The Significance of Taylor Swift’s Fearless in 2008—and How Taylor’s Version Stacks Up

Before the 11 Grammy wins, before cottagecore, before Joe Alwyn, before Cornelia Street, before the squad, before the legend of track 5, before the endless Easter eggs and memes, before the bad blood with Big Machine, Kanye West and Katy Perry—there was Fearless.

Fearless was Taylor Swift’s second album and the one that launched her into the mainstream proper in 2008. With megahits like “Love Story” and “You Belong With Me,” it spent 11 weeks atop the Billboard 200 and remains her best-selling album. Taylor was 18 when she released the record, and in accordance with teenagerdom, it captures BIG feelings: of love, heartbreak, ambition, growth, and more heartbreak. It’s a youthful project in so many ways, and sonically it’s undeniably dated: it captures a time when guitars were very much in vogue and 808s were still mostly a hip-hop tool.

But none of that has stopped Swift from re-recording and re-releasing Fearless 13 years later, as the start of a laborious and extremely public effort to own all of her masters. On the day of its re-release, the biggest Swifties at TIME gathered to reminisce about life before we knew who we were going to be, and to share reactions to the re-recording.

What did you think of Fearless when it came out? What do you think of it now?

Samantha Cooney: Fearless came out when I was a 14-year-old girl desperately waiting for my life to really begin. The songs captured the intensity of a period where every football game, AIM message or hallway glance felt like the most exciting thing to ever happen. I saw the songs as an emotional blueprint for my first love, first heartbreak, and other marquee experiences of growing older.

Now, at 27, I know life is more about the grey areas than the golden-hued extremes on Fearless. The world isn’t divided up into cheer captains and outsiders on the bleachers. The people who break your heart don’t deserve all of the blame. Love thrives in quiet moments, not in sweeping grand gestures in the rain.

But I still revisit Fearless when I find myself getting cynical just so I can remember how it felt to have my whole life ahead of me—to quote another Taylor bop—”back when I was livin’ for the hope of it all.”

Annabel Gutterman: As a passionate and annoying Taylor Swift fan, I rotate through her albums pretty consistently. But Fearless is the one that catapults me back in time like none of the others, so I tend to listen to it the least. Once I start, I have to listen to it in its entirety. It’s the one that surprises me the most—like wow, I still know all the words to these songs?

Fearless also introduced me (and surely many others) to the art of the break-up song. The fun of being a Taylor Swift fan is looking at how those songs evolve—and the different ways she accesses pain and the memories she associates with heartbreak. “Forever & Always” is a little deceiving—it’s so boppy!—and is all about the drama of being a teenager. The rain in the bedroom, just the idea of thinking someone is your “forever and always” when you’re just 15. In “All Too Well” (my favorite Taylor Swift song), she’s looking at that break-up at a bit more of a distance, picking apart the decidedly less dramatic parts of a relationship in such wrenching specificity: “We’re dancing ‘round the kitchen in the refrigerator light.”

Andrew R. Chow: As a surly Rolling Stone subscriber growing up in Manhattan, my taste in music skewed extremely male. I was busy mainlining Lupe Fiasco, the Raconteurs, the Cool Kids and the Strokes from my iPod mini, and Taylor’s princess-in-a-one-horse-town act didn’t really have any place in my worldview.

Or so I thought. After Fearless came out I would become infuriated when I realized I was unconsciously humming the melody to “You Belong With Me” at random hours of the day. The charm, gravity, and skillfulness of the album was undeniable; nearly every bridge lurched my stomach.

Chris Grasinger: I got into this album a bit late, sometime around Fall of 2009. I had recently moved to New York on my own and had just gone through a breakup with a longtime girlfriend. “Love Story” and “You Belong With Me” were pretty much everywhere at that point, but something compelled me to check out the entire album which I had not previously done for a Swift release. That’s the moment when I became a full-blown fan. Moments like “Breathe,” “White Horse” and “The Way I Loved You” connected with me like no other music at the time was able to. While my tastes were getting increasingly avant-garde, here was this popular crossover country album that just tapped into everything I was feeling.

I always looked back on it as a breakup album, but after re-listening now as a sappy 34-year-old, it’s a lot more. These days I’m really appreciating the more nostalgic moments about growing up like “Fifteen” and “The Best Day.” It covers a lot of ground: it’s equally great for crying it out on your floor and for joyous karaoke singalongs.

Raisa Bruner: Can I confess something? I had never listened to Fearless all the way through, with intention, until this week. I was not “into” Taylor Swift when this came out, or for many years after. I thought she was silly: all that singing so obviously about boys and basic high school things. (In 2008, I was going through an indie phase and looked down upon Top 40 taste.) The irony is that listening to these songs now—especially “Love Story” and “You Belong With Me,” the most familiar ones—I relate more than I would have as a teen. When this album came out, my experience with love was relegated to unrequited crushes. Now, every lyric has two layers: sure, there’s the teenaged Taylor, but they’re all really simplified analogies for adult heartbreak and frustration, aren’t they? On the heels of a lonely pandemic year of nostalgia and yearning, that hits with new sharpness.

Do you have any specific memories attached to Fearless from 2008?

SC: Dancing around to “You Belong With Me” in my childhood best friend’s basement while she’d try to drown me out with Weezer’s “Beverly Hills.”

AG: These were the songs of my sleepovers—I remember a large group of us re-enacting “You Belong With Me” on my friend’s staircase and pretending we were in a music video.

ARC: Watching the Grammys and being secretly happy that she won Album of the Year. (Although looking back at the best album nominees—what an absolute joke! I demand justice for TV on the Radio’s Dear Science.)

CG: Is playing it over and over while crying in my apartment specific enough?

What is your favorite song on Fearless and why?

AG: Because I was not yet in high school the first time I listened to Fearless, I considered it a road map of sorts for how things would go. There would be boys and bleachers and so much screaming and crying! And there were definitely all of those things. But what I didn’t expect was to feel so nostalgic about it all as it was happening because I knew that I would miss it all. Taylor Swift warned me to please pay attention! And that brings me to “Fifteen.”

I was 12 years old when Fearless came out and absolutely desperate to turn 15 so I could feel like the song applied to my life somehow, in a self-fulfilling prophecy kind of way. And while there was the expected amount of heartbreak that accompanied high school, what stuck out to me (and still does) are the lines about Abigail who is much more the main character of that song than the boys will ever be. “We both cried” hits me in the gut every time—the image of high school best friends carrying each other through that moment that seems like the biggest drama that will ever happen to them in their entire lives. After I turned 16, my best friend and I had a sleepover and wept so many tears because suddenly I was “so old” and obviously could no longer relate to “Fifteen” and all its youthfulness.

Little did we know that for basically every year to follow we’d reference that song for each of our birthdays and declare that “Fifteen” still applies to us, because it belongs to us, and it always will.(And we still do this, even after we turned 22).

CG: I’m going with “Breathe” because of emotional attachment (and I’m a sucker for her ballads) but the best song here is probably “Love Story,” which is truly incredible and likely the song that got me into her music in the first place.

RB: “You Belong With Me.” Maybe I’m just going through it right now? Maybe I just deeply relate to the experience of being overlooked? (Oof.) Or maybe I just prefer that power-pop punch? It feels like angst and release; it feels like screaming in the wind.

ARC: I love how incredibly twee and dorky “Hey Stephen” is. You know that Taylor these days wouldn’t be caught dead rhyming “Stephen” with “deceivin’” or “angel” with “kiss you in the rain, so.” “The Way I Loved You” is also a vintage example of the “Taylor Falling For Bad Boys” trope that she would go on to mine so much great material from.

SC: “Forever & Always.” It has everything: lyrics you can scream (“Did I say something way too honest?”); the perfect amount of specificity to allow you to both feel her pain and apply the sentiments to your own romantic tribulations; and the ‘who’s this song about?’ intrigue (Joe Jonas). It’s the archetype for a classic Taylor Swift break-up song.

Where does Fearless rank in the TSwift catalog?

SC: I think Fearless is an essential text in the Taylor Swift curriculum—it’s the album that made her a star. But I don’t find myself revisiting the album or its songs unless I want to bring myself to a certain nostalgic place.

I’d rank it sixth behind 1989, folklore, Red, Reputation, and evermore. Her later work has, on the whole, far better vocals, more nuanced lyrics, and more emotional weight. (And no, I will not apologize for loving Reputation—listen to “Getaway Car” or “Call It What You Want.”)

ARC: I think this one holds up really well! There are some songs that are just so unabashedly 2008 (“Forever & Always” splits the difference between The Fray and Metro Station). But the melodies are sturdy, and the sheer exuberance and wide-eyed wonderment she imbues into the project are undeniable. Depending on the day, I could push it as high as second (behind Folklore).

AG: My rankings are pretty fluid, the only thing that doesn’t change is that Red is always at the top. Right now (and mind you after a year of an extremely large amount of new Taylor Swift content) this is where I’m at: Red, 1989, Evermore, Speak Now, Fearless, Folklore, Lover, Reputation Taylor Swift.

I feel like people who like Evermore more than they like Folklore probably are more into Fearless. Because nostalgia!

CG: A close second right behind 1989. But definitely the album of hers that I have the most personal connection to.

RB: I’ll be the weirdo who definitely prefers her most recent work over the older stuff—to me she’s only gotten better with age, particularly in the complexity of her production and lyricism. (Folklore, Evermore and Lover are the projects I return to most.) Fearless sounds like a product of its time. And yet its youthful intensity—and musical delicacy—means it beats out the self-titled album, Red, 1989 and Speak Now for me. Is that blasphemous? I’m a sucker for a fiddle, sorry!

How does the re-recording sound to you? What sounds different and what sounds the same?

AG: The re-recording wrecked me just like I knew it would. There’s something really special about listening to Taylor sing these songs knowing the huge distance between where she is now and who she was when she wrote them. I keep coming back to the very last part of “Fifteen.” In the original, “I didn’t know who I was supposed to be” fades into the end of the song. In the re-recording, it’s more pronounced—and takes up the space to be hopeful and haunting all at the same time.

I need a few days to process the songs from the vault (because, like I said, I am an annoying Taylor Swift fan). I’ve spent enough time with “Mr. Perfectly Fine” to know that I love it—it’s a punchy break-up anthem with the 2008 boys-are-everything energy that Taylor captures so well. Also, I’m choosing to believe that when I listen to “All Too Well” that the origins of “casually cruel” have something to do with Joe Jonas.

CG: I think the new versions sound great. I’ll always love the original recordings because that’s how I learned these songs, but the differences seem pretty subtle. Some of her inflections are different, and I find myself thinking that a certain part should be faster or whatever, but those little things make me glad both exist. It’s kind of similar to the feeling of listening to a live album. There is also a refinement to these new versions that likely only comes from playing them over and over on tour since 2008. After having such a big 2020, it feels pretty special to be able to hear her revisit these songs that she wrote and recorded over 12 years ago.

As far as faithful re-recordings go I think she did a great job. Colbie Caillat coming back to do “Breathe” is a nice touch too. I think this will be the version of Fearless I’ll be playing from now on. Plus, having all of these extras and From The Vault tracks in one place is pretty awesome.

ARC: I completely respect Taylor’s decision to re-record this album from a political, personal and economic perspective—but musically, I’m struggling a bit here. Listening to this album, I feel like I understand Capgras delusion; I feel like David Byrne screaming, “This is not my beautiful house!”

Everything is the same but different; everything is drenched in slightly more reverb, whereas the original recording had a really pleasant crispness to it. And because the record is so close to the original, the micro-moments she changed have me doing psychological somersaults, whether the omission of the pitter-patter hi-hat fill 20 seconds into “You Belong With Me” or the giggle-turned-cackle after “Hey Stephen”’s last verse.

And then there’s the matter of Taylor’s voice itself. She is undeniably a better singer after 13 years of experience and vocal lessons; her voice is more expansive, warmer, and less shrill. But to me, her improvement puts her at a remove from the jagged edges of her teenage material. When she sings “it’s the first kiss, it’s flawless, it’s really something” on Fearless, she now sounds wistful as opposed to viscerally reliving a moment from a year or two ago. She’s unable to recapture the aura of complete freedom on the syllables “hey isn’t this eeeeee-eezay?” on “You Belong With Me.” And when she originally sang about her 13-year-old friends being “so mean” on the “The Best Day,” the line was followed by a sharp inhale, as if she was about to break into tears; on the new one, she controls her breath and glides over the syllable with too much control.

This is all extremely nitpicky; I’ll probably end up listening to the new one going forward regardless. But there’s a reason this exercise has never been done before: no matter how hard you try, it’s impossible to fully embody a previous version of yourself.

SC: In the original songs, you can hear her anguish as she begs for boys to choose her—or give her a reason why they can’t. That’s missing from the new versions. Instead, the songs are imbued with a sweet wistfulness for the messiness, vulnerability, and softness of youth.

This new perspective enhances a lot of these songs for me. I never really loved “Fifteen” growing up (sorry Annabel!), writing it off as a bit too schmaltzy for my taste. But I really love this new version, especially since we know that in the decade-plus since the original release, Swift did achieve some things in life “greater than dating the boy on the football team.” (As did many of the former teenagers taking in these tracks now!) But I did miss the breathless excitement and heartache on songs like “The Way I Loved You” and “Tell Me Why,” which are about the youthful desire to pine for a boy you know will mistreat you.

But overall, I love that this re-recorded album is essentially a love letter to being a teenage girl. The world still dismisses teenage girls as not serious enough, too dramatic, and overall too much. Adolescence is often looked back on with embarrassment and shame. But these songs make me want to give my former 14-year-old self a hug and tell her she was doing just fine.

(On that note, 14-year-old Sam would like to burn the brazen vault track “Mr. Perfectly Fine” onto a mix CD with “Pieces of Me,” “Take a Bow,” and “Since U Been Gone” and dance around my childhood bedroom.)

RB: The new Fearless is long. There are six new songs “from the vault” (and Maren Morris! And Keith Urban! and a piano persion of “Forever & Always”). This is all for the fans. Taylor sounds different now, of course; her voice is deeper, truer. The production is crisper. It’s the new songs that ultimately are catching my ear; the re-recordings feel like she is retracing old territory, cautious not to rock the boat with change. These vault tracks have the chance to feel and sound freshest, despite some rather uninspired lyrics—“Sometimes I really wish that I could hate you,” off “Don’t You,” makes me glad Taylor honed her craft further in the intervening years. But “We Were Happy”? So pretty! “Bye Bye Baby”? Sounds like Taylor is singing into my ear; it’s more intimate than the rest of the album, a warm ending note that makes me look forward to whatever Taylor else has up her sleeve. She’s not reinventing the wheel, but there’s joy in rediscovery, too.