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11 Saddest Taylor Swift Songs That Will Break Your Heart

Taylor Swift’s music’s brilliant lyricism and narrative-driven nature have made her a well-known singer and songwriter in the United States. Throughout the course of her professional life, she has experimented with a variety of genres.

There’s no denying that she’s one of the most excellent musicians of her generation, even though she might be regarded as Hollywood’s “undateable” sweetheart.

In this article, I’d like to take you through some of my favorite songs she is known for writing that are exquisitely depressing. Prepare your tissues as I count down the top 11 saddest songs of Taylor Swift of all time.

Saddest Taylor Swift Songs

1. Ronan

“Ronan,” recently released in “Taylor’s Version” by Taylor, opens the show. Before Taylor’s straightforward chords. The lyrics she sings are melancholy and haunting. The musician is a master of melody, creating simple pieces for her songs that are incredibly catchy and satisfying to listen to. Beautiful interplay will make you cry.

2. Last Kiss

If you thought that “Ronan” was the most depressing thing that had ever happened, you are gravely mistaken. One of the best – or perhaps worst – songs to listen to if you’re going through a challenging breakup is “Last Kiss,” which is a tragic farewell to the lover who got away. 

Expert Tip: This song’s melody and chord progression are pretty straightforward, but that’s the beauty of Taylor Swift’s music she doesn’t need to create intricate melodies and harmonies to make her point. In order for you to focus on the lyrics, she lets the music support her vocals.

3. I Almost Do 

You are encouraged to indulge in your feelings of melancholy for a short while by the song “I Almost Do,” which has a folky and almost country sound. There is a nice contrast between the sad lyrics and the nearly upbeat backing track characteristic of the sound associated with Taylor Swift.

The song “I Almost Do” is about overcoming the temptation to get back together with an ex-lover despite the knowledge that you and your exes will never be a healthy match for one another.

Like much of what Taylor sings about, this is something to which many of us can relate because she writes about the human experience. The human experience is a common theme in Taylor’s music.

4. All Too Well

The song “All Too Well,” with its delicate electric guitar arpeggios and gentle, persistent acoustic guitar strumming, will captivate you and submerge you in its melancholy from the moment the first note is played.

The verses sung in Taylor’s signature delicate tone are broken up by interspersed guitar solos that give this track an atmosphere reminiscent of country music.

It is not difficult to understand why All Too Well is considered one of Taylor’s most popular songs. This song will stay in your head for days, whether for the better or the worse because the chorus is so irresistibly catchy and the chord progression is so straightforward.

5. Come Back, Be Here

“Come Back… Be Here” by Taylor talks about wanting a lover we can’t have, which is a feeling we’ve all had.

Her country roots are evident in this song, which has a simple melody and classic chord progression. As you probably know, Taylor began as a country singer. It’s an iconic example of the country saying, “give me three chords and the truth.”

6. The Moment I Knew

“The Moment I Knew” is a piano ballad with a beautiful cello accompaniment. It’s similar to Taylor’s other works but also very different.

Taylor Swift’s verses are accompanied by a cello pseudo-countermelody. This emphasizes her lyrics. Epic instrumentation and Taylor’s powerful vocals pull at the listener’s heartstrings in the chorus.

7. Dear John

Undoubtedly, “Dear John” has a country vibe, harkening back to Taylor’s roots as a country singer. This song features prominent acoustic guitar work and is complemented by electric guitar riffs that add a touch of sonic soul.

Expert Tip: Taylor’s full vocal range is showcased in the song’s catchy melody, and the chorus features her more powerful register, making you want to sing (and belt) along. It would help if you played this on your long car rides.

8. Sad Beautiful, Tragic

Taylor Swift’s music is straightforward and easy to understand. The singer provides a contrast between sad lyrics and upbeat music with his or her performance. Consider the song “Sad Beautiful Tragic,” in which an acoustic guitar plays a chord progression and a second guitar plays a simple, lilting melody. It has no chorus. Instead of a break between verses, there is a brief musical interlude.

9. Breathe

Colbie Caillat’s incredible vocal abilities are showcased on “Breath,” and her duet with Sia creates a haunting, melancholy song that almost makes you want to get up and dance.
Another song that harkens back to Taylor’s time as a country singer, with its straightforward melody, effortless harmonies, and straightforward chord progression.

10. Never Grow Up

I wanted to end this list with a song from Taylor’s early days. “Never Grow Up” is a love song, but to a child. It describes the desire all parents have to keep their children young and innocent. It’s about the little things kids do that make us happy. “Never Grow Up” will move parents.

11. White Horse

Who cried to this song about a nonexistent ex? I first remember Taylor’s music video sobs. This song shows Taylor’s imperfect relationship. Not princes. “White Horse” self-blames for a failed relationship. “Stupid girl, I should’ve known,” and “My mistake, I didn’t know to love/fight” Taylor’s attitude shifts. Ex-lover grovels on the bridge.

Taylor is unapologetic. (I’ll find someone) She’s riding solo to be happy. Taylor is moving on without “White Horse” Fast!


Voilà. This has been fun, and hopefully, Taylor Swift’s saddest songs are behind her. She’s nearing marriage and, hopefully, long-term happiness. It would be nice if she stopped making lemonade from her failed relationships. She’s running on ever-older memories, so she should let go. Taylor, write happy things, and we’ll still love you.

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About Maggie Holding

Hello! My name is Maggie and I am a proud Editor/Author for PlayTheTunes. Coming From South Carolina, USA, my whole life I've sang and played the guitar and flute! I love music with a passion, and am ecstatic to help others in their own music journey!