[2026] A roundup of dark Western songs I'd like middle schoolers to listen to
When we’re weighed down by melancholy, it’s the power of music that gently wraps around our hearts.
Sometimes we feel deep empathy by laying bare the darkness inside; other times we find encouragement amid despair—here are some classic Western songs that do just that.
Focused mainly on Gen Z artists, we’ve selected tracks that can stand beside the many kinds of emotional pain today’s middle schoolers (as of 2025) may face—heartbreak, friendship troubles, anxieties about the future, and more.
Listening while understanding the lyrics will make them resonate even more deeply.
Just be careful not to get swallowed by darkness that’s too deep—and by all means, try listening as you read the lyrics.
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[2026] A Compilation of Dark/Depressing Western Songs for Middle Schoolers to Listen To (61–70)
All of the StarsEd Sheeran
This song, created as the ending theme for the film “The Fault in Our Stars,” is a love ballad about longing for a distant lover.
With the autumn sky so high, it’s only natural to feel the distance between you and the one far away.
Both the performance and the vocals make it an achingly poignant track.
Wake me up when September endsGreen Day
The band Green Day, who sing this song, are from the United States, and the lyrics include the word “September.” In America, September marks the start of a new school year, and the music video for this song somehow evokes memories of the 9/11 terrorist attacks.
There are various ways to interpret it, but the song’s content is about a boy’s feelings for his deceased father.
FallJustin Bieber
We also say “Fall” for autumn in English, and how about this Justin Bieber song that uses that word in its title? The title means “to fall in love,” and somehow the vibe of the song feels autumn-like, doesn’t it? I also recommend translating the lyrics into Japanese as part of your English studies.
LoveLana Del Rey
This is a song by Lana Del Rey, a singer-songwriter from New York, USA.
It’s included on her 2017 album, Lust for Life.
The grand sound is beautiful—like an autumn breeze sweeping through.
It carries a message of cherishing the one you love.
I recommend it to anyone who’s in love right now.
Littlest ThingsLily Allen
Everything—the mood of the intro, the timbre of the piano, Lily Allen’s way of singing, and the content of the lyrics—is expressed so poignantly.
The title can be translated as “Just a Little Thing,” and precisely because of that, the nuances of you that resurface in everyday life feel all the more heartrending.