[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 Collection of Dark/Depressive Western Songs Middle Schoolers Should Listen To (1–10)
everything i wantedBillie Eilish
Released in November 2019, Billie Eilish’s work lays bare the loneliness and anxiety brought on by sudden success, a song steeped in deep darkness.
Sparked by a nightmare in which she jumped from the Golden Gate Bridge and no one seemed to care, it poignantly voices the emotional pain that comes with fame.
Yet at its core is the powerful bond between siblings: at the edge of despair, her brother Finneas vows, “As long as I’m here, no one can hurt you.” Whispered vocals, minimal piano, and a drifting, weightless atmosphere gently cradle her delicate state of mind.
Winner of Record of the Year at the 2021 Grammys, this piece reminds us how vital family support can be—and is a song that middle schoolers feeling lonely should especially hear.
pretend to like merenforshort
Singer-songwriter renforshort from Toronto, Canada.
Born in 2002, she has earned support from young people around the world by candidly singing about the anxieties and conflicts unique to adolescence.
Released in March 2025, this track portrays an earnest wish: “I want you to see the real me,” and “Even if it’s a lie, I want you to love me.” Its distorted guitar sound and raw vocals vividly express the pain of unrequited love and the wavering of self-esteem.
The anecdote that she rewrote the verse seven times also conveys how serious she is.
The impatience of feeling stuck in a one-way street, not knowing how the other person feels; the frustration of wanting validation but being unable to be honest—middle schoolers who’ve felt this way will surely find it deeply resonant.
American TeenagerEthel Cain
Ethel Cain is a singer-songwriter from Florida who has attracted attention for her Southern Gothic worldview.
Openly transgender, she depicts religious oppression and the darker sides of the American South with a distinctive musical style.
Featured on her debut album Preacher’s Daughter, released in May 2022, this song portrays the loneliness and despair lurking behind the American Dream through scenes like high school football and a neighbor’s brother who never returns from war.
The contrast between the exhilarating rock sound and the heavy message is striking, and it may resonate deeply with middle school students who feel anxious about the future.
I Love You, I’m SorryGracie Abrams
A quietly sung piece about the lingering feelings for that person we loved but broke up with—something everyone runs into sooner or later.
Gracie Abrams is a rising singer-songwriter known for opening on Taylor Swift’s tour, and this track, included on her second album The Secret of Us released in June 2024, became a global hit in no time.
The lyrics confess a contradictory feeling—“I love you, I’m sorry”—as she recognizes both the trouble she caused and her own weakness in being unable to let go.
It’s a portrait of complex emotions that many can relate to.
Whispered vocals over gentle guitar and piano tones tenderly embrace the pain deep in the heart.
For those who can’t recover from heartbreak or who haven’t sorted out their feelings for an ex, this song is sure to be one that stays close to you.
life, i’m over youZevia
Singer-songwriter Zevia gives voice to the complex emotions of adolescence.
In this track from the February 2022 album “we’re all sad here,” it portrays the despair felt at eighteen and the faint hope that something might change at nineteen.
The song conveys a heartfelt conflict of “wanting to stay but needing to leave,” along with a longing to be saved by someone.
With minimalist piano and synthesizers, the emotive vocals strike a deep chord.
It’s a song I especially recommend to junior high school students who feel anxious about the future and frustrated with their present selves.