“You Don’t Get To Tell Me About Sad”: Taylor Swift’s 10 Saddest Songs, Ranked

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.

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.

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.

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.