- John Wayne Gacy, Jr. by Sufjan Stevens
In this song, Stevens talks about John Wayne Gacy Jr, a serial killer from the 1970s. Gacy sexually assaulted and murdered 33 teenage boys and young men, and Stevens sings about the victims and brings to light the fact that they were actual people. Often, when we discuss these tragedies, we focus more on the people who inflicted them rather than the people who perished. The lines “Even more, they were boys/With their cars, summer jobs/Oh my God” really highlight this. Stevens ends the song by saying that deep down, he is really just like Gacy. This alludes to the fact that he, too, has dark secrets and can also be interpreted as the fact that all humans are capable of the things Gacy did. Overall, this song is heartbreaking, and the perfect song to listen to when you’re driving in the rain.
Sadness rating: 7/10
- If We Make It Through December covered by Phoebe Bridgers
This cover carried me through last December. A cover of Merle Haggard’s song released
in 1973, Phoebe’s soft, sad tone makes for a refreshing and melancholy rendition. It’s a song about being sad and struggling during what’s supposed to be the happiest time of the year, which really hit home for me (and probably many others) during last year, the first December of the pandemic. Phoebe’s entire Christmas EP provides a sadder take on a few popular Christmas songs, but this one in particular seems to hit the hardest.
Sadness rating: 8/10
- Marjorie by Taylor Swift
One of my all-time favorite Taylor Swift songs. In this song, Taylor sings about her grandmother, who passed away in 2003. The song even includes background vocals from her grandmother, who was also a singer and inspired Taylor to sing. It’s hard to pick out the most heartbreaking lyric, since they are all literally earth-shattering, but “I know better/But I still feel you all around/I know better/But you’re still around” probably takes the cake. It’s one of those songs I can’t listen to casually and often skip when it comes on because I know it’ll bring down my mood. It’s a beautiful remembrance of her grandmother and probably one of her most beautiful songs to date.
Sadness rating: 9/10
- Class of 2013 by Mitski
There has never been a time I’ve listened to this song and not cried. Mitski is known for her devastating songs, but this one feels like a punch to the gut every time. The song consists of nothing but a piano and Mitski crying out to her mother. She wrote this song around the time she was graduating from college (hence the title) and sings about being scared to go into the real world after graduation. I listened to this song a LOT during my senior year, and I feel like it perfectly captures the feeling of being scared for your future. When she sings, “Mom, am I still young?” I can feel it in my chest every time. Mitski will forever be the queen of sad songs.
Sadness rating: 10/10
- Writer in the Dark by Lorde
Another queen of sad songs. This song is incredibly raw and will always have a spot in my heart. “I am my mother’s child, I’ll love you ‘till my breathing stops” is one of my favorite lines of all time. While this song could be passed off as just another breakup song, Lorde is a genius, and her stripped-back vocals and devastating lyrics make this one of the best breakup songs of all time.
Sadness rating: 6/10