Taylor Swift - Fearless

Breaking down and coming undone, it's a roller coaster kind of rush / And I never knew I could feel that much

May 16, 2025

Note: I will be including the original albums and the Taylor's Versions together, as I feel there's not enough difference to do two separate posts.

Release Date: November 11, 2008
Genre: Country, country pop
Label: Big Machine Records
Producer(s): Nathan Chapman

Release Date: April 9, 2021
Genre: Country, country pop, pop
Label: Republic Records
Producer(s): Christopher Rowe, Jack Antonoff, Aaron Dessner, Taylor Swift

My first three months of high school were some of the happiest and most exciting of my life. Suddenly, I was part of a whole new world, full of thousands of new people. The older ones I looked up to, the younger ones were potential friends. On top of that, I was still riding high from an incredible summer at camp, where I found my first serious boyfriend. Once camp ended, we lived far apart, but would talk on the phone almost every night. Then, in November, two earth-shattering events took place: he broke up with me, and Taylor Swift released her new album.

Taylor's timing couldn't have been better. Her debut record had a couple songs that seemed like they were written just for me, but this one had many more, and the quality was even better. Fearless is a collection of big, gleaming, irresistible songs about all the ups and downs of being a teenage girl, and it instantly became a favorite of mine. It showed that teen pop could still involve good, personal songwriting, though not everyone believed that at the time. Though she got lumped in with the wave of other stars like Miley Cyrus and (of course) the Jonas Brothers, she was doing her own distinct thing, and I liked it way more than the Disney-produced stuff. After months spent feeling like I was the only person who had heard of her, it was exciting to see her truly getting big and hearing her songs on the radio. Suddenly everyone was starting to see what I'd seen.

In case I haven't suggested it strongly enough, I absolutely love this album. I have loved it so long and so much that it's hard to explain exactly why. First, the production and mix -- Taylor's high vocals were a far cry from the deep and earthy ones you usually heard in country music, and her girlish range informs the blazing guitars, glittering strings, and dynamite choruses and bridges. The re-recording, over a decade later, benefits from sharper production and her sturdier singing voice. Taylor is, generally, equally as good at slow piano songs as she is upbeat radio-friendly fare, which helps this album thoroughly traverse so many facets of teenage relationships and growing up. Plus, it all feels like an album, with its consistent sound and recurring symbolism to tie it all together. It's cathartic, it's ecstatic… it's, well, you know.

Track by Track

Fearless: There are few sounds more satisfying than that snare hit and guitar lick that begin this album. We get one of its finest tracks right up front. The inviting acoustic verses and luminous imagery help set the scene, before the chorus goes into an all-out slam. Everything is crafted to replicate that head rush she describes, and it absolutely hits. The lyrics are classic Taylor, but unlike most of her songs, which were written from personal experience, these are imagination and fiction, which makes them even more impressive. Though it's not one of the most remembered hits from this album, it's a landmark one, raising the bar from her debut and blowing the doors open on the amazing journey to come.

Fifteen: If Taylor albums are stories, this song is the exposition. It introduces the main characters and looks back at their freshman year of high school. Musically, it's one of many wistful acoustic ditties on the album, and not the biggest earworm. Yet I had never heard a song like this before. Most songs, even Taylor's, have lyrics that zoom in on a single moment or situation. But this one is zoomed out, an entire movie reel of scenery in plain language. It was a single, but this one was never about a catchy hook; it's about that magical connection where Taylor seemed to be opening her diary, names and all, and reaching right out to her fans. I was 15 at its radio peak, and while my freshman year wasn't much like Taylor and Abigail's, it was comforting to turn on the radio and -- between all the songs about things I wasn't allowed to or couldn't do yet -- hear a story about where I was. It's not the showiest track, but I couldn't imagine the album without it.

Love Story: The lead single, and the one that created the image of Taylor that still lives in most people's minds. She is eternally Juliet, clutching her ball gown as she runs down the staircase, begging to escape this town. It used to be a bit hard for me to appreciate this song. The use of Romeo & Juliet felt cliché, and as a die-hard, I knew she had more to offer than the radio hits. Over time, I've come around to it, and I see why so many people find it so great. It works in many arrangements, as seen by how it's given new life on every tour. Even back then, I could admit there were some killer lyrics, my favorites coming in the second chorus. The guitar intro is a magic moment, as is the solo before the bridge. That it still gets played everywhere today and gets an enthusiastic reaction shows how timeless it is. I couldn't imagine this album, or indeed Taylor's career at all, without "Love Story."

Hey Stephen: This is a difficult one for me to judge, because it's one of her breeziest and most fun melodies ever, and the re-recording makes it even more so. On the other hand, my least favorite thing about her writing is when she resorts to silly gimmicks or puns, and it usually happens on these giddy crush songs. These verses are "You know how to ball, I know Aristotle" levels of lyricism. So ultimately, while it has juice, this isn't one I go back to often nowadays.

White Horse: The first sad ballad on the album, the turning point where the fairy tale shatters. It's not the flashiest, which makes it a bit of a sleepy listen, but I would say it's important for the album in its own quiet way (and it won her her first two Grammys).

You Belong With Me: The other big hit from this era, and another example of how she can spin a great song out of the tiniest spark of inspiration. This is another highly energetic number, with an even more fists-in-the-air chorus than "Love Story." It's about the most bummer of subjects, teenage unrequited love, yet it sounds like pure joy from start to finish. Every lyric is recognizable, not just that chorus. Every part drives along relentlessly. The video is the video of Taylor's early country career, no contest. Compared to "Love Story," I think it can get a little more annoying upon repeated listens, at least for me. But when you're fifteen, this is everything.

Breathe (feat. Colbie Caillat): This is the song I latched onto the most immediately after the aforementioned break-up. It's a somber and subdued acoustic number, the kind that made Colbie Caillat briefly famous. Unfortunately, despite the fact that her voice would have been perfect to do a verse on this, she provides backing vocals only. While I don't find this the most interesting song here, especially the oddly paint-by-numbers lyrics, it is very pretty.

Tell Me Why: Now we get into the angry stuff. This is one of the loudest and most country songs. Her voice wails over a frantic banjo. Even back then, I would always tell people her deep cuts were usually better than her singles, and it's this four-song stretch I was thinking of. It's also lots of fun to sing along to.

You're Not Sorry: To me, this and "Tell Me Why" are a pair. You can't have one without the other. It rounds out the album by giving us a "big" piano song, with a full orchestra and everything. It's her penchant for theatrics on the biggest scale, and even though it's slow, there is no chance of getting bored of it.

The Way I Loved You: For many years, this was my favorite song in Taylor's entire catalog, and it's still way up there for me. It's another loud, bombastic, even rock-tinged production with some of her most resonant lyrics. This song is eternal. It hits me the same way now, when I'm 31 and married, that it did when I was 15. I love my husband, but I'll never stop missing that guy from camp. And if you're into analyzing Taylor Swift songs as literary works, there are themes and questions here that will keep showing up throughout her discography: is conflict something you actually need in limited doses to keep a relationship alive? What kind of love is better, passion or safety? Is love burning red or is it golden? Some people take issue with the details of these lyrics, but thank goodness most of the fans get it. A wonderful hidden gem for the ones who know.

Forever & Always: One of the angriest songs on the album, and the one with the deepest lore, beginning a story that she would keep writing about for multiple albums to come. She wrote this by herself just weeks before the album went out, and that's probably why the verses are a bit rambling, taking a while to snap back to the chorus. The emotions are live and fresh, and she continued to air them out on TV and live performances for months after. The motif of rain continues, giving us the simultaneously grand and pathetic image of "It rains in your bedroom, everything is wrong." While I don't believe this is the absolute tightest song on the record, its immediacy still makes it pretty strong. I don't think the piano version is superior for this particular song, but it makes sense considering this is a break-up song. It's nice to get another version that's official rather than a fan-made one on YouTube.

The Best Day: After so many high-drama tracks, we get a breather. This is a gentle, sincere, and extremely sweet tribute to her mom, full of anecdotes from her childhood. Hindsight makes this one tug at the heartstrings even more.

Change: Speaking of hindsight, this song was inspired by the people at Big Machine Records, and how she felt when she won her first major award. This means a lot of fans have turned on it since the sale of her master recordings. But hating a song because of who it's about is dumb, and they're missing out. This is a triumphant banger, made even more so in the Taylor's Version by extending her final big note, and the lyrics are broad enough to suit basically any situation or interpretation. It was originally used as a promotional song for the 2008 Beijing Olympics. It could be a political rallying cry, especially considering the word "change" really was one of the slogan words for a political campaign at that time. But most of all, for all those girls listening who may have felt lonely or awkward or miserable in high school, it was a message to keep your head up, because soon you'll grow up and get to start over. In that sense, it's the perfect ending.

Jump Then Fall: Music fans often use the terms "bop" and "banger" to praise a song. Now is probably the time to explain that, for me, the words mean two different things. And some good songs are neither. Fearless has more bangers, but the first deluxe track, "Jump Then Fall," is perhaps the strongest example of a bop. The star of the show is a springy electric banjo that sounds unlike anything else in her discography. The whole result is jolly and effortless, just like the innocent summer love she wrote it about.

Untouchable: The only cover she's put on a proper album, and she reinvented it so thoroughly that many people don't even know it's a cover. (I certainly didn't for a long time.) The original is a fast, punk-ish rock song by Luna Halo, a band who briefly toured with Hoobastank during their post-The Reason era. This version fits right into Fearless' other lush, acoustic B-sides and vault tracks. The more the song goes on, the more it seems to fall into place. A really nice listen and a special window into her creativity.

Come In With the Rain: I find this to be one of the less successful songs here. The verses and pre-chorus have a lot of promise, but then the chorus slows everything almost to a halt. It still has its nice moments, though.

Superstar: This one is like a cheerier side to "Untouchable," a crush song with little tension, because she knew she'd never meet the guy. Doubtless she has by now, but the humility here makes it a really sweet song. Like many of these bonus tracks, I overlooked it the first time, and the re-recording helped me appreciate it.

The Other Side of the Door: Now here's another highlight, and one that's definitely been elevated by the re-recorded version and the tour. This whole song is made of the best that Fearless has to offer, painting vivid scenery in the lyrics and crescendoing into a super satisfying chorus. The last 30 seconds, though, takes it from very good to epic. She spits the outro so fast she's almost breathless, referencing so many prior scenarios: the fight on "Come in With the Rain," the lashing out on "Tell Me Why," the build-up of lies and secrets on "You're Not Sorry," and even further back, the guy's indiscretion on "Should've Said No." (Move over, Joe Jonas; that guy, whose name is too common to Google, was the real muse of Fearless.) A true high-water mark that's just as strong as any of the standard edition tracks.

Today Was a Fairytale: By early 2010, when this was a single, I was kind of like "Okay, Taylor, we get it with the fairy tales." But it's still good! It has that sweet, cheery, girlish sound that could have slotted easily into the front half of the main track list. Like "Love Story," I appreciate it more in hindsight now that I'm older and understand her songwriting better.

You All Over Me (feat. Maren Morris): This is another that's not popular with the fans. I think it's somewhat underrated -- the production is extremely pretty, and the lyrics are solid when you consider this was actually written for her debut album. But Maren Morris, like Colbie Caillat, is kept to backing vocals, and they don't really add anything to the song. It also doesn't have the momentum of her best ballads. It's a nice enough vault track but not a legendary one.

Mr. Perfectly Fine: Everyone's favorite vault track. Is it mine? It's fun, and heaven knows this vault needed something upbeat, but both the lyrics and the music are fairly one-note. When you hear ten seconds of the song, you've heard all of it. Still, it's an enjoyable Taylor song with a nice big chorus and especially bridge. It also adds more to the Joe Jonas story, a bridge between this and Speak Now. It does has a bit of that woozy Jack Antonoff hum that I don't think totally fits the album, but more on that later.

We Were Happy: A very slow, sad country song with a simple premise. This was also written pre-debut era, and though you can kind of tell, it's an okay enough mood piece. It's one of the ones I'm most likely to skip, but if you can make it to the bridge without tuning out, that is the best part.

That's When (feat. Keith Urban): This is a soft, intimate duet with one of the first big country stars to support Taylor. It's mid-tempo, and they don't overdo it. It follows the themes seen in some of the bonus tracks, but more level-headed. While Keith Urban does sound kind of weird here, and you could argue he doesn't belong on such a girl power album, I think this one is nice.

Don't You: Another extremely slow, mellow song about feeling tortured by seeing your ex after a break-up. As with many of these vault tracks written in her pre-debut days, it's decent but not a stand-out. But what really makes me conflicted is the production. Rather than sounding like anything from Taylor's early career, Jack Antonoff gave this a soft thrumming glow reminiscent of the synth-pop albums 1989 or Lover. This is controversial, especially among fans who think it's not okay to question any of the creative decisions, but I believe changing the production style this much is not in the spirit of the re-records. I've found fan-made mixes where this actually sounds like a Fearless song, with acoustic guitars, and it makes a difference. Sadly, this wasn't the last time this would happen with the vault tracks, but at least fans didn't already have attachment to this one.

Bye Bye Baby: The final vault track, and another one many fans seem to inexplicably dislike. For me, it's a lovely closer to wrap up the break-up story of the album. It's like another step of "White Horse," when the pain has dulled and she's working on moving on. It's a subdued, bittersweet, mid-tempo number that builds just enough in the bridge. Though written for the debut album, it has the maturity to conclude Fearless just fine. One of the nice things about these deluxe and vault tracks is it adds new pieces to the narrative, new ways the story may start or end. This finale is totally different than "Change," yet to me, works about equally well.

Crazier: I know this one is all but confirmed to be on Taylor Swift (Taylor's Version), but it was released on the Hannah Montana movie soundtrack in 2009, so on my spreadsheet it's in the Fearless column for now. It is very country, slow and steady, with one of those dreamy Taylor hooks. Her voice sounds very young, and the song overall has a more languid vibe than it probably should considering the subject matter, but it's fine considering her age when she wrote it and the understandable desire not to give away her best songs for movies.

Final Thoughts

Fearless is remembered as the album that launched a legend, and the songs are strong enough to justify that legacy. The hits really hit, and the deep cuts are usually just as good, rounding out the whole experience. It gave a fresh voice for teen girls, a demographic that wasn't always taken seriously in the world of mainstream music, but it also resonated with many outside of that demographic. It didn't perfectly capture the entire spectrum in that regard, because the label wanted to make sure she was relatively family-friendly, but it was a lot more than was usually heard on top 40. When she came on the radio, even my parents commented how it was so different that someone was writing songs so plainly about high school. There wasn't another artist around quite like Taylor, and I was so glad to have her.

As fitting of the artist perhaps most associated with the word "era," plenty happened for the couple years after this album's release. Obviously, there was the Kanye West VMAs incident, which was the first time I ever tuned in to the VMAs. It was pretty weird and surprising, but my classmates were definitely more focused on the memeable "Kanye did something crazy" aspect rather than thinking about the impact on Taylor. Two of my camp friends went to the Fearless Tour and I was hella jealous. Slowly but surely, she popped up more and more, in movies and magazines and tabloid covers. At some point -- probably around the time the lead single for the next album started getting airplay -- I realized she was here to stay.

As many Swifites can attest, whether Fearless is Taylor's best album depends what day you ask. But to me, it's unquestionably the most nostalgic. I'll be posting about all of her discography in time, but this one will always have a special place in my heart that nothing can touch. After all, you're only fifteen once.

Rating

So this is infuriating, because without the vault tracks, it would average to 4.07 and could get rounded up to ⭐️⭐️⭐️⭐️1/2. The album is a step up from her first record, as good as that was, and I want the numbers to reflect that. But the spirit of the Taylor's Version projects is that the vault songs are meant to add new dimension and enrich the album, and considering those songs are generally weaker and written earlier than the originally included tracks, they bring the full album down to ⭐️⭐️⭐️⭐️. Please know, though, that based just on the songs that did make the cut the first time around, this is high up there among the best albums I've posted here so far.

On my spreadsheet, I've put two different scores, with and without the vault tracks. I will continue doing this for future Taylor's Version albums. As I've said before, her catalog is special.

Synesthesia & Sugar

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