Ranking Every Track 5

Whether you’re a seasoned Swifitie or just joined the community, you may have noticed a pattern with Taylor’s albums. It’s been a tradition since her very first album that she purposefully puts her saddest songs on track 5! And today I am going to rank what I think are the least heartbreaking track 5’s to the most heartbreaking!

Let’s have a refresh on each track 5 before we begin!

Debut - Cold As You

Fearless - White Horse

Speak Now - Dear John

RED - All Too Well

1989 - All You Had To Do Was Stay

reputation - Delicate

Lover - The Archer

folklore - my tears ricochet

evermore - tolerate it

Midnights - You’re On Your Own, Kid

The Tortured Poets Department - So Long, London

The Life of a Showgirl - Eldest Daughter

12. I think this is already going to cause some friction, but let me make my statement. I have been a stan of this song since the minute I heard it. I love this song, so by giving it my least saddest track 5 doesn’t mean I don’t like this song. I’ve never been able to see it as a sad song, though. I see it more as a hopeful love song than a heartbreaking ballad. Delicate takes my number twelve spot as the least saddest song in my track 5 list. Lyrics include: Dive bar on the East Side, where you at? Phone lights up my nightstand in the black // Come here, you can meet me in the back // Dark jeans and your Nikes, look at you oh damn, never seen that color blue // Just think of the fun things we could do 'cause I like you

11. Ya’ll, this is harder than I thought! Two songs were competing for this number. As awful as that sounds, it only means one song will come out on top, closer for the saddest track 5, right? My next pick for the least saddest track 5 is All You Had To Do Was Stay. I know that this is a breakup song, but the upbeat tempo makes it so hard for me to rank it higher in terms of the most heartbreaking track 5. Lyrics Include: Here you are now, calling me up, but I don't know what to say // I've been picking up the pieces of the mess you made // People like you always want back the love they pushed aside // But people like me are gone forever when you say goodbye

10. We can chat about this pick in the comments. This song went head-to-head with number #9. I’m gonna be real honest with ya’ll, I’ve never been a HUGE fan of this track 5. The only reason I’m going with #10 for this is the bridge and how devastating it was for a first album and for the first track, 5, that started it all. Cold As You gives a heck of a bridge and that’s exactly the lyrics I’m going to include: You never did give a damn thing, honey but I cried, cried for you // And I know you wouldn't have told nobody if I died, died for you // Died for you

9. I ugly cried watching this music video the first time I saw it; the emotions were too raw for ten-year-old me. I hate putting this track 5 in 10th place, but Taylor just kept writing sadder and sadder songs, so don’t blame me. White Horse is our #9, and I’m gonna say if Taylor re-released this song with her sobs in the background from the music video, this would go straight to number one, I’m not even joking! Lyrics include: Maybe I was naive, got lost in your eyes and never really had a chance // My mistake, I didn't know to be in love
you had to fight to have the upper hand // I had so many dreams about you and me happy endings, now I know

8. I’m starting to wonder why I even came up with this blog post in the first place. I’m one thousand percent going to get heat for this, but I simply don’t have another choice, and ya’ll we know as Swifties that our track 5’s change depending on what season of life we’re in, so don’t come after me. I have to go with Eldest Daughter for #8. I love her; she is so insanely heartbreakingly beautiful, and that bridge scratches the itch! Lyrics include: You know the last time I laughed this hard was on the trampoline in somebody's backyard I must've been about 8 or 9 // that was the night I fell off and broke my arm // Pretty soon I learned cautious discretion when your first crush crushes something kind // When I said I don't believe in marriage that was a lie // Every eldest daughter was the first lamb to the slaughter so we all dressed up as wolves and we looked fire

7. You know how there’s that one song from your past that you associate with a very unpleasant memory, and when it comes on, your stomach kinda turns, and you wanna throw up a little? Okay, so not to get into the details, but this is that song for me. For our newer Swifties in the audience, Taylor also may or may not talk about the eating disorder she had during the 1989 tour, so there’s a reason this song beats out Eldest Daughter. The fact that this is basically The Eras Tour is one song makes me want to bawl, so You’re On Your Own, Kid comes in at #7 ! Lyrics include: From sprinkler splashes to fireplace ashes I gave my blood, sweat, and tears for this //
I hosted parties and starved my body like I'd be saved by a perfect kiss // The jokes weren't funny, I took the money // my friends from home don't know what to say // I looked around in a blood-soaked gown and I saw something they can't take away

6. I understand this song in a whole new way now than I did when it came out and let’s just say it’s a hard song to get through but also shout out to Trav before we even knew 87 would steal our girl’s heart 🫶🏼 The Archer hits me in the feels every. single. time. Taylor keeps repeating, "Can you see right through me?” Hinting at the anxiety she felt, she asked her significant other at the time if they could see her insecurities. The song also explores themes of self-sabotage, and we see Taylor’s deepest fears in its lyrics. Lyrics Include: I wake in the night, I pace like a ghost the room is on fire, invisible smoke // And all of my heroes die all alone // Help me hold onto you // I've been the archer I've been the prey // Screaming, who could ever leave me, darling? But who could stay?

5. This one made it to the top 5 because the emotion in Taylor’s voice is unmatched. This song is perfect in every way: the vocals, the instrument choices, the lyrics, and the tone. Cue the rain coming down, because I think Dear John makes all of us feel certain things. Unpopular opinion: I LOVE hearing Taylor’s mature vocals on “Speak Now (Taylor’s Version)"; it’s stunning! Lyrics include: You are an expert at sorry and keeping the lines blurry never impressed by me acing your tests // All the girls that you've run dry have tired lifeless eyes 'cause you burned them out // 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

4. Ya’ll knew it was coming, so I’m just gonna come out and say it, hello All Too Well! I’m literally kind of upset that Tay didn’t swap out All Too Well for All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault) when she let out RED (Taylor’s version). I must have burnt out my CD so much because I just kept listening to this song over and over again. Lyrics include: Time won't fly, it's like I'm paralyzed by it // I'd like to be my old self again but I'm still trying to find it // After plaid shirt days and nights when you made me your own // Now you mail back my things and I walk home alone // But you keep my old scarf from that very first week 'cause it reminds you of innocence and it smells like me // you can't get rid of it 'cause you remember it all too well

3. I think I can speak for all of us when I saw how we loved Taylor and Joe’s relationship, and the songs that came from their love were ICONIC. To go from Call It What You Want to So Long, London is damaging! I am obsessed with the beat and the pain in the lyrics. Yes, I love sad songs, no, I don’t think it’s bad. Taylor writes in detail about how awful the end of the relationship was and gives fans insight into why the couple broke up. The imagery in “And you say I abandoned the ship but I was going down with it my white knuckle dying grip
holding tight to your quiet resentment…..”

2. Rumored to be written about Taylor’s old record label manager, Scott Borchetta, this song deserves to be at #2. If you don’t know the story of My Tears Ricochet, Taylor left Big Machine Records in 2018, the label she had been with since her first album. Scott Brochetta sold Taylor’s musical catalog to Scooter Braun, someone who continuously bullied Swift the last few years. Though this song holds a lot of heartbreak and pain from what was once a good relationship, it’s okay because, as of May 2025, Taylor was able to buy back her masters. Lyrics include: I didn't have it in myself to go with grace 'Cause when I'd fight, you used to tell me I was brave and if I'm dead to you, why are you at the wake? Cursing my name, wishing I stayed look at how my tears ricochet

1. The time has come, and that means we only have one song left. This was incredibly difficult, but I think this song deserved it because of the damaging lyrics, Taylor’s tone, and the overall animosity of the song. The saddest track 5 of all track 5’s is tolerate it. Taylor wrote this song about someone in a one-sided relationship in which one person is emotionally neglectful. Swift said she was inspired to write this song after reading Rebecca by Daphne du Maurier. This song is poignant and Taylor such brilliantly expresses how someone would question and beg their partner in this kind of relationship. Lyrics include: While you were out building other worlds, where was I? \\ Where's that man who'd throw blankets over my barbed wire? || I made you my temple, my mural, my sky now I'm begging for footnotes in the story of your life