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[2025] Recommended popular melancholic summer classics in Western music

Party anthems that hype up the hot summer are great, but there are probably many of you who also want to chill at dusk with bittersweet melodies and sounds.

In this article, we introduce popular Western hits and recommended classics under the theme of “Bittersweet Summer Masterpieces.”

The first half highlights the latest releases and recent favorites, while the latter half lines up a host of timeless classics.

From laid-back numbers to upbeat tracks whose melodies and lyrics are achingly poignant, enjoy a wide variety of summer songs!

[2025] Best Heartbreaking Summer Western Music: Recommended Popular Songs (131–140)

Hopelessly Devoted To YouOlivia Newton-John

Mariah Carey, Olivia Newton-John – Hopelessly Devoted to You (from Around the World)
Hopelessly Devoted To YouOlivia Newton-John

Olivia Newton-John, a female singer from Australia who has many fans in Japan.

The love ballad she performed in the film Grease, in which she starred alongside John Travolta, is known in Japan by the title “Aisuredo Kanashi” (“I Love You, But It’s Sad”).

In this song, where Olivia sings, “I love you so much I can’t help myself,” the bittersweet feeling is turned up to 100%.

DriveThe Cars

The Cars – Drive (Official Music Video)
DriveThe Cars

The Cars are a rock band from the United States.

As a new wave band, they enjoyed popularity in the 1980s.

Among their works—many of which have a strong rhythmic drive—“Drive” stands out as one of their finest slow ballads.

It was released in 1984, and its wistful melody, evocative of the fading summer, is especially captivating.

La Isla BonitaMadonna

Madonna – La Isla Bonita (Official Video)
La Isla BonitaMadonna

A single released in 1987 by the charismatic American singer Madonna.

The track is included on her 1986 album True Blue.

The title “La Isla Bonita” is Spanish for “The Beautiful Island,” and the San Pedro mentioned in the song refers to a city on a coral island in the Caribbean.

It’s a dreamy, Spanish-flavored piece that evokes the feel of summer.

In conclusion

I introduced some bittersweet Western songs that you’ll want to listen to in the summer.

Sound-wise, a lot of them tend to feel cool and soothing, or gently mellow.

Listening to songs like these can make you feel the end of summer, or bring back memories of a summer fling and other moments that linger in your heart.

I hope you find a bittersweet summer song in English that fits your heart.