds some of her best lyrics; scathing, raw, forgiving, and sanguine. I mean, have you ever called someone up again just to break them like a promise?

Today, I’m much older than when that album first came out. I’m not sure what her best work is, but I can say this for sure: The acoustic version of “State of Grace” matched with the stadium rendition hits the tense two-sided coin that is the uncertain lust of one’s 20s. That’s where I am right now — so at least for today, I’ll have to go with that one.

Amanda Silberling: All Too Well (Taylor’s Version)

I wouldn’t call myself a Swiftie, mostly because when I was most primed for Taylor Swift fandom – my teenage years – I was suffering from an undiagnosed case of internalized misogyny, trying to make everyone think I was cool because I listened to the Velvet Underground. Now, as an adult, basically all I know about Taylor Swift is that she’s obsessed with the number 13, her fans should maybe stop harassing journalists for writing an 8/10 album review, and that she gets way too much flack for being a woman who dates people and writes about it.

But something I am unequivocally obsessed with is whatever the internet is talking about on any given day, so every time a new (Taylor’s Version) dropped, I wanted to know what the discourse was about. And the Swiftie discourse was never louder than the day that the 10-minute version of “All Too Well” dropped. Ten minutes? What is this, some progressive metal song that Alex would listen to?

But that song deserves to be 10 minutes long, and I’m a terminally online millennial with a social media addiction, so if I can be entertained by an artist I’m not obsessed with for 10 minutes, you know she’s good.

I didn’t even know that Taylor Swift had dated Jake Gyllenhaal until that song dropped (chill, she’s not complaining about her 10-years-ago ex, she’s re-recording music that Scooter Braun is holding hostage, which is really badass of her, so get over yourself). But damn. “You called me up again just to break me like a promise/so casually cruel in the name of being honest.” Fuck internalized misogyny; Taylor Swift can write. That lyric took me right back to when my high school crush told me that he wouldn’t date me because I wasn’t mentally healthy enough. To be fair, he was right – don’t worry, I’m in therapy now! – but did he have to say it like that? If “casually cruel in the name of being honest” doesn’t yank you straight back to your failed attempts at teenage romance, I envy you.

When Taylor’s version of “All Too Well” dropped, I probably tweeted something about how I never even knew the original version, but this song slapped – and then my internet friend Giovanni sent me a playlist he made called “T Swift is good, actually,” which he just always has on hand to convince people that Taylor Swift is good.

I gotta say, he did convince me.

Anita Ramaswamy: Blank Space

Much like Amanda, my own adolescence was defined by music that was a far cry from Taylor Swift’s sugary pop-country crossover tunes. I found solace in sitting in the back row of my class, blasting “I’m Not Okay” by My Chemical Romance into my skull through a single earbud because it was uncool to use both simultaneously. Swift, meanwhile, was a conventionally attractive blonde woman who didn’t make me feel particularly seen as a gangly, outspoken Indian high schooler surrounded by, well, pageant queens (I grew up in Scottsdale, Arizona. Leave me alone).

But there’s a distinct moment I remember Swift really seeing me, piercing through my soul, laying it bare. It’s when I saw her in the “Blank Space” music video, destroying a classic car with a golf club outside a luxurious mansion. This was the moment that marked, in my eyes, Swift’s transformation from a perfect pop princess into a real person, with anger and raw emotion and plenty of flaws.

The best part is that Swift was doing it all on her own terms and refusing to be put in a box: “Keep you second-guessing like, oh my god, who is she?” After years of having her narrative defined by what other people said about her, here Swift was, getting loud and wild and signaling to the world that she was going to do what she wanted to do, regardless of what people thought. Demanding to be seen as she is, and in the process, seeing me.

Annie Saunders: They’re all the best and if you wanna fight about it we meet in the park at dawn

As a 30-something woman who recently exited a 10-year marriage, it goes without saying I’ve been listening to a ton of Taylor Swift. Nonstop Taylor Swift. An absolute wall of Taylor Swift.

So sure, “We Are Never Ever Getting Back Together” and “I Knew You Were Trouble” were totally contenders here. They’re absolute fucking bops that have been on repeat for the last year-plus. My 4-year-old son knows all the words to at least a dozen Taylor Swift songs; at the moment, he sings “Wildest Dreams” till he falls asleep every night, adding weight to Alex’s argument.

I eschewed Swift for a good chunk of my late 20s and early 30s (see Amanda’s point re: internalized misogyny), and it’s only now — with the context of the pandemic, 15 years in the workforce, a divorce, a child, Trump, #metoo — that I recognize what a confidence-booster she’s been not just for me, but for lots and lots of women around my age.

This is hard! She has so many songs that validate my emotions! I mean, ever take a hard listen to “Mad Woman” and recall all the times you’ve been gaslit? What about “The Man”? “I’m so sick of running as fast as I can, wondering if I’d get there quicker if I was a man.” It’s a must-listen in advance of a salary negotiation. I sometimes feel like she wrote “Long Story Short” just for me.

I can’t do it; I can’t choose. I celebrate her entire oeuvre. It’s all the best. And if you don’t think so, I’m up for fighting about it … because I listen to so much Taylor Swift.