[2026] Recommended for junior high schoolers! A roundup of tearjerker Western songs

Sailor SongGigi Perez

Gigi Perez – Sailor Song (Official Music Video)

Released in July 2024, this work by Gigi Perez rose from a viral TikTok hit to worldwide success.

It’s an indie-folk ballad that portrays passionate feelings for a lover who resembles actress Anne Hathaway.

The lyrics tenderly capture the yearning for a fierce, sailor-like love and the poignant wish to meet in dreams.

Celebrated for its frank depiction of a romance between two women, the song topped the charts in the UK and Ireland.

It’s a track I recommend to middle schoolers who can relate to the deep feelings of loving someone and the pain of being apart.

ceilingsLizzy McAlpine

Lizzy McAlpine – ceilings (official video)

Singer-songwriter Lizzy McAlpine from Philadelphia has been gaining attention for her delicate sound that blends folk and indie pop.

This track from her album “Five Seconds Flat,” released in April 2022, tells a poignant story in which a blissful night spent with a lover turns out to have been only a dream.

The late reveal—“it wasn’t real”—captures the pain of heartbreak with striking realism and is sure to bring tears to your eyes.

The song went viral on TikTok and peaked at No.

54 on the Billboard Hot 100.

If you’re a middle schooler who can’t forget an ex, be sure to give it a listen.

would’ve been yousombr

sombr – would’ve been you (official visualizer)

Somber is a singer-songwriter from New York who achieved global breakthrough on TikTok.

The track he released in 2023 is a heartbreak song that mournfully explores the “what ifs”—if only that person had been there, maybe I could have been saved.

Its dreamy guitar tones and delicately layered sounds seep into your heart.

The song has surpassed 100 million streams on Spotify, capturing the hearts of many listeners.

It’s a piece that gently stays beside those who carry unspoken loneliness and regrets for a past that can’t be reclaimed.

In The StarsBenson Boone

Benson Boone – In The Stars (Official Music Video)

Singer-songwriter Benson Boone from Washington state rose to stardom via TikTok.

Released in April 2022, this work is a tribute ballad that expresses the deep sorrow of losing his beloved great-grandmother through beautiful metaphors of stars and morning scenes.

It begins with a simple, piano-driven accompaniment, and the chorus strikes the heart with soaring high notes.

Later included on the album Fireworks & Rollerblades, it reached the top 10 in countries such as the Netherlands and Norway.

It’s a song that can deeply resonate with middle schoolers grieving the loss of someone precious and grappling with an overwhelming sense of emptiness.

Empty BenchDavid Kushner

David Kushner – Empty Bench (Official Music Video)

David Kushner, an American singer-songwriter who has drawn worldwide attention thanks to his success on TikTok, released a ballad in December 2024 for the Christmas season that portrays a farewell to a loved one.

With his resonant baritone and introspective lyrics, he layers feelings for someone he will never see again onto the symbol of an empty bench, quietly retracing memories of places they once shared.

The restrained arrangement, centered on piano and strings, gently wraps the sorrowful, prayer-like emotion.

Give it a listen when you want to be reminded of how precious time with loved ones and friends truly is.

this is what losing someone feels likeJVKE

this is what losing someone feels like (official video)

Jake, a young singer-songwriter who shot to global fame on TikTok, became a familiar name among Japanese music fans after his 2022 hit “golden hour” took the world by storm.

Released in March 2023, this work is a ballad that quietly portrays the regret and pain of losing someone dear.

The protagonist’s feelings—agonizing over small everyday choices like “If only we’d had that coffee together” or “If only I’d picked up the phone”—are poured out over a gentle piano melody.

The delicate emotions of trying to accept the irreversibility of loss may well bring you to tears.

It’s a song that gently stays by your side when you’ve experienced heartbreak or parting.

drivers licenseOlivia Rodrigo

Olivia Rodrigo – drivers license (Official Video)

Although it was released in January 2021, this song remains a classic that still captivates many hearts.

Born in 2003, Olivia Rodrigo is also active as an actress in a Disney TV series, but this lead single from her debut album SOUR catapulted her into stardom as a singer-songwriter.

The lyrics depict a protagonist who has just gotten her driver’s license, driving alone at night with a lost love on her mind, powerfully conveying the pain of a vanished, once-promised future and the struggle with feelings that won’t fade.

The way it elevates complex emotions—jealousy toward an ex’s new girlfriend and doubts about oneself—from a simple, piano-based arrangement into a dramatic climax is masterful, making its eight-week run at No.

1 on the Billboard Hot 100 entirely convincing.

It’s a perfect song for anyone who wants to empathize with the pain of heartbreak, or to sink into melancholy during a solitary drive.