The 23 Greatest Cyndi Lauper Songs Of All Time, Ranked

We listen to these tracks time after time.

Not only is Cyndi Lauper one of the LGBT community’s most public allies, she’s an amazing singer-songwriter with a resume that spans four decades and a stack of hit songs. (Not to mention a Tony for Kinky Boots.)

Below, we salute Cyndi’s illustrious career with a look at her greatest songs. Did we miss one of your faves? Shout out in the comment section below.

Cyndi Lauper will honored at Logo Trailblazer Honors, airing June 23 at 9pm on Logo and VH1.

  1. “My First Night Without You” (1989)

    Cyndi’s third album, A Night To Remember, wasn’t a huge success, but there were some hidden gems: In addition to “I Drove All Night,” there’s “Heading West,” “I Don’t Want To Be Your Friend,” and the second single, “My First Night Without You,” which showcases her impassioned vocals.

  2. “Boy Blue” (1987)

    The fourth single from True Colors, “Boy Blue” packs a lot of heart: Cyndi wrote it about a friend who died from AIDS, and she donated all the proceeds to HIV/AIDS charities.

  3. “The Ballad of Cleo and Joe” (1997)

    This is a story of Joe, better known at night as drag queen Cleo. Fun fact: Cyndi was nine months pregnant when the video was filmed, and made inspired use of her belly.

  4. “Into the Nightlife” (2008)

    From Bring Ya to the Brink, “Into the Nightlife” became Cyndi’s first Number One on the dance chart since “Girls Just Wanna Have Fun.” It’s packed with infectious beats and Cyndi at her most seductive.

  5. “At Last” (2003)

    At Last, Cyndi’s 2003 album of standards, was her highest-charting (and best-selling) album since A Night To Remember. It found Cyndi in fine form on classics like “La Vie en Rose” and “If You Go Away,” but the title track always makes our heart melt.

  6. “The End of the World” (2016)

    Cyndi’s 2016 album, Detour, explored her country roots—and while “End of the World” is one of the record’s quieter ballads, its piercing lyrics will make your heart ache.

  7. “I’ll Kiss You” (1983)

    Cyndi’s punk-pop vibe was in full effect in this track off her debut album, She’s So Unusual. Breathless, angsty and hypnotically repetitive, it’s the ultimate shower-screamer.

  8. “Change of Heart” (1986)

    The second single off True Colors, “Change of Heart” features the invaluable assistance of Nile Rodgers on guitar and the Bangles on backing vocals.

  9. “You Don’t Know” (1997)

    The first single from Sisters Of Avalon, “You Don’t Know” takes on politicians who blindly follow orders. “Don’t shove that bullshit down my throat.” Trump administration, you hear that?

  10. “I’m Gonna Be Strong” (1994)

    For her 1994 greatest hits collection, Cyndi went back to the beginning and re-recorded this track, originally performed by her group Blue Angel. The memorable last note is just as powerful as it was in 1980.

  11. “What’s Going On” (1987)

    It takes confidence to cover Marvin Gaye, but Cyndi’s emotional retelling of the activist classic is sincere and endearing. Listen and weep.

  12. “Money Changes Everything” (1983)

    Cyndi kicked off She’s So Unusual with this cover of an underground classic by the Brains about how money can ruin a relationship. She later recorded an acoustic version with Taking Back Sunday’s Adam Lazzara for 2005’s The Body Acoustic. It’s a great reworking, but the plugged-in version is our favorite.

  13. “I Drove All Night” (1989)

    Roy Orbison recorded “I Drove All Night” around the same time, but Cyndi’s version was released first and landed on the Top 10.

  14. “Who Let In the Rain” (1993)

    The first single from Hat Full of Stars, it failed to even chart on the Hot 100, and the album peaked at a dismal #112. Both results were undeserved.

  15. “Shine” (2004)

    “Shine,” from Cyndi’s eponymous eighth album, combines belting vocals with an anthem melody. “When it’s said and done, What you need will come.” Cyndi sings, we listen.

  16. “Sally’s Pigeons” (1993)

    Many tracks on Hat Full of Stars tackled social issues, including this one (co-written by Mary Chapin Carpenter) about teen pregnancy and back-alley abortions. The a capella opening grips you and never lets go. (Fun fact: The music video features a then-unknown Julia Stiles.

  17. “She Bop” (1983)

    Cyndi’s ode to self-pleasure earned her a spot on PMRC’s “Filthy 15” list, and is the only Top 10 song to give a shoutout to a gay porn magazine. (“Well, I see him every night in tight blue jeans/In the pages of a Blueboy magazine.”)

  18. “The Goonies R Good Enough” (1985)

    Before beginning on her second album, Cyndi contributed two songs to the soundtrack of The Goonies: “What A Thrill” and our favorite,”The Goonies R Good Enough.” For some reason, Cyndi rarely performs either, and has even neglected to include them on many of her compilations.

  19. “Hole In My Heart” (1988)

    Her most underrated single, “Hole In My Heart” failed on the charts and caused the postponement of Cyndi’s third album. Like “Goonies,” “Hole In My Heart” became another song rarely heard in concert or featured on compilations until Cyndi started performing it on the 2007 True Colors Tour, nearly 20 years after its release.

  20. “All Through the Night” (1983)

    The debut smash “All Through the Night” never received the attention and adoration it warranted. Gorgeous and melancholy, it’s the greatest buried treasure of all Cyndi’s Top 10 hits.

  21. “Girls Just Wanna Have Fun” (1983)

    The song that started Cyndi’s meteoric rise is one of the most iconic tracks of the ’80s, and been covered many times.

  22. “True Colors” (1986)

    The title track from her sophomore album, “True Colors” was Cyndi’s second Number One hit. In the decades since its release, it’s been transformed into an anthem for the LGBT community and lent its name to Cyndi’s philanthropic organization, the True Colors Fund.

  23. “Time After Time” (1983)

    After the enormous worldwide success of “Girls Just Wanna Have Fun,” Cyndi followed up with the greatest ballad of the 80s, a majestic pop gem that still resonates over 30 years later.

Cyndi Lauper will honored at Logo Trailblazer Honors, airing June 23 at 9pm on Logo and VH1.

80's Pop Culture Expert, Shooting At The Walls Of Heartache.
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