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

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.

It’ll Be OkayShawn Mendes

Shawn Mendes – It’ll Be Okay

A piano ballad released in December 2021.

Canadian singer-songwriter Shawn Mendes delivers a quiet portrayal of the pain and acceptance of facing a breakup.

It begins by questioning the end of a relationship, then offers a vow to keep loving the other person—a message that resonates, wrapped in organ-like synths and strings.

When you’ve parted ways with someone important, whether in friendship or romance, there are moments when you want to tell yourself, “It’s going to be okay.” This song gently stays by your side in those moments.

The music video, set against nighttime views of his hometown Toronto and snowy scenes, leaves a strong impression with its world that balances loneliness and warmth.

Recommended for those going through heartbreak, as well as middle schoolers struggling with a relationship.