Cyndi Lauper Songs Ranked

Cynthia Ann Stephanie Lauper (born June 22, 1953) is an American singer, songwriter, actress, and activist. Her career has spanned over 40 years. Her album She’s So Unusual (1983) was the first debut album by a female artist to achieve four top-five hits on the Billboard Hot 100—” Girls Just Want to Have Fun”, “Time After Time”, “She Bop”, and “All Through the Night”—and earned Lauper the Best New Artist award at the 27th Grammy Awards in 1985. Her success continued with the soundtrack for the motion picture The Goonies and her second record True Colors (1986). This album included the number one single “True Colors” and “Change of Heart”, which peaked at number three. Lauper has been celebrated for her humanitarian work, particularly as an advocate for LGBT rights in the United States. Her charitable efforts were acknowledged in 2013 when she was invited as a special guest to attend U.S. President Barack Obama’s second-term inauguration. Here are all of Cyndi Lauper songs ranked.

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20. Heading West (A Night to Remember, 1989)

“Amazing how much my tastes have changed as of late. Cyndi Lauper has still got it! Some catchy stuff here. Not quite as good as her first two albums, but she’s still as weird as ever and is fun to listen to. “

19. Sisters of Avalon (Sisters of Avalon, 1996)

“A very different outing for Cyndi, Sisters Of Avalon is highly eclectic, but somehow manages to hold together. As usual, her incredible voice takes center stage, but the style and  production are quite varied and interesting.”

18. Yeah Yeah (She’s So Unusual, 1983)

“”Yeah Yeah” is downright grotesque (the fuck’s with the dollar-store carnival organ?), when it comes down to it this is pop music for people who look down on music: pure gimmick, yet couched in an over-arching jokey kookiness that never fails to lead snobs along like donkeys toward a dangling carrot, topped with an unpleasant dash of affected feminine anemia – or alternately, submissiveness – that makes dudes who don’t really listen to women feel good about themselves for all the wrong reasons.”

17. Who Let in the Rain (Hat Full of Stars, 1993)

“Although I have a copy of Cyndi Lauper’s brillant 1993 release “Hat Full Of Stars”, I just had to buy “Who Let In The Rain” single, as it’s one of the greatest ballads in the world. Melody, arrangement, Lauper’s voice-everything is perfect here! Definitely one of my TOP 5 favourite Cyndi Lauper songs ever!”

See more: Cyndi Lauper Albums Ranked

16. A Night to Remember (A Night to Remember, 1989)

“Probably her greatest break up song. Such feeling and emotion went into this and the lyrics really tell how she feels.”

15. Unconditional Love (A Night to Remember, 1989)

“Totally underrated and unknown. Had this been released as the second single for this album, it would have been a huge hit.”

14. Into the Nightlife (Bring Ya to the Brink, 2008)

“To me, this song represented a new evolution in her sound and her success expanding into a new era. This song hit #1 on the Billboard Dance chart, proving that she was still relevant on today’s music scene. A great dance song.”

13. Hole in My Heart (All the Way to China) (Japanese Singles Collection – Greatest Hits, 2019)

“Very nice song and a brilliant performance by Cyndi Amazing and fun song! I loved her in Vibes! and I can’t listen to this song enough!”

12. What’s Going On (True Colors, 1986)

“The musicality of this song is brilliant. Her voice is perfect for Gaye’s song. She hit the top 20 with this, and the video was in the MTV top 20 countdown for weeks. It is a gorgeous production.”

11. I Drove All Night (A Night to Remember, 1989)

“I think this song is the best in her songs.. in this song is her longest note.. and rarest voice… I like Celine’s performance but I think Cindy’s performance of this song is the best… I like Cyndi’s rare, strong, deep, and wonderful voice..”

10. I’m Gonna Be Strong (Twelve Deadly Cyns…and Then Some, 1994)

“Vocally, this is one of her most amazing songs. It is powerful and emotional. Whether listening to the recording or a live version, it is always impressive. I think that a lot of people just don’t know about it.”

9. When You Were Mine (She’s So Unusual, 1983)

“When You Were Mine” is a Prince’s song but Cyndi’s version is much better. It’s a synths driven pop/rock number. In the middle of the song Cyndi hits this high note and it sounds incredible. Pure 80’s magic!”

8. Money Changes Everything (She’s So Unusual, 1983)

“Money Changes Everything” was last official single from “She’s So Unusual” album. Although it didn’t repeat success of previous four singles (it stalled at #26 on Billboard charts), I must admit it’s one of the best songs in Cyndi’s career. It’s a powerful, rocking 80’s song that has everything to be called an instant hit! Live version of this song is even better because shows how great performer Cyndi is and how powerful her voice really is.”

7. Change of Heart (True Colors, 1986)

“The lyrics are straight from the cliche factory (“would be”/”could be” gets used right out of the gate), and the music seems somehow busy AND thin. Like nobody played a melody, and they tossed in a lot of percussion and noises to distract you from noticing.”

See more: Ellie Goulding Albums Ranked

6. The Goonies ‘R’ Good Enough (The Goonies: Original Motion Picture Soundtrack, 1985)

“I can’t get enough of this song! Even if it is a song made for a movie, it is great! I love this song! It’s so catchy and very Goonie! Never say die!”

5. She Bop (She’s So Unusual, 1983)

“This song – She Bop – is but one of many so-called “bean-flicking anthems” of that period. Its carefree rhythm and lyrical flourishes speak to a different era, one where people found their own way to pleasure themselves – often at the risk of arrest and occasionally quite lengthy jail terms for repeat offenders!”

4. True Colors (True Colors, 1986)

“True Colors” does demonstrate some genuine craft: the gentle atmosphere and the cresting melody do offer the listener a lovely lilt effective for inducing sleep. Moreover, “True Colors” did have a seismic impact upon the LGBT community, providing a gentler pop anthem than their previous anthems, which tended to lie more on the bombastic side.”

3. Time After Time (She’s So Unusual, 1983)

“Time After Time” is a very very good song, it’s a ballad done by a punky pop princess but manages to sound sweet, and sincere even though it’s being sung by a girl that most people wouldn’t let into their house. The most beautiful part of “Time After Time” is its uncertainty. On its surface, the song is an expression of devotion: “I will be waiting time after time.” However, the meaning of the title adds a delightful bit of uncertainty. “Time After Time” could be a creative way of saying “forever” or “every time,” or it could be a more fatalistic expression of romantic entrapment and frustration.”

2. All Through the Night (She’s So Unusual, 1983)

“”All Through the Night”, though, is one of the originals.  Emerging from a great sequencer track, Lauper sings one of the sweetest and most heartbreaking love ballads ever.  And, behind it, you have not just synths but an actual band backing her up.  Male, female, any orientation – you find yourself singing along with this any time it comes on the radio. “

1. Girls Just Want to Have Fun (She’s So Unusual, 1983)

“It’s impossible to tell what’s Cyndi Lauper’s best song because all of her songs are incredible. Best singer of all time, music wouldn’t be the same without her. Girls Just Want to Have Fun is definitely one of my favorite songs by Cyndi Lauper, truly awesome in all ways.”