Taylor Swift in 10 Songs

A crash course in the pop icon, from her self-titled debut to evermore

taylor swift in 10 songs
Taylor Swift, photo courtesy of the artist/Illustration by Steven Fiche

    Ever felt intimidated by a musician’s extensive back catalog? Been trying to get into a band, but you just don’t know where to begin? In 10 Songs is here to help, providing a clearcut entry point into the daunting discographies of iconic artists of all genres. This is your first step toward fandom — now all you have to do is take it.

    At the end of the day, trying to narrow down Taylor Swift‘s discography to just ten songs is a fool’s errand. Swift is one of a kind — by tapping into her own emotions and stories navigating young love, coming of age, and chasing big dreams, she carved her own niche in the country music genre before evolving into a pop star for the history books.

    Swift retooled the concept of fandom, too, using social media and her infamous “secret sessions” to connect with fans on a level rarely seen from artists her size. To maintain the level of success Swift has achieved for fifteen years is no small feat, either. At the end of the day, if you were to take away the tabloid stories and romantic drama, you’re left with an incredibly inventive, influential songwriter who has also been a vocal advocate for the rights of fellow artists.


    So many listeners grew up with Swift, and it’s been a joy to watch her explore different genres, styles, and sides of her identity as an artist and songwriter. She lets herself experiment, whether it was in the revenge-soaked reputation or the more mature, woodland escape of folklore and evermore.

    Ask ten Swifties to narrow her enormous discography down to ten songs to tell the story of her journey so far and you’d probably end up with a list of a hundred different songs. To that end, consider each track on this list a window into each era she’s offered us so far — there are so many gems in every album. (I tend to gravitate towards random b-sides, and could probably write an entire essay on “peace” if given the opportunity.)


    With Taylor Swift’s tenth album on the horizon, we tried our very best to highlight ten of the tracks that speak to her discography. While we wait for Midnights, due out for release on October 21st, enjoy this tour through her catalogue, from her self-titled debut to 2020’s evermore.

    Check out Taylor Swift in 10 Songs below, and scroll to the end for a playlist of every track.

    I Hope You Think of Me: “Tim McGraw”

    It’s the song that started it all: “Tim McGraw” was Taylor Swift’s debut single. Legend has it that Swift wrote this one while sitting in math class — daydreaming about a youthful romance while someone was trying to explain integrals? Relatable from Day 1!

    “Tim McGraw” is a bit timeless, in the way that many great country songs are. While the track was a proper introduction to Swift, with her vision as a songwriter and artist already so polished beyond her years, one of the most remarkable things about this song is when Swift performed it in front of Tim McGraw himself at the 2007 ACM Awards. Swift, all of eighteen years old, looked one of the biggest artists of the genre in the eye and nailed it. The album of the same name was still a few years down the road, but Swift was already pretty fearless.

    Count to Ten, Take It In: “Fifteen”

    Part of the reason many listeners are so attached to Taylor Swift is the fact that so many of us feel like we grew up alongside her. Swift has always had a knack for balancing personal details with more universal experiences, making it feel like she ripped a page out of her diary and laid it over a page from the listener’s own journal to write a song.


    “Fifteen” dialed into the experience of trying to navigate high school with that exact extremely personal energy. “Count to ten, take it in, this is life before you know who you’re going to be,” she says. When the time rolled around for Fearless (Taylor’s Version), an already emotional song took on extra poignancy — there’s something about hearing a woman, now in her 30s, reflect on a song she wrote in her twenties, about her teen years. The degree of removability, and the wisdom that comes with it, means that “Fifteen” continues to pack a punch to this day.

    Sparks Start Flying: “Enchanted”

    With such an extensive and rich catalogue, Speak Now sometimes gets lost in the shuffle. We all know Swift had a certain affinity for fairytale themes in her earlier work — something that hasn’t totally dissipated with time, only evolved — and “Enchanted” is one of the standouts from that time. Initially, Swift had imagined this song as the title track for the album, but she was advised to go in a more mature direction — there’s still plenty of youthful joy to be found in Speak Now, but “Enchanted” is one of the songs that starts to dip its toe in the waters of more mature territory.

    “Please don’t be in love with someone else/ Please don’t have someone waiting on you,” she pleads on the (stellar, per usual) bridge.

    We Remember It All: “All Too Well”


    There’s a reason “All Too Well” has taken on an almost mythological status within the Taylor Swift canon, only elevated by the recent accompanying short film. It is some of her very best work, with one of her very best bridges — whether you prefer the original or tend to gravitate towards the 10-minute cut these days, the best line to yell is still “you call me up again just to break me like a promise/ So casually cruel in the name of being honest,” and that will just never change.

    “All Too Well” remains a milestone in Swift’s discography and encapsulates so many parts of the Red era as concisely as possible. Red was a time of transition for the artist, and for many of her fans — it was the bridge between her country roots and her big pop dreams. It’s heartbreak, nostalgia, and hope for future. It’s the “miserable and magical” of growing up.

    Swift may have been in a relative in-between, but “All Too Well,” like so many parts of the Red era, underscores Swift’s greatest strengths. Her pen is her sword, and she knows how to use it.

    Nothing Lasts Forever: “Wildest Dreams”


    The dreamscape Swift designed within 1989 is electric and addicting. It’s New York City on its very best day, written through the lens of one very happy transplant. The front half of the record is just hit after hit — “Welcome to New York” kicks off the party, “Blank Space” cascades right into the effervescent “Style,” and “Out of the Woods,” “Shake It Off,” and “Bad Blood” all appear before we’ve even hit the halfway mark of the album. There, dead center, is “Wildest Dreams,” which boasts the kind of airy melody that gets trapped in the listener’s head and refuses to shake loose. It’s a very Taylor Swift move, and one she utilized in so many moments in 1989.

    Recently, TikTok prompted a resurgence of “Wildest Dreams,” which led to Swift re-recording the track as a standalone ahead of the full 1989 Taylor’s Version treatment. There are so many gems to choose from in this era of her work, but “Wildest Dreams” slides to the top of the pack.


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