[2026] Best melancholic summer classics in Western music: recommended popular songs
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!
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[2026] Best bittersweet summer classics in Western music: recommended popular songs (131–140)
SongbirdKenny G
Kenny G is a saxophone player from the United States.
Active in the fusion genre, he released the album Duotones in 1987, which became his first work to reach the top 10 on the U.S.
charts.
Included on that album is Songbird.
Distinguished by its delicate sensibility, the piece is widely beloved in Japan as well.
Never Really Loved MeKygo, Dean Lewis
Kygo, a singer who represents Norway and is also known worldwide as a trackmaker, collaborated with Australian singer Dean Lewis on “Never Really Loved Me.” Kygo hasn’t created many love songs in the past.
This time, however, he brought in Dean Lewis—renowned for his love songs—as the vocalist, taking on a style he hasn’t tried before.
Pay attention to the poignant lyrics that make you reflect on the meaning of love.
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 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
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.