Songs That Make You Cry: Heart-Wrenching Western Music—from Timeless Classics to the Newest Hits
There are times when, instead of listening to music to get pumped up or fired up, you deliberately want to listen to poignant or slightly sad songs and have a good cry alone, right?
Upbeat tracks that give you a push are great, but in this article we’ve researched and selected timeless, heart-wrenching English-language songs that empathize with listeners’ feelings, both old and new.
From classic standards to recent hits and the latest buzzworthy tracks, we’re bringing you a genre-crossing selection.
Try listening in whatever setting makes you feel most at ease—whether that’s in your bedroom or on a drive!
- Top Tearjerker Western Songs Ranking [2026]
- Western songs about saying “goodbye” — perfect for bereavement or a departed lover
- When you’re hurting and feel like you want to disappear… timeless Western songs to listen to at times like these
- Hidden gems of tear-jerking Western songs. Recommended popular tracks.
- [2026] Moving Western songs that touch the heart: A roundup of recommended classics
- Top Cry-Inducing Western Songs Ranking [2026]
- Beautiful, lovely Western music. A roundup of recommended classic songs.
- Top 2026 Rankings of Melancholic Western Songs
- A Collection of Heart-Touching Western Ballads — From Classics to the Newest Hits
- Really dark... Classic Western songs | So dark that it may trigger depression—proceed with caution!
- Western songs used in commercials — tear-jerking classics and popular tracks
- A collection of emotionally resonant dark-themed Western songs—tracks with lyrics that deeply echo in the heart
- Emotional Western Music Special | Handpicked from All Generations
Tearjerkers! Heart-wrenching Western Songs — From Timeless Classics to the Newest Hits — (121–130)
PerfectSimple Plan
It’s a song that expresses the complicated feelings of adolescence—knowing I’m not perfect and feeling sorry toward my parents.
I think the reason Simple Plan resonates so well with teenagers is that they directly capture these uniquely adolescent emotions in their music.
I discovered this song when I was in middle school and listened to it all the time.
This Is The Sound OfSnow Patrol
A rock band that Scotland is proud of, Snow Patrol have released their first single in seven years.
Interweaving poetic, emotional lyrics with their signature melodic sound, the track is said to center on a long-distance relationship and truly resonates with listeners.
Speaking of the band, “Chasing Cars” from their 2005 album Eyes Open is known as the most-played song on UK radio in the 21st century.
With its romantic atmosphere, this new song is perfect for moments when you want to reminisce about a lover or think of someone special.
Why not give it a listen on a calm, quiet night?
LostSoccer Mommy
Released in June 2024, the song with a hauntingly poignant melody comes from American singer-songwriter Soccer Mommy, who performs indie rock influenced by pop music.
Blending emotionally rich lyrics with delicate acoustic guitar, orchestral strings, and natural birdsong, the track showcases her signature musicality to the fullest.
The lyrics revolve around regret and longing for lost relationships and missed opportunities.
They delve deeply into the protagonist’s inner world—lamenting not fully appreciating a past relationship and yearning for another chance amid feelings of alienation and an incomprehensible situation.
Following the album “Sometimes, Forever,” this song opens up a new frontier for her, making it a perfect choice for quiet nights alone or moments of introspection.
Casimir Pulaski DaySufjan Stevens
A song included on the 2005 concept album Illinois.
The title, Casimir Pulaski Day, refers to an Illinois state holiday held on the first Monday of March each year, honoring Casimir Pulaski, a Polish cavalry officer who fought in the American Revolutionary War.
Tearjerkers! Heartbreaking Songs in Western Music — From Timeless Classics to the Newest Hits — (131–140)
If I Were To DieWinona Oak
The song released in February 2024 by Swedish artist Winona Oak is a poignant love ballad that portrays the fear of losing someone you love and the courage to choose love anyway.
Winona’s clear, airy vocals delicately capture the vulnerability and beauty of falling in love.
This track was unveiled as a single ahead of the EP “Void,” scheduled for release on May 3, 2024.
Reflecting a difficult period Winona experienced, the piece is sure to resonate deeply with listeners.
It’s a recommended listen for anyone who, while imagining a possible farewell to a loved one, still cherishes the precious time spent together.
Damn You For Breaking My HeartCaitlyn Smith
If you love grand, sweeping songs, I recommend “Damn You For Breaking My Heart.” The verses are relatively calm, but once the chorus hits, it bursts into a powerful, fast-paced, expansive melody.
The lyrics are quite dark and heavy, so have a handkerchief ready when you look them up…
Wish You Were HereAvril Lavigne
This moving song comes from Canadian singer-songwriter Avril Lavigne.
It expresses the bittersweet feelings that follow the loss of a loved one, conveyed through her uniquely powerful vocals.
Included on the album Goodbye Lullaby, it was released as a single in September 2011 and reached No.
65 on the Billboard Hot 100.
It’s recommended for those who have experienced heartbreak or farewells, or who want to reflect on time spent with someone special.
You’re sure to relate to Avril’s delicate emotional expression.
In November 2011, she also delivered a live performance on Good Morning America that resonated deeply with many viewers.