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[2025] A Collection of Dark Western Songs Middle Schoolers Should Hear

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.

[2025] A Compilation of Dark Western Songs Middle Schoolers Should Listen To (91–100)

I keep forgettingMichael McDonald

Michael McDonald – I Keep Forgettin’
I keep forgettingMichael McDonald

It’s a song that captures the feelings of a man whose love ended at the same time summer did.

A “summer fling” is a common phrase—the heat of summer lifts your spirits, and as the season draws to a close, those feelings cool, leaving a bittersweet aftertaste.

When you come back to your senses at summer’s end, it’s almost painfully perfect to listen to.

Obladi ObladaThe Beatles

The Beatles – Ob-La-Di, Ob-La-Da
Obladi ObladaThe Beatles

It’s the perfect song for riding along the coastline in a minibus, gazing at the blue sea, and singing together with a big group.

For young people, it’s an ultra-positive song that says life is still long and a bright future lies ahead.

I think everyone’s heard it at least once, and it’s a classic that can lift your spirits even when you’re feeling down.

[2025] A roundup of dark Western songs we want middle schoolers to listen to (101–110)

Girls Like YouMaroon 5 ft. Cardi B

Maroon 5 – Girls Like You ft. Cardi B (Official Music Video)
Girls Like YouMaroon 5 ft. Cardi B

In the fall, when it’s easy to feel nostalgic, you tend to want to listen to songs that bring back memories.

This Maroon 5 track is a love song that tells a story while looking back on the past.

The lyrics portray a bittersweet heartbreak, so give it a listen when you’re in the mood for something wistful.

WonderwallOasis

Oasis – Wonderwall (Official Video)
WonderwallOasis

When it comes to Oasis, this is the song! It’s an ultra-popular track loved by many.

The laid-back acoustic guitar in the intro is striking and really suits a scene of autumn leaves dancing along a promenade.

How about using it as background music for a walk while reflecting on the path you’ve taken?

Gust of WindPharrell Williams

Pharrell Williams – Gust of Wind (Video)
Gust of WindPharrell Williams

It was included on Pharrell Williams’s second album, G I R L, and was later released as the tenth single.

It’s also known for featuring Daft Punk.

The song’s subtly robotic, digital vibe feels somewhat autumnal.

It’s one of those tracks you’ll want to tell your friends about!

Don’t Let Me DownThe Chainsmokers ft. Daya

The Chainsmokers – Don’t Let Me Down (Official Video) ft. Daya
Don't Let Me DownThe Chainsmokers ft. Daya

Speaking of autumn, it’s a comfortable season, so many middle schoolers probably go out with friends.

This is the song I want you to listen to with your friends on those outings.

In the music video, the two members of The Chainsmokers are shown driving.

Don’t Be So Hard On YourselfJess Glynne

Jess Glynne – Don’t Be So Hard On Yourself [Official Video]
Don't Be So Hard On YourselfJess Glynne

When it comes to Western songs that are perfect as cheer songs for summer high school baseball, how about this track by Jess Glynne? Its message of “Don’t be so hard on yourself!” is a perfect cheer for high school ballplayers who aren’t afraid of mistakes or defeat.