My 53 Favorite Madonna Songs (In Honor Of Her 53rd Birthday)

We’d like to extend our fond birthday wishes to a true American icon, one Madonna Louise Ciccone, who was born 53 years ago today in the small town of Bay City, Michigan. In the space we have here, it would be impossible to adequately communicate the full extent of the impact that Madonna has had on popular culture, but suffice to say, there’s never been anyone quite like her before or since.

Just like I did for Bob Dylan on his 70th birthday, I put together the following list of my 53 favorite Madonna songs as a way for us all to celebrate the birthday of this music pioneer. These are not her “best” songs, or even her “most popular” songs, but simply, my favorites. Unlike the Song Of The Summer Countdown, this list is not pegged to any quantitative data; rather, it was generated based on conversations with my co-workers, an exhaustive deep dive into Madonna’s catalog over the past few weeks (both her songs and videos), and my own (sometimes hazy) recollection of each of these song’s influence on the culture-at-large.

We’ve got the full list for you below, but if you’re signed up for Spotify, you can also listen to the full compilation here:
My 53 Favorite Madonna Songs (On Her 53rd Birthday)

53) “Sorry” (Confessions On A Dance Floor, 2005)
52) “Everybody” (Madonna, 1983)
51) “Hanky Panky” (I’m Breathless, 1990)
50) “4 Minutes” (featuring Justin Timberlake & Timbaland)” (Hard Candy, 2008)
49) “Spotlight” (You Can Dance, 1987)

48) “Oh Father” (Like A Prayer, 1989)
47) “Amazing” ( Music, 2000)
46) “Hollywood” (American Life, 2003)
45) “Angel” (Like A Virgin, 1984)
44) “Bad Girl” (Erotica, 1992)
43) “Keep It Together” (Like A Prayer, 1989)
42) “Don’t Cry For Me Argentina” (Evita, 1996)
41) “Fever” (Erotica, 1992)

For the Top 40 Madonna songs, follow along!

40) “Die Another Day” (Die Another Day: Original Motion Picture Soundtrack, 2002)
39) “The Power of Good-Bye” (Ray Of Light, 1998)
38) “Erotica” (Erotica, 1992)
37) “Deeper and Deeper” (Erotica, 1992)
36) “Frozen” (Ray Of Light, 1998)
35) “You Must Love Me” (Evita, 1996)
34) “What It Feels Like for a Girl” (Music, 2000)
33) “Bedtime Story” (Bedtime Stories, 1994)
32) “La Isla Bonita” (True Blue, 1986)
31) “Dress You Up” (Like A Virgin, 1984)

30) “Burning Up” (Madonna, 1983)
29) “Rain” (Erotica, 1992)
28) “Who’s That Girl” (Who’s That Girl: Original Motion Picture Soundtrack, 1987)
27) “Human Nature” (Bedtime Stories, 1994)
26) “I Deserve It” (Music, 2000)
25) “This Used To Be My Playground” (A League Of Their Own: Original Motion Picture Soundtrack, 1992)
24) “I’ll Remember” (With Honors: Original Motion Picture Soundtrack, 1994)
23) “Beautiful Stranger” (Austin Powers: The Spy Who Shagged Me, 1999)
22) “Hung Up” (Confessions On A Dance Floor, 2005)
21) “Material Girl” (Like A Virgin, 1984)

20) “Don’t Tell Me” (Music, 2000)
19) “Lucky Star” (Madonna, 1983)

18) “Justify My Love” (The Immaculate Collection, 1990)
17) “Live to Tell” (At Close Range: Original Motion Picture Soundtrack, 1986)
16) “Take a Bow” (Bedtime Stories, 1994)
15) “True Blue” (True Blue, 1986)
14) “Holiday” (Madonna, 1983)
13) “Crazy For You” ( Vision Quest: Original Motion Picture Soundtrack, 1985)
12) “Secret” (Bedtime Stories, 1994)
11) “Open Your Heart” (True Blue, 1986)

10) “Cherish” (Like A Prayer, 1989)
“Romeo and Juliet/They never felt this way, I bet!” One of Madonna’s few straight up love songs, this adorably cute ditty was bested by an stunningly cinematic video directed by the legendary fashion photographer Herb Ritts. Unlike “Express Yourself” or “Like A Prayer,” the black-and-white video wasn’t high concept in nature, but it showcased Madonna’s playful side in a way that played in perfect contrast to the image of her as a lightning rod for controversy and criticism.

9) “Like a Virgin” (Like A Virgin, 1984)
Madonna’s first #1 single, with a wonderfully un-subtle video (the lion who transforms into a man!), which she then proceeded to outdo at the 1984 VMAs. “Like a Virgin” was Madonna’s grand leap into both the controversial and the iconic. Plus it inspired one of Weird Al‘s best parodies (for which Madonna herself allegedly suggested the title) and anchored the opening scene of Quentin Tarantino‘s directorial debut Reservoir Dogs, in a foulmouthed scene that made Madonna seem almost, well, virginal.—Nick Minichino

8) “Express Yourself” (Like A Prayer, 1989)
Lady Gaga was only three years old when this song first hit radio stations, which goes a long way towards explaining why “Born This Way” sounds like a carbon copy of this smash. The video, directed by a pre-Se7en and Fight Club David Fincher, combined dystopian imagery with German expressionism and became one of the most memorable videos of all-time. The song is notable for the way it all but renounces Madonna’s earlier “Material Girl” obsessions in favor of making monogamous relationships work through open and honest communication.

7) “Music” (Music, 2000)
Lots of people made winking champagne-room stripper-parody videos (even Moby, as we recall, got in on the gag). But Madonna’s wink communicates volumes more than nearly any other pop star’s, and her performance teases out the comparison without being dismissive of its appeal. The seventies typography, Ali G bits, and animated superhero/mermaid middle section make this one of the odder additions to the Madonna music video catalog (and we love it for that). As for the song, it’s an electro-pop single with the lyric “Music makes the people come together” that hit #1 even after it leaked to Napster. Only Madonna could pull that off—and deserve it.—Nick Minichino

6) “Ray of Light” (Ray Of Light, 1998)
The early 1990s were a confusing time for Madonna, as she pushed the boundaries of good taste (ie, shooting soft-core porn with Vanilla Ice!) to a point where the American public couldn’t really stomach her anymore. It wasn’t until she totally reinvented herself (once again!) in 1998 as an earthy, yoga-obsessed and quasi-New Age spiritual goddess (and mother!) that the mainstream finally embraced her again. It didn’t hurt this song’s popularity that it was on the cutting (if not bleeding) edge of music production at the time; she worked with the brilliant producer William Orbit on a sound that tweaked the trance-y rave sound pulsating through the clubs of London at the time into something palatable for Top 40 audiences.

5) “Papa Don’t Preach” (True Blue, 1986)
Madonna had already sung about being “like” a virgin in 1984, even though she made no bones about the fact that she had lost her virginity a LONG time prior to this song’s release. She has never been apologetic for her sexual persona, but in a bold and daring artistic move, she and songwriter Brian Elliot wrote a song about the heavy consequences that can come with unprotected sex. This song remains powerful to this day, and its defiant refrain of “I’m keeping my baby!” is something that I still remain surprised that Bristol Palin never co-opted.

4) “Into The Groove” (Desperately Seeking Susan: Original Motion Picture Soundtrack, 1985)
The first of her (numerous) singles explicitly about dancing, this “dorky” (her words, to Time) jam perfectly suited the gum-snapping Madonna of Desperately Seeking Susan and the proto-freestyle eighties-teen-pop dancefloor. Even with its movie tie-in, the music video still managed to prominently feature flashbulbs. This track never got the chart love it deserved, but it’s more than made up for it over the years.—Nick Minichino

3) “Like a Prayer” (Like A Prayer, 1989)
Madonna’s most controversial song and video, by a landslide. The video, which was originally sponsored by Pepsi (that is, until they actually saw it), is laced with powerful Catholic imagery (stigmata!), burning crosses, and concludes with Madonna making out with Black Jesus. And a close read of the lyrics reveals that the song is arguably about blowjobs! No one but Madonna could combine gospel choirs, strongly sexual lyrics, and an intensely personal reflection on religion and take the song all the way to #1.

2) “Vogue” (I’m Breathless, 1990)
This 1990 single—and its black-and-white music video, one of David Fincher‘s best—made manifest the connection between Hollywood style icons of the past and the dance style born in Harlem ball culture with a video choreographed by José and Luis Xtravaganza (whose own single “The Queen’s English” featured a Madonna-voiced intro). A Billboard #1 that won three VMAs (of nine nominations), the song opened ballroom culture to a massive audience without nearly the blowback Jennie Livingston got from within the community for her documentary Paris Is Burning. Twenty-one years later, no one remembers the soundtrack to the film Dick Tracy (for which the song was ostensibly recorded!) but everyone remembers “Vogue.”—Nick Minichino

1) “Borderline” (Madonna, 1983)
This, to me, is and will always be the quintessential Madonna song. She wasn’t yet saddled with the burdens of being an international icon, or figure of immense controversy, and because of that, this is song represents Madonna’s music at its purest. This incredible piece of pop music was Madonna’s first of an eventual 37 songs to place in the Billboard Top Ten, and it remains striking to this day in the way it balances playful melodies with emotionally-charged lyrics about a disintegrating relationship. It’s sort of sad, yet also sort of happy, which is a formula that many of the best pop songs of all-time utilize. This may not be Madonna’s “best” song, and it’s certainly not her most popular, but that doesn’t mean that it’s not my favorite.

Thoughts? Criticisms? Praise? You know where to leave it!

(Also, just a reminder, this list —save for “True Blue”— can be found on Spotify: My 53 Favorite Madonna Songs (On Her 53rd Birthday). Also, our friends over at Popjustice have been celebrating today, too. Check out their Madonnathon playlist on Spotify.)

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