A wonderful classic

[2026] A roundup of dark Western songs I'd like middle schoolers to listen to

music writerKOH-1
Started working as a music writer as a side job while employed at a record shop, and for over 18 years I’ve contributed to music magazines, disc guide books, mooks, and web media. As a writer my main field is Western music, but as a listener for over 35 years, I always try to keep my curiosity alive with the motto “I like what I like.” I have experience playing in bands, where I was a bassist who handled songwriting and composition. Instruments I’ve played include bass, guitar, and piano. I began studying English in my mid-40s and continue to do so today.

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.

[2026] A Collection of Dark Western Songs for Middle Schoolers to Listen To (81–90)

Too Good At GoodbyesSam Smith

Sam Smith – Too Good At Goodbyes

Too Good At GoodbyesSam Smith

Autumn often makes us feel a little melancholic, so let’s listen to some wistful ballads.

Among recent ballads, this song by Sam Smith is especially recommended.

Just listening to it will make your heart ache.

His wonderful voice is a perfect match for long autumn nights.

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Rihanna ft. Mikky EkkoStay

Rihanna – Stay ft. Mikky Ekko

Rihanna ft. Mikky EkkoStay

Against the calmly mechanical, almost robot-like piano playing, not the upbeat Rihanna-style singing you often imagine, but a dignified voice emerging from the quiet is striking.

As the title suggests, the wish for someone to stay by your side is an eternal theme.

It’s a song I recommend to middle school students as well.

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RedTaylor Swift

Taylor Swift – Red (Live from New York City)

RedTaylor Swift

It’s a song that sings about memories with a former lover, comparing winter to a colorless season and autumn to a vivid crimson.

Their love was that kind of burning red.

Even after losing it, the song respects the self that once burned—so in a way, it feels positive.

It’s a perfect track for autumn.

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StayZedd, Alessia Cara

Zedd, Alessia Cara – Stay (Lyric Video)

StayZedd, Alessia Cara

Autumn is a season when the scenery is beautiful, with things like fall foliage.

“Stay,” which features such stunning landscapes in its viral video, is perfect for autumn.

Of course, the music is catchy too, and it became a huge hit, especially among young people.

The way the sound actually thins out in the chorus might be the secret to its Western pop vibe.

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even the nights are betterAir Supply

Air Supply – Even The Nights Are Better (Official Video)

even the nights are betterAir Supply

It’s a gentle song that really tugs at the heart on summer nights.

The lyrics feel like telling someone heartbroken from a breakup, “I’m always by your side; I’ll give you my love anytime.” It doesn’t mention summer explicitly, but for some reason, listening to it always makes me think of summer.

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