From controversial choices to popular picks, this is a look inside my lifelong Madonna fandom.
August 16, 2018 marks the 60th birthday of Madonna, an artist who changed my life and shaped my upbringing as a gay man. The difference she's made in the LGBTQIA+ community cannot be quantified. From spreading awareness and reducing stigma around HIV/AIDS, to creating the Raising Malawi organization to benefit the African country of Malawi, her impact goes far beyond pop music.
Still, the Queen of Pop has an vast and vivacious catalog of hits and album tracks, and these are my sixty favorites. From songs that defined her legacy, to forgotten gems, I hope you'll enjoy this celebration of her music.
60. "Gang Bang"
Less a song than a visceral ride through Madonna’s psyche after her divorce from Guy Ritchie. It's so explicit that it couldn't even be edited to appear on the "clean" edition of the MDNA album.
59. "Over and Over"
Easily written off as a frothy filler track, the song’s lyrics explore Madonna’s can-do spirit, which cannot be broken.
58. "Hey You"
An inspiring climate change anthem released for Live Earth. Simple and uplifting, this sweet-hearted song was wrongfully panned by critics.
57. "American Life"
“Madonna attempts rapping” was the headline from this banger, but the real headline should have been her brilliant, scathing take on fame and George W. Bush’s post-9/11 America. Its banned and retracted original music video is one of Madonna's most profound artistic statements ever.
56. "Burning Up"
The quintessential "young Madonna" song. It's entirely fueled by the personality that made her the biggest star in the world, and led to her being dubbed "the female Michael Jackson" from the start of her career.
55. "Where’s The Party"
Just a fun song. You can't help but groove along.
54. "Don’t Stop"
This is such a low-key song... but when you're in its grasp, it's inescapable. I had this on repeat a couple summers ago.
53. "Spanish Lesson"
This pick will make a lot of serious Madonna fans roll their eyes - but to me, this is one of her most fun '00s tracks. A flirty, bubblegum pop moment with clever verse lyrics and a big chorus.
52. "Take A Bow"
Madonna produced this with legendary R&B singer-songwriter Babyface, who later went on to collaborate with Barbra Streisand on her 2014 Partners album. Fittingly, Apple Music compares "Take A Bow" to a big Streisand ballad.
51. "Deeper and Deeper"
One of the most unexpected and exciting moments of experiencing the Rebel Heart Tour live was hearing Madonna take on this '90s jam in a style faithful to the studio version.
50. "Gambler"
Never released on a studio album or greatest hits collection, this forgotten Madonna hit remains beloved by woke fans.
49. "Secret"
48. "Die Another Day"
In my world, this is the best James Bond movie song of all time.
47. "I’m Addicted"
The sputtering, trippy song that inspired the title of Madonna's MDNA album. The production on this one is insane. I'd love to have been a fly on the wall while Madonna and co. produced this. Or any song, really.
46. "Lucky Star"
The premiere bubblegum pop song, "Lucky Star" remains fresh and fun.
45. "Give It 2 Me"
While it was absolutely the wrong choice to follow-up "4 Minutes" as the second single from Hard Candy, "Give It 2 Me" stuns with its Pharrell-assisted beat and occasionally silly lyrics. Madonna fans were quick to call out P for reusing the drums in the 2013 song of the summer "Blurred Lines (feat. T.I. & Pharrell)" by Robin Thicke.
44. "Amazing"
One of the best deep cuts that makes Music the wonderful album it is.
43. "Some Girls"
Another glittering moment from the misunderstood MDNA, this William Orbit collaboration is the sonic equivalent to a sputtering laser light show. Lyrically, Madonna presents a sassier take on her Millennial pop star competition with this one.
42. "4 Minutes (feat. Justin Timberlake & Timbaland)"
A giant dance song with over 100 audio tracks used in its composition, “4 Minutes (feat. Justin Timberlake & Timbaland)” reminds me of listening to Hard Candy in a car full of high school friends.
41. "Fighting Spirit"
A Confessions On A Dance Floor box set bonus track that feels like it should have made the standard edition of the album. It's just that good. Listen if you haven't.
40. "Justify My Love"
39. "It’s So Cool"
This sarcastic bop is a look at Madonna’s cynical side, and a deluxe bonus track from her 2009 greatest hits album Celebration.
38. "Nobody Knows Me"
The Re-Invention Tour performance of this is so brilliant:
37. "Celebration"
36. "Future Lovers"
One of the first songs that helped me accept myself as a gay man.
35. "Unapologetic Bitch"
Another hit that got away.
34. "Papa Don’t Preach"
I remember first hearing this as a kid, and finding the subject matter scandalous.
33. "Live To Tell"
32. "Spanish Eyes"
I remember listening to the full Like A Prayer album for the first time on vinyl, and falling in love with this song.
31. "Human Nature"
As a huge Britney Spears fan, my first experience with this song was watching the Sticky & Sweet Tour performance of it where Britney appears in the video backdrops.
30. Bitch I’m Madonna (feat. Nicki Minaj)
A crazy sendoff to ageist haters, this mammoth dance track also features one of Nicki Minaj's best rap verses ever. My favorite memory of this song is watching Madonna's insane performance of it on The Tonight Show.
29. "Revolver (feat. Lil Wayne)"
If marketed properly, this could have been a major US hit. Lil Wayne was at the top of his game at the time, and this song is a slice of pop perfection.
28. "Voices"
Part of what makes Hard Candy such an underrated album.
27. "Joan of Arc"
Madonna at her most vulnerable.
26. "I Love New York"
This first appeared as a rock & roll bonus track on the I'm Going to Tell You A Secret CD, before being rerecorded as a dance song for the Confessions On A Dancefloor album.
25. "Girl Gone Wild"
24. "Love Song"
A lot of people don't know that Madonna collaborated with Prince on her 1989 album Like A Prayer. This is because his guitar work on "Like A Prayer," "Keep It Together" and "Act of Contrition," and vocals on "Love Song" are uncredited. Michigan native Madonna spoke about the chilly Minnesota winter experience recording "Love Song" at Paisley Park:
“We were friends and talked about working together, so I went to Minneapolis to write some stuff with him, but the only thing I really dug was ‘Love Song.’ We ended up writing it long-distance, because I had to be in LA and he couldn’t leave Minneapolis, and quite frankly I couldn’t stand Minneapolis. When I went there, it was like 20 degrees below zero, and it was really desolate. I was miserable and I couldn’t write or work under those circumstances.”
23. "Candy Shop"
Maybe it’s the bubbly drums, maybe it’s the fact she’s performed this non-single on her last three world tours. Who knows? It’s a major grower. Thanks, Pharrell!
22. "Rebel Heart"
A confessional, upbeat song that maps the journey Madonna had to take to become the Queen of Pop she is today. Inspired me to get my first tattoo, which was the Rebel Heart album logo. The demo version of this song has a catchy vocal hook in the background that repeats throughout.
21. "Me Against the Music" - Britney Spears (feat. Madonna)
Madonna does the unthinkable: guest stars on a song. This track was complete when Britney played it for her, Madonna offered to make it a duet. The result is a wild meeting of the minds of two of pop music’s all-time greatest stars. I remember watching the MTV “Making the Video” special on MTV, and freaking out when I realized the VCR didn't record it properly.
20. "Material Girl"
This was the first '80s Madonna song I fell in love with.
19. "Love Profusion"
Featuring profound lyrics and experimental production, this song captures what it must feel like to be in the honeymoon phase of a relationship with Madonna.
18. "Open Your Heart"
Catchy, catchy, catchy.
17. "Express Yourself"
"Look it up" - Madonna
16. "Like A Virgin"
I can't help but think of this iconic moment:
Photo: Billboard
15. "Isaac"
This song has a raw power which cannot be denied.
14. "Sorry"
A dance floor stomper that beautifully picks up where "Hung Up" left off; it's no wonder its music video does the same.
13. "Love Spent"
On an album filled with references to her divorce from Guy Ritchie, this multi-faceted song stands out as her definitive statement on the subject. The abrupt transition midway through makes way for an almost entirely new song, and feels like an epiphany.
12. "Holy Water"
A percolating pop banger that feels dangerous and lyrically provides an updated, distilled version of her career-long focus on Catholicism. The Rebel Heart Tour performance of this is worth the cost of the Blu-ray set alone.
11. "Beautiful Stranger"
Described by Apple Music as “one of her brighter, deeper singles ever,” and I couldn’t agree more. This was the first Madonna song I was obsessed with in real time when it came out.
10. "The Power of Good-Bye"
It took me a while to mature to the point where I could fully appreciate this song. It's a gorgeous, supremely well-written song.
9. "Ray of Light"
Over 5 minutes of pure, enlightened pop bliss.
8. "Like A Prayer"
Controversial and powerful, this iconic pop power ballad reigns supreme as #1 on the majority of mainstream writers’ top Madonna songs lists, and I can see why.
7. "Oh Father"
Madonna has explored her mother’s death throughout the years, but no other work is more candid or haunting than this largely overlooked ballad. Sia has a wonderful cover of this, too.
6. "Hung Up"
You’d think the prominent ABBA sample would define the song, but Madonna’s superpowers ensure the track would be solid without it.
5. "Devil Wouldn’t Recognize You"
The type of maturity and depth critics claim they want to hear in modern Madonna music, but seemingly ignore.
4. "Don’t Tell Me"
Uses country music elements to speak to her biggest detractors, middle America, in a send off that is both powerful and universal.
3. "Frozen"
A still from the haunting music video.
No other cut on “Ray of Light” showed more artistic growth than “Frozen,” an extremely atmospheric song that analyzes depression.
2. "Vogue"
Madonna with beloved backup singer Niki Harris.
A historic track that sounds fresh today, “Vogue” effortlessly changed the world by starting conversations and offering the general public a glimpse into queer culture.
1. "Music"
The Queen of Pop defines music itself in the ultimate ode to the dance floor experience. I had full-body chills during her Super Bowl performance of this.
What's your favorite Madonna song? Tweet me! @DerekPlease on Twitter.