Saddest Western Songs Ranking [2025]

BeautifulChristina Aguilera78rank/position

Christina Aguilera – Beautiful (Official HD Video)

A song written by Linda Perry.

It is also known as a track embraced by the gay community.

Released as a single by Christina Aguilera in 2002, the song won the Grammy Award for Best Pop Vocal Performance.

DeucesChris Brown ft. Tyga, Kevin McCall79rank/position

Chris Brown – Deuces (Official HD Video) ft. Tyga, Kevin McCall

It’s a laid-back, downtempo R&B ballad featuring Chris Brown’s smooth vocals.

The song drew attention amid speculation that it might be about his past relationship with his ex-girlfriend, the singer Rihanna.

Out of TimeThe Weeknd80rank/position

The Weeknd – Out of Time (Official Video)

Hailing from Canada and transcending the boundaries of contemporary R&B to stand as a top star in the world of popular music, The Weeknd is known for crafting many songs inspired by his own romantic experiences.

His ability to transform even messages steeped in lingering feelings for an ex into mysterious, beautiful masterpieces is nothing short of remarkable.

Among his sad yet beautiful breakup songs, this time we’ll focus on “Out of Time,” released in 2022.

Featured on his fifth studio album, Dawn FM, it became a hot topic for sampling “MIDNIGHT PRETENDERS,” composed by Tetsurō Oda and included on Tomoko Aran’s 1983 album Fuyū Kūkan—a classic of Japanese city pop.

While the track is a sleek, urban pop song that’s a pleasure to listen to, the lyrics, as the title suggests, express thoughts for a former lover that arrive too late, no matter how much one regrets.

Some listeners may find it so relatable that it’s almost painful.

One Right NowPost Malone, The Weeknd81rank/position

Post Malone, The Weeknd – One Right Now (Official Music Video)

Released in November 2021, One Right Now is a collaboration between Post Malone and The Weeknd, two artists who command enormous support in the contemporary pop scene.

Built on a sleek synth-pop track that reflects a post-2020s trend, the interplay of Malone’s and The Weeknd’s emotional vocals and melodies creates a stunning contrast—truly exquisite.

Lyrically, however, it seems to be a message to an ex whose infidelity likely caused the breakup, conveying a sense of saying goodbye to the past relationship and already having someone new.

That said, depending on how you interpret it, it can also read as the poignant lament of a man still full of lingering attachment, unable to fully move on.

With that in mind—perhaps reading too much into it—the music video, in which the two stage a brutal shootout, feels oddly suggestive as well.

Closing TimeSemisonic82rank/position

Semisonic – Closing Time (Official Music Video)

A song by the American rock band Semisonic that was also nominated for the Grammy Award for Best Rock Song in 1999.

It is about customers leaving a bar after closing time.

The track has been used in many films and television series.

Kill BillSZA83rank/position

SZA – Kill Bill (Official Video)

SZA’s “Kill Bill” achieved the remarkable feat of holding the No.

1 spot for multiple weeks, leaving a vivid mark on the music scene.

The song delicately yet boldly captures the complex emotions after a breakup.

Inspired by the film, SZA’s lyricism shines as she expresses lingering feelings for a past lover and a fiery urge for revenge.

Beyond its deeply moving content, the modern synth-driven production highlights her delicate vocals.

“Kill Bill” not only dominated the charts but also resonated widely as a breakup anthem.

Hold Me While You WaitLewis Capaldi84rank/position

Lewis Capaldi – Hold Me While You Wait (Interlude Session)

Lewis Capaldi is a singer-songwriter who enjoys global popularity not only in his native Scotland but around the world.

He is highly acclaimed for his rich expressiveness and resonant baritone voice.

One of his well-known hits, Hold Me While You Wait, was released in 2019 and gained popularity for its poignant, catchy melody and lyrics that portray a man hoping to rekindle a relationship.

Be sure to check it out.