Cyndi Lauper Popular Song Rankings [2026]

When You Were MineCyndi Lauper41rank/position

Cyndi Lauper – 1985 When You Were Mine (Live at American Music Award)

The intro gives quite a pop impression.

From the verse, it’s a very cheerful number.

Including the pre-chorus, the chorus flows in naturally, and the whole song progresses that way.

I think this is the album where they started to become popular, so it’s worth checking out.

You Don’t KnowCyndi Lauper42rank/position

Cyndi Lauper – You Don’t Know

It is included on the album “Sisters of Avalon.” With its upbeat rhythm and the memorable phrase featured in the title, it’s a track that sticks in your ears.

The lyrics, which seem to interrogate someone over a relatively gentle melody, feel as if they’re questioning me, which gives me a jolt.

Kinky Boots: Lola’s World (The BEST Lola)Cyndi Lauper43rank/position

Callum Francis – The BEST Lola in Kinky Boots

Kinky Boots, the Broadway musical etched in many people’s memories as one of Haruma Miura’s signature works.

The story depicts a men’s shoe factory on the brink of bankruptcy turning its business around after meeting the drag queen, Lola.

This piece is The Land of Lola, used during Lola’s entrance scene.

It’s a song that conveys the glamour and strength of drag queens.

It’s an impressive track that blends the hallmarks of Cindy Lauper—who could be called a master craftsperson of pop music—with elements of gospel.

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A Night To RememberCyndi Lauper44rank/position

Cyndi Lauper – A Night To Remember

This is a song that struck me as having a very mature way of thinking.

The lyrics convey the struggles of a grown woman who still likes him but neither says it nor tries to appeal to him, choosing instead to worry and think it through on her own.

I think it’s a song I’d want adult women to listen to.

Heartaches By The NumberCyndi Lauper45rank/position

Cyndi Lauper – Heartaches By The Number – Live Performance

This is Cyndi Lauper’s cover of a popular country song written by Harlan Howard and released in 1959.

Cyndi’s vocals blend perfectly with the comforting, uniquely country atmosphere.

Included on the studio album Detour.