Exclusive Features
Anniversaries, Cover Stories, Editorials,
Interviews, Lists, and Comprehensive Rankings

Madonna’s Top 20 Songs

on August 16, 2017, 1:15pm

20. “True Blue”

True Blue (1986)

It’s hard to picture Sean Penn when you listen to the cutesy love song “True Blue”, but as Madonna’s then-husband he was the lucky receiver of her heart at that time. Originally written for Penn, the retro feeling song incorporates doo wop in its chord progressions alongside Madonna’s trademark synth chords. What was more unexpected was how the song found itself being covered by the punk rock band Digger. Let’s just hope in this case they were dreaming of Madonna instead of Penn. –Allison Franks
__________________________________________________________

19. “This Used to Be My Playground”

Something to Remember (1995)

Penny Marshall not only brought us a historic film starring Madonna, but also a chart-topping single from A League of Their Own. While it’s beautiful and serene retrospective demeanor stands up on its own, it’s hard not to associate it with the film; being the film’s theme song and all. Plus, it honestly captured the heartfelt emotions of each and every one of those ball players. Just remember, there’s no crying in baseball…the dance floor, however. –Allison Franks
__________________________________________________________

18. “Open Your Heart”

True Blue (1986)

Madonna’s clever play on cabaret and female empowerment shines through in the coy pop melody “Open Your Heart”. Originally dubbed as a “simple love song”, “Open Your Heart” quickly rocketed into a feminist stomping ground for complaint no thanks to its video. Featuring a young boy seeking out a strip club, only to run away with one of its stars (Madonna) wasn’t necessarily what people wanted to see, but behind the curtain it stood for so much more. It even spawned a wacky industrial polka cover by Atom & His Package in 2001 further proving this song is more than meets the eyes. –Allison Franks
__________________________________________________________

17. “Take A Bow”

Bedtime Stories (1994)

It’s rare for a song to be both overwhelmingly sexual and heartbreaking at the same time, but “Take A Bow” hits the nail on the head. Perhaps we can blame its iconic music video for its blatant sexual nature; featuring a half-naked Madonna gyrating on her bed. Regardless, it’s not surprising that this song became her longest running single in the US, but more astonishingly her last number one single in the ’90s. I suppose “all the world is a stage and everyone has their part.” –Allison Franks
__________________________________________________________

16. “Secret”

Bedtime Stories (1994)

Madonna has received both positive and negative connotations for her sex icon status. However, in 1992, after the release of her controversial book, Sex, and her equally controversial album, Erotica, pretty much everyone was screaming in her ears, “You’ve gone too far, girl!” So, in an attempt to tone things down and show her fans/critics her softer and even sweeter side, “Secret” was released as the lead single for Bedtime Stories. However, did she achieve this? Well her coy and innocent smile in the music video speaks for itself, but the song can’t hide its true meaning for long. After all, there’s nothing sexier than a secret. –Allison Franks
__________________________________________________________

17 comments