Along with her catchy pop hits and vengeful breakup anthems, Taylor Swift has a catalog of devastating songs. While she is known for writing about love, Swift has written songs about various topics.

Whether a heartbreaking split or a difficult life event, the singer-songwriter has channeled these sad emotions into music. Swift also certainly has a few albums that were much more upbeat than others.

Her 2014 record 1989 was inspired by her move to New York City and all the time she spent with her female friends. Her following album reputation also used heavy production and was mostly filled with revenge anthems and love songs. However, even her romance-filled album Lover has a few heartbreaking songs on it.

Some of her saddest songs came from folklore and evermore, and were mostly fictional. Whether based on her lived experience or not, the following Taylor Swift stand out as some of her saddest.

Would’ve, Could’ve, Should’ve

Midnights (3am Edition) (2022)

After dropping Midnights on October 21, 2022, Swift released the 3am edition with a few bonus songs. One of these tracks was “Would’ve Could’ve Should’ve.” The song called back to some of her earlier work, including Speak Now’s “Dear John.” In both songs, Swift sings about being 19 years old and feeling manipulated by the man she was in a relationship with. However, the saddest part of “Would’ve Could’ve Should’ve” comes at the bridge when Swift seems to be begging for someone to set her free from the pain this man caused her.

The lyric that pulled the most at Swifties’ heartstrings was, “Give me back my girlhood. It was mine first.” It quickly went viral on TikTok, with young girls sharing their own stories about being taken advantage of by an older man. Swift seems to be crying out for help throughout the whole song. While there are many moments of anger, underneath the fury is deep sadness from someone who is finally coming to terms with what happened to her.

9 Last Kiss

Speak Now (2010)

Every July 9, Swifties celebrate the annual “Last Kiss” day. Taylor Swift even sings the ballad as a surprise song when she has a show on that date. The celebration comes from the song’s lyric “that July 9th, the beat of your heart.” It’s pretty agreed upon that “Last Kiss” is one of Swift’s saddest breakup songs mostly because of the melodies and her tone of voice. Of course, there are some chilling lyrics that add to its sadness as well.

Throughout the ballad, Swift has no anger in her voice but a deep devastation that this relationship has ended. As Swifties know, Taylor Swift knows how to write a bridge and the bridge of “Last Kiss” is especially heart-rending. In the bridge, she comes to terms with the fact that this person is no longer in her life and all she can do is watch him from afar.

“I hope the sun shines and it’s a beautiful day

and something reminds you you wish you had stayed

you can plan for a change in the weather and time

but I never planned on you changing your mind.”

She compares watching his life through pictures to the way she used to watch him sleep. What Swift has always done best is make her personal experiences feel universal and “Last Kiss” is a song that feels relatable to people of all ages. The lyrics are also more mature than some of the songs she’d written on previous albums.

8Never Grow Up

Speak Now (2010)

“Never Grow Up” is an especially nostalgic song as Swift sings about various stages of life. From being a young baby falling asleep to a 14-year-old embarrassed to have her mother drop her off at the movies, Swift covers the different stages of growing up. “Never Grow Up” is certainly a tear-jerker as Swift sings about her resistance to growing up despite knowing it’s an inevitable part of life.

The second verse is especially sad as Swift acknowledges that while she is growing up, her mother is also getting older. This ties into the song’s saddest lyric at the end of the bridge: “I just realized everything I have is someday gonna be gone.” As Swift sings about in the post-bridge verse, the inspiration for the song came from her moving out of her parents’ house into her own apartment.

She sings about feeling cold and lonely in her new place before the final chorus where she is pleading to go back to when she was a kid. The message of “Never Grow Up” is also pretty universal and while it’s sad, it also pushes listeners to appreciate what they have instead of wishing it away.

7 Bigger Than The Whole Sky

Midnights (3am Edition) (2022)

Swift never gave an explanation of what “Bigger Than The Whole Sky” was about but the lyrics point to a great loss. Swift blames herself throughout the song, believing it was something she did wrong that caused her to lose whatever she is singing about. Lyrics like “every single thing I touch becomes sick with sadness” and “I’m never gonna meet what could’ve been, would’ve been, what should’ve been you” are among the saddest.

While several interpretations have surfaced online, the song has resonated most with women who have experienced miscarriages. Throughout the song, Swift sounds hopeless as she tries to come up with a reason for her loss. No matter what Swift’s intentions for the song were, it’s incredibly powerful that she was able to touch women going through such a painful and vulnerable situation. No one could understand such a loss, but Swift was able to put this feeling into words.

6 All Too Well (10 Minute Version)

Red (Taylor’s Version) (2021)

“All Too Well” instantly became one of Swift’s most heartbreaking breakup songs when she released Red in 2012. However, the extended version only made the song sadder.

From added verses, a lengthened chorus, and a new outro, Swift gave more introspection into what she was going through. Swift’s sadness was always evident but this time she was digging deep into how manipulated she felt by the relationship and how blindsided she was when it came to an end. It became clear that the song’s title was actually Swift trying to reassure herself that the relationship really did happen.

In the end, Swift finds herself asking her partner over and over again if he remembers it all like she does. “Did the twin flame bruise paint you blue, just between us did the love affair maim you to,” showcases Swift’s need to find out the truth. The raw emotion that shines through from start to finish of “All Too Well” is why it’s become one of her most popular songs.

5 Tied Together With A Smile

Taylor Swift (2006)

Swift’s first album is often looked at as less complex than her later work. However, Taylor Swift had one of the singer’s saddest songs to date. Swift wrote “Tied Together With A Smile” when she found out one of her friends had an eating disorder.

The songwriter admitted she thought her friend was absolutely beautiful and she couldn’t believe what she’d been dealing with behind the scenes.

Body image might not be something Swift sings about often but it is a prominent subject among young women. Since Swift has so many young female fans, it was incredibly important that she put this song out into the world.

Swift sings about a girl who doesn’t see her own beauty and is constantly searching for love in other people. The lyric “you’re tied together with a smile but you’re coming undone,” suggests Swift’s friend looked perfect on the outside but on the inside, she was falling apart.

Swift’s sadness comes through as she sings, with her voice nearly breaking on multiple occasions. When Swift performed the emotional ballad as a surprise song on the reputation tour, she gave an empowering speech encouraging fans to be kind to themselves and not make assumptions just because someone’s life looks perfect.

4 Epiphany

folklore (2020)

While many of the songs on folklore were inspired by books Swift read or movies she watched during the Covid-19 lockdown, a few were inspired by real-life events. Swift discussed the message of “Epiphany” during Folklore: The Long Pond Studio Sessions.

In the song, Swift considers the way nurses working in hospitals during the pandemic were going through something so traumatizing that they might never speak about it again. Swift compared this to the way her grandfather would never speak about the things he experienced while fighting in World War II.

“Holds your hand through plastic now

Doc I think she’s crashing out.”

While the worst thing the average person was experiencing during lockdowns was being bored in their house, Swift’s song puts into perspective what it was like to be on the frontlines. Swift can tap into a situation she hasn’t experienced herself through her own deep compassion and empathy. She also sings about the hope that there will be some epiphany to save everyone from one of the darkest times in modern history.

3 Marjorie

evermore (2020)

Another real-life song that came from the folklore-evermore era is “Marjorie.” Swift has spoken about her grandmother Marjorie Finley a lot throughout her career.

As an opera singer, Finley was one of Swift’s biggest musical inspirations. However, the evermore track is the first time Swift ever sang about her grandmother in one of her songs.

Throughout the verses, Swift sings about the lessons she learned from her grandma.

She also has her grandmother’s vocals playing on the track as she sings the lyrics “If I didn’t know better I’d think you were singing to me now.”

However, like many of Swift’s songs, she saves the saddest lyrics for the bridge. It’s here where she states her regrets like the time she complained during a day trip and all the times she didn’t ask her grandma enough questions about life.

Swift also regrets not keeping everything her grandma owned, even things as simple as grocery receipts.

Swift concludes with the understanding that while her grandma isn’t physically here anymore, she still feels her all over. One of the most beautiful moments from the Eras Tour was when Swift performed the song and the audience turned on their phone flashlights, illuminating the stadiums and honoring Swift’s late grandmother.

2 Ronan

2012

The first time Taylor Swift ever released a song about cancer was for a young boy named Ronan who died at only four years old. Swift had found out about him from his mother, Maya Maria Thompson’s, blog posts.

She’d later form a friendship with her, inviting her to her concerts and meeting with her backstage. Swift released the song in 2012 and performed it for the first time at a Stand Up To Cancer event. Swift listed Thompson as a co-writer since many of the lyrics came from things she had written on her blog.

The song chronicles Ronan’s childhood where he’d play with dinosaurs, dance around before bed, and jump on his mother in the mornings to wake her up.

However, the song also references escapism, creating a fantasy where Thompson and Ronan could fly away together to a world where he wasn’t sick. Swift also touches on the devastation that came when Ronan passed away.

Much like “Bigger Than The Whole Sky,” Swift addresses the frustration of not understanding why something so bad had to happen.

1 Soon You’ll Get Better

Lover (2019)

Lover was a mostly optimistic album about her long-term relationship and stepping out of the darkness of the reputation era. However, Swift slid a few sadder songs onto the tracklist, one of them being “Soon You’ll Get Better.” Swift first opened up about her mother’s cancer diagnosis during the 1989 era. However, she didn’t address it in music until Lover. Swift sings about the denial and devastation of learning about her mother’s cancer. She sings about doctor appointments, praying for her mother’s healing, and doing anything to make her feel better.

The chorus is a plea for her mother to get better because Swift doesn’t know what she would do without her. The singer-songwriter has spoken extensively throughout her career about how much her mom means to her and wrote the Fearless track “The Best Day” about her. In the bridge, Swift confesses her guilt over making the situation about herself but wonders what she would do or who she would talk to if her mother wasn’t there.

It’s one of Swift’s most personal songs but it’s also one that deeply resonated with her audience. Taylor Swift swore she’d never sing it live because it was too emotional. However, she ended up performing it during the 2020 One World: Together at Home concert in honor of those who had lost loved ones to the pandemic.