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 Compilation of Dark/Depressive Western Songs Middle Schoolers Should Listen To (71–80)

TroublemakerOlly Murs ft. Flo Rida

Olly Murs – Troublemaker ft. Flo Rida

TroublemakerOlly Murs ft. Flo Rida

In this upbeat, catchy song, he sings about calling the girl who stirs up his heart a troublemaker.

Of course, that’s really his feelings in reverse, but that kind of twisted, can’t-look-at-things-straight-on attitude is pretty common in love, isn’t it? Don’t you middle schoolers have a lot of moments like that too?

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You know meRobbie Williams

Robbie Williams | You Know Me (Official Video)

You know meRobbie Williams

It’s a song about regrets overflowing without end, and personally, I even feel like it’s almost negative promotion.

Because it’s an ex who I felt truly knew my real self, it’s hard to fully move on.

That’s the gist of the lyrics, but the song itself has a somewhat light, pop feel and is easy to listen to.

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Be With YouRoger Taylor

Roger Taylor – Be With You

Be With YouRoger Taylor

First off, the plaintive, weeping guitar in the intro is heartbreaking—it really evokes the deepening of autumn.

By the time you’re in middle school, people’s musical tastes start to diverge, and some will come to love this kind of adult, understated sophistication.

Definitely try listening to it while taking a walk through fallen leaves.

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Don’t Tell MeRuel

Ruel • Don’t Tell Me (Official Audio)

Don't Tell MeRuel

When this song by Ruel came out, he was just 14 years old, and even Elton John—after hearing it—said, “I’m blown away!” Indeed, the maturity and vocal prowess in his voice are remarkable.

In Japan, that’s around middle-school age, right? This track makes it clear that it’s never too early to start something.

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No Ordinary LoveSade

Sade – No Ordinary Love – Official – 1992

No Ordinary LoveSade

As shown in the music video, the song has an atmosphere like being underwater, making it feel like a private world that shuts out the outside.

That kind of musical worldview may be what strengthens the persuasiveness of this grand love song about giving all my love to you.

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