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

teenage dreamOlivia Rodrigo

Olivia Rodrigo – teenage dream (Official Lyric Video)

For middle schoolers who feel anxious that “I should be growing up already, but maybe the best part of me is already gone,” I’d like to recommend this track from Olivia Rodrigo’s second album, GUTS.

Released in September 2023, it’s an introspective piano ballad she wrote just before turning 19, after years of being told she was “mature for her age.” It quietly sings of the hopes and fears of growing up, and the guilt of not becoming your ideal self, offering deep comfort to students who feel rushed or worried about the future.

life, i’m over youZevia

Zevia – life, i’m over you (Official Lyric Video)

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.

pretend to like merenforshort

renforshort – pretend to like me (official music video)

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.

BAD FEELINGSBLÜ EYES

BLÜ EYES – BAD FEELINGS (Official Music Video)

This song carefully portrays the pain of suppressing emotions and the inner turmoil of feeling pressured to stay positive.

Katie Stamp, also known as Blue Eyes, is a singer-songwriter gaining attention in the indie pop scene, and she released the album “The Last Songs I’ll Write About You” in May 2023.

This piece was released in August 2025 and was created from the perspective of what she would tell her 10-year-old self about emotions.

It teaches the importance of truly feeling your feelings instead of forcing a smile when you’re sad.

If you’re a middle schooler struggling with friendships or your future, be sure to check out the Japanese translation as well.

Alley RoseConan Gray

Conan Gray – Alley Rose (Official Lyric Video)

Conan Gray, whose father is Irish American and mother is Japanese, also spent part of his childhood living in Hiroshima, and his later years in Texas shaped his musical style.

This track from his April 2024 album Found Heaven is a piano rock ballad reminiscent of Elton John in the ’80s.

Written about his experience of being broken up with via text while in London, Gray himself calls it his “first love song,” and it’s a warm, heartfelt piece.

If you’re a middle schooler nursing a broken heart, give it a listen.

Won’t OverdoseLil Xan

Lil Xan – Won’t Overdose (Official Video)

Lil Xan, who emerged from the SoundCloud scene and became known as a torchbearer of emo rap, takes his stage name from the anti-anxiety drug Xanax and has candidly expressed his own experiences with substance dependency.

In this track, released in September 2024, he parts ways with that past, declaring a firm resolve to “never overdose again.” It’s a highly message-driven work aimed at a generation seeking recovery from addiction, featuring introspective lyrics laid over a dark trap beat.

Teaming up with producer Kinfolk Jon, they’ve crafted an airy, floating sound.

It’s a song that will likely resonate deeply with middle schoolers buffeted by today’s ailing society and the age of social media, as well as with anyone grappling with loneliness or a sense of emptiness.

PsychoMaisie Peters

Maisie Peters – Psycho [Official Music Video]

Maisie Peters is a singer-songwriter from England.

Signed to Ed Sheeran’s label, she captivates young listeners with emotionally charged pop songs.

Featured on her debut album, “You Signed Up for This,” this track depicts a toxic relationship with an ex who repeatedly gaslights and cheats.

While he calls her a “psycho,” the irony is that he’s the one who is self-centered and cold, a theme delivered over a catchy pop sound.

Despite its bright melody, the song tackles heavy subject matter.

As Peters herself has said, “everyone in the world can relate to people who hurt others and feel nothing,” making it a piece that will deeply resonate with middle schoolers who have experienced unfair treatment.