10 Most Underappreciated Madonna Songs
Thirteen albums and 38 Top 10 Billboard Hot 100 hits later — that’s more than any artist ever, including The Beatles — there is no question Madonna has solidified her place in music as the Queen of Pop.
Songs like “Holiday,” “Vogue,” and “Like A Prayer,” are forever ingrained as tentpoles of pop culture, with every artist following in her footsteps forever trying to replicate the impact on music history that she’s had. The point is: Madonna is iconic in every sense of the word.
The only great tragedy of her career? For every “Lucky Star” and “Express Yourself,” there are just as many unsung masterpieces from deep within her catalogue and lesser hits that haven’t stood the same test of time in the general public’s consciousness.
A majority of the songs featured here are tracks that highlight how mature and powerful Madge’s voice has become over the years, and cuts that truly showcase just how great of an artist she really is. She’s come a long way from her squeaky “Material Girl” days, and it’s something she doesn’t get enough credit for. She might be thirteen albums and over 30 years deep into her career, but she is a prolific icon of music that no one will ever be able to replicate, and isn’t giving up her title as Queen of Pop anytime soon — nor should she.
We begin our list with the closer of Madonna’s eighth studio album, Music. This sparse, acoustic driven track, produced by William Orbit, was the only song written solely by Madonna from the album. The track see’s Madge grappling with her longevity as an artist and icon, and lets us know she’d leave the spotlight long before she’d let anyone try to get rid of her. “Selling out / Is not my thing / Walk away / I won’t be broken again / I won’t / I won’t fall apart,” she soothingly sings. It is certainly one of her best album closers.
Bedtime Stories in general is one of Madonna’s more overlooked efforts, especially its lead single. After lukewarm reception to her previous record (Erotica), Madonna decided to go with a more toned down approach, resulting in Bedtime Stories — an album that still lyrically touched on the subjects of romance and sex, but in a less aggressive approach than Erotica. Written and produced alongside Dallas Austin, “Secret” see’s Madonna trading in the big dance tracks she was known for at the time in favor of experimenting with R&B styles.
Hard Candy wasn’t her strongest effort as a whole, but did have a few bright moments, and “Miles Away” was one of them. This hypnotic ballad to long-distance relationships was written and produced alongside Justin Timberlake, Timbaland and Danja. It’s one of her finest vocal performances on Hard Candy, and broke the record for the most number-ones from an artist on Billboards Dance Airplay chart, being her seventh consecutive one. Always breaking those records!
In true Madonna fashion, Confessions On A Dance Floor was a complete 180 from the previous American Life. Confessions was a full-on modern disco epic that proved she could still make a crowd dance just as much as she could in the ’80s. “How High” is one of Confessions‘ most introspective moments that sees Madonna questioning if the fame and fortune are really worth it after all. “How high are the stakes / How much fortune can you make / Does this get any better / Should I carry on / Will it matter when I’m gone,” she sings. Only she could turn such deep, questioning lyrics into a club-ready dance track.
“Keep It Together”
“Brothers and sisters / They’ve always been there for me / We have a connection / Home is where the heart should be,” Madonna sings on this lost hit. Although released as Like a Prayer’s sixth and final single and reaching number 8 on the Billboard Hot 100, this ode to family is often overshadowed by the major success of “Like a Prayer” and “Express Yourself,” and has since slipped into anonymity within her catalogue. But it stands as one of Like A Prayer’s strongest lyrical moments.
Madonna’s more recent releases have proved to be less experimental than some of her earlier work, but this cut from her newest album, Rebel Heart, is one of the album’s most lyrically satisfying moments. The piano driven ballad see’s Madonna dealing with the aftermath of being taken advantage of in a relationship, singing, “You got just what you came for / A bit of fame and fortune / I’m no longer needed.” It is one of Rebel Heart’s more earnest moments.
“I’d Rather Be Your Lover”
Another one of Bedtime Stories‘ overlooked moments, it’s a shame “I’d Rather Be Your Lover” was never released as a single or received an accompanying music video. Continuing in the same R&B direction as “Secret,” “I’d Rather Be Your Lover” see’s Madonna calling bulls–t on the friend zone. “I could be your sister, I could be your mother / We could be friends, I’d even be your brother / But I’d rather be your lover,” she croons. The original version was set to include Tupac Shakur, but didn’t make it onto the album, although it can be found online. There’s no question it would be much more popular had the released version included Shakur.
“I Deserve It”
Another primarily acoustic cut from Music, “I Deserve It” is one Madonna described as a “lonely” love song. Producer Mirwais Ahmadzai specifically left Madonna’s vocals untouched on the track; something she was initially hesitant about because she hadn’t done it in such a long time, but the decision resulted in the one of the album’s strongest vocal moments.
“Deeper and Deeper”
By far Erotica’s strongest moment, “Deeper and Deeper” might just be one of the greatest disco-infused dance epics of the early ’90s — but one that still holds up today. The song see’s Madonna ditching parental advice and allowing herself to fall headfirst in love. “I can’t help falling in love / I fall deeper and deeper the further I go,” she sings. The song also includes a flamenco bridge breakdown and lyric samples from her own “Vogue” at the end. It is one of Madonna’s greatest tracks, and one that doesn’t nearly get the credit it deserves.
While American Life was polarizing among critics and fans alike upon its release in 2003 due to its heavy political nature, it has since found a place in Madonna’s catalogue as one of her most prolific releases. This folk rock-infused gem has long been considered a highlight of American Life from critics and fans alike, and a prime example of how the early 2000s saw Madonna releasing her best vocal work. The song sees Madonna dealing with life’s many uncertainties, singing, “There are too many questions / There is not one solution / There is no resurrection / There is so much confusion.” It’s a moment that demonstrates how introspective Madonna is sometimes the best Madonna of all.