Fearless – There’s a Rob Sheffield bit I remember reading where he describes hearing this song for the first time (literally through the phone because they were desperately trying not to leak it). He says something along the lines of “Oh shit. She wrote the perfect pop record,” and honestly, that’s the easiest way to put it. It’s difficult to think of a song that better captures how we collectively imagine young love – naive, enormous, fearlesss – when a long drive and a little rain somehow feels more magical than an old fairytale. [9]
Fifteen – “It’s your freshman year … Hoping one of those senior boys / Will wink at you and say, ‘you know I haven’t seen you around before,’” is a line that made me wince when I was 15 but makes me laugh at 21. Because Mady Abigail (my best friend who I met when I sat next to her our first day) did give her everything to a boy who changed his mind. And goddammit, we both cried. So, slightly problematic age gaps aside, I can’t knock this song for being cliche or preachy when my own life somehow managed to imitate the art to an eerie degree. [7]
Love Story – When I was nine, my older cousin picked up a copy of Fearless from a CD store down the block which illegally imported music across the border from Nepal. I heard Love Story for the first time in my uncle’s Maruti Suzuki as it routinely stalled down the streets of Northeast India where cows marched along the spots a bike lane was supposed to be. Except that wasn’t really where I was at that moment. In a literal sense, sure. But when this song plays, I can’t actually be anywhere except its pages. The 2008 version of “Love Story”is a starry-eyed teenage girl daydreaming her life as a movie; the 2021 version of “Love Story”is a fully-grown woman telling us that what she got was even better (this time with the budget for a full orchestra). There’s a bittersweet element in picking “Love Story”as the starting point for what will be a full-blown retrospective on Taylor’s career – a time before “Dear John”, “All Too Well”, “my tears ricochet”. The song today can serve to preserve a sense of youth, when claiming a teenage crush could rewrite the course of a Shakespearean tragedy felt appropriate and was powerful enough to capture the imagination of a generation. Lucky number thirteen years have passed, and my relationship with Taylor Swift endures. [10]
Hey Stephen – “Hey Stephen” encapsulates most of what John Mayer wishes he could do. The song is a charming little number with an easy-going humming solo to boot, never overstaying its welcome or coming off as too pompous and constipated. [7]
White Horse – In the pantheon of Taylor’s breakup anthems and track 5’s, “White Horse” is a meek contender. Not as grand as the name suggests, nor as devastating as one might expect based on the way she’s described falling in love. This is the result of a breakup where it seems she fell in love with the idea of love rather than the guy himself, so the track fails to be emotionally compelling. It was never really about him to begin with. In hindsight, this song reads more like the rough draft of a tale burning Red. Because when it is about the guy, that’s a whole different ball game. [6]
You Belong With Me – Is there any explanation for why “Treat You Better” makes me want to vomit in my mouth but “You Belong With Me” has me in wire-rimmed glasses, dyed red hair in galaxy buns, reblogging Ramona Flowers gif comps that pop up on my dash? Do I have a bias against men? Canadians? Is it just the way Mendes screeches “beh-TUH then he cen”? That last point is possibly half the reason. The full explanation is that the sheer specificity with which Taylor describes her situation as a female incel makes me more empathetic. While Shawn is operating off vibes alone (“I know he’s just not right for you.” Do you actually know that Shawn? How could you possibly know that?) Taylor goes full-send with the judgement and calls his girlfriend an airhead Barbie with shit taste in music. It’s impressive how convincing Taylor sounds when she literally was the “other girl” everyone was complaining about on tumblr. [8]
Breathe – The re-recorded instrumental track for this song adds some depth to the original. You can really sink into the string arrangement. This song is also notable as the first instance of an amusing habit Taylor has for giving her female “featured artists” just the backing vocals on her songs (“You All Over Me”, “no body no crime”, “Soon You’ll Get Better”). [7]
Tell Me Why – The violin arpeggio motif that runs through this track brings momentum to what would have otherwise been a forgettable number. Taylor doesn’t provide much explanation for her bitterness towards the subject aside from being “sick and tired of your attitude” and “feeling like I don’t know you”. Overall, it’s just an underwritten song. [5]
You’re Not Sorry – A country-pop power ballad that’s giving…. Apologize? By OneRepublic? Well, if anything, “You’re Not Sorry” fails on similar fronts, lacking the vocal performance or emotional complexity of future releases like “exile” or “Back to December”. With that said, I would be lying if I didn’t admit the chorus of this song very quickly attached itself to my hippocampus. [6]
**sidenote from the future: so it turns out the speak now tour featured a back to december/apologize/you’re not sorry melody which i didn’t know about prior to writing this blurb. it’s very good, would recommend.
The Way I Loved You – It’s the messy stories that feel the most real, when your feelings stretch beyond the realm of logic but still make sense to whoever’s listening. “The Way I Loved You” taps into the irrational magic that can turn into frenzied infatuation. It’s a feeling that can blind you to any incompatibility if it’s too strong, or make you leave a perfect partner if it’s missing. It’s when “feeling perfectly fine” becomes the relationship’s death sentence. [8]
Forever & Always – “Forever & Always” leans too far into stock Taylor Swift-isms without any of the necessary seasoning; it’s always raining, some vague promises were broken, it all happened so quickly. At this point in her career, Taylor is better at writing about falling in love than out of it. [5]
The Best Day – I would not be upset if Taylor never wrote another “middle school nostalgia” song ala “Never Grow Up”. They’re not particularly offensive or grating, she just fails to convey the childhood wonder I think she’s going for. [5]
Change – “Change” is about overcoming hardship in Nashville and finding success despite coming from a small label, none of which I would have guessed without a Wikipedia search. I always feel like a bit of a dick when I shit on something that clearly has meaning to the artist, but “Change” reads like an adult contemporary self-empowerment anthem that would play in the trailer for this summer’s kids with cancer romantic drama; this is my “Fight Song”. A curious choice for a closer. [4]
