Saddest Western Songs Ranking [2025]

Love Is a Losing GameAmy Winehouse99rank/position

Amy Winehouse – Love Is A Losing Game

This is an achingly poignant masterpiece by Amy Winehouse, the singer from England.

True to its title, “Love Is a Losing Game,” it sings of the futility of a love you know will never be rewarded, no matter how hard you try.

Even after giving everything, you’re left behind in the end, with a crushing sense of defeat and helplessness.

Anyone who’s worn themselves down in a barren, one-sided love will feel the sting of this hopeless situation all too well.

Her voice—deep and tinged with resignation—doesn’t console so much as it quietly stays beside the pain.

It’s a song that seeps into your heart on nights when you’re burdened with sorrow that has nowhere to go.

Overpass GraffitiEd Sheeran100rank/position

Ed Sheeran – Overpass Graffiti [Official Video]

Ed Sheeran is an artist who’s hugely popular in Japan as well.

Many people probably got to know him through his 2017 release, “Shape of You.” The song he released in October 2021, “Overpass Graffiti,” is a straightforward breakup track that portrays the feelings of a man who, after some time has passed since saying goodbye, still can’t forget his ex.

Combined with the bittersweet melody, it’s a masterpiece that’s been crafted into a deeply emotional work.