A Definitive Ranking of Taylor Swift’s Track 5 Songs, From Debut to ‘The Life of a Showgirl’

In 2014, a 24-year-old Taylor Swift was fresh off a situationship with big dreams and keys to her first New York apartment. As one of her first collaborative efforts with Jack Antonoff, the larger-than-life production on "All You Had to Do Was Stay" already sets it apart from her other track 5s. Although it's simplistic in its lyricism, the track paints a portrait (or, perhaps, a Polaroid) of the universal romantic whiplash most people endure by their mid-20s.

Between cutthroat reminders and pleading, "Stay" captures the emotional tug of war that comes with the "will they, won't they" nature of such relationships. And, sure, Swift doesn't stack up SAT vocab on 1989's fifth track, but that doesn't mean it loses all its meaning.

Best Lyrics: "People like you always want back the love they pushed aside / But people like me are gone forever when you say goodbye"

Reputation marked Taylor's comeback post-KimyeGate™, and while the album is bombastically vengeful as the artist declared that the past version of herself was dead, "Delicate" proves that the "Old Taylor" was still somewhere in there. The track marked a new beginning for the Track 5 legacy, focusing less on heartbreak and more on the fragility of opening up and letting your guard down in new relationships. Building up the ability to trust again is something anyone can relate to, and Taylor masterfully captures the waves of anxiety that come with acceptance.

Her Swiftisms shine through as she begs the question: "Is it cool that I said all that? Is it chill that you're in my head?" Plus, it doesn't hurt that it's still a crowd favorite at live shows thanks to the crowd's "1, 2, 3, let's go bitch" chant.

Best Lyrics: "Sometimes I wonder, when you sleep / Are you ever dreaming of me?"

With emotional tracks like "You're Not Sorry" and "Forever & Always," it's a wonder that "White Horse" earned the coveted track 5 spot on Fearless' tracklist. Through a fairytale analogy, Swift sits with the reality of her relationship and its disappointing downfall. However, the narrative doesn't lose hope—by the end of the song, she sees the bigger picture and projects big "Girl Who's Going to be Okay" energy.

It goes without saying that Swift's music transcends generations—whether you're 5 or 85, odds are you know more than a handful of her songs. The fact that my mom would listen to this song on a loop and post it on her Facebook wall every day in 2008 speaks volumes. "White Horse" has proven its staying power since its initial release thanks to a few factors, including a Stephen Colletti music video cameo and a duet with pop princess Sabrina Carpenter at the Eras Tour.

Best Lyrics: "My mistake, I didn't know to be in love / You had to fight to have the upper hand"

The second Taylor revealed the tracklist to The Tortured Poets Department, longtime fans knew it would be an emotional account of her relationship with London and her longtime love, Joe Alwyn. It's essentially the antithesis of Lover's "London Boy"—both lyrically and sonically—as she looks back on her connection to the person and place that became her home.

She opens up about wanting to build a life with someone and holding on tight with a "white knuckle grip" to keep the love alive through turmoil. "London" is heartbreaking and scathing all at once, which is something she continues to master throughout her career.

Best Lyrics: "You swore that you loved me / But where were the clues? / I died on the altar / Waiting for the proof"

I personally see "tolerate it" and "So, Long London" as two sides of the same coin. At the time, no one suspected that Taylor was likely referring to her relationship with Joe Alwyn on the evermore standout—and it still hasn't been confirmed—but with additional context several albums later, it's all starting to make more sense.

There's something incredibly disheartening about waiting for your partner with childlike wonder and excitement, only to be disappointed by the reality that they don't reflect that emotion. Taylor's theatrical live approach to the track on the Eras Tour only solidifies this song's stature as one of her best track 5s to date.

Best Lyrics: "I made you my temple, my mural, my sky / Now I'm beggin' for footnotes in the story of your life"

If you're looking for a track that outlines every Taylor Swift era until Midnights, "You're On Your Own, Kid" is exactly that. The song time travels to different points in her personal life and career through an introspective lens—it starts out with sympathy and ends with hope á la "White Horse." The first verse details the early aughts of a relationship, the second reveals Swift's songwriting "aha" moment, and the rest of the track unveils how her castle began to crumble and she found a light in her fans, music, and romantic relationships. And lest we forget that the track birthed the adorable tradition of making friendship bracelets for fellow Swifties?

This is a track 5 that we can put on when we need validation for our emotional journeys, complete with reassurance that everything will turn out how it's meant to.

Best Lyrics: "'Cause there were pages turned with the bridges burned / Everything you lose is a step you take"

Upon its release as a promotional single for Lover, people were quick to criticize this track as "boring"—which could not be further from the truth. Sonically, it's one of the best products that's come from her longtime collaborative relationship with Jack Antonoff. The stacked, echoed vocals represent an inner monologue ridden with anxiety as they sit atop a beat that heightens in speed throughout the song. The repetition of the lyrics by the bridge, where Taylor muses, "They see right through me, could you see right through me? I see right through me," feels like listeners are a fly on the wall during a panic attack.

The lyrics reflect on the human experience with a guilty conscience, almost serving as a warning for anyone who's willing to cross paths with her.

Best Lyrics: "And I cut off my nose just to spite my face / Then I hate my reflection for years and years"

Much of Speak Now walked so the rest of Swift's albums could run and ultimately win the race—and its fifth track is a prime example. "It was an album that was the most precious to me because of its vast extremes. It was unfiltered and potent," Taylor wrote upon its re-release in 2023, adding that "Dear John" is her "most scathing" song. It's one of the only songs in her career that actually name-checks its subject, although she denied it at the time of its original release.

"Dear John" is 6 minutes and 49 seconds of self-written Swiftian prophecy that is equally as heartbreaking and revealing as it is savagely ferocious. Long story short: she came on this bitch mad as hell, with a not-so-subtle nod to John Mayer's signature guitar licks.

Best Lyrics: "But I took your matches before fire could catch me / So don't look now / I'm shining like fireworks over your sad empty town"

There are plenty of ways "my tears ricochet" could be interpreted, but listening to it as a story of Taylor's battle with her former mentor, Scott Borchetta, over her original album masters changes everything. She hasn't explicitly confirmed whether this was the angle in which she approached the track, but certain lyrics (ahem, "stolen lullabies") could potentially point fingers in that direction. According to Jack Antonoff, this is one of the best songs Swift has written to date—not just a track 5.

"It's kind of a song about karma, it's a song about greed, it's a song about how somebody could be your best friend and your companion and your most trusted person in your life, and they can go and become your worst enemy who knows how to hurt you because they were once your most trusted person," Taylor said of the track during her Long Pond Studio Sessions documentary, adding that it's a story about the ultimate betrayal. She lets her guard down as she admits she didn't have it in herself to "go with grace," and removes a dagger when she muses, "If I'm dead to you, why are you at the wake?"

Whether it's performed with emphasized production in a stadium of 96,000 and counting, or a stripped-back version á la Long Pond, "my tears ricochet" goes down in history as one of Swift's best track 5s at a pivotal moment in her career where she's reclaiming her name and her reputation through her re-recorded albums.

Best Lyrics: "And I can go anywhere I want / Anywhere I want, just not home / And you can aim for my heart, go for blood / But you would still miss me in your bones"

We're going to pretend to be shocked that "All Too Well" snagged the top spot here. Even in a definitive ranking of Taylor Swift's best songs of all time, Red's fifth track almost always sits at No. 1, and with good reason. I don't need to tell you for the millionth time that this is Swift's magnum opus—it's one of the only things she and her ever-growing army of Swifties can agree on.

The official release of the 10-minute version proved that point further a decade later, and the standard version still holds up as a song that not only defines her legacy but serves as the national anthem for a generation's worth of heartbreak. And, all these years later, we're still wondering what happened to that damn scarf.

Best Lyrics: "You called me up again / Just to break me like a promise / So casually cruel / In the name of being honest"