Like a Virgin: My Journey through Madonna's Discography

Why I'm Listening to Every Single Madonna Album For the First Time

As someone who still uses iTunes and collects MP3s, I've become somewhat obsessed with collecting cherished but forgotten songs from my childhood. I listen and scour through playlists of "the best [genre] songs of [decade]" in search for songs or artists that I enjoyed while growing up but have since forgotten about. Sometimes I'm delighted to find that multiple songs I fondly remember are by the same artist. Usually it's no more than a handful.

Madonna in 1983 during her first tour

So when I realized that Madonna was responsible for multiple songs I cherished from not one, not two, but three decades of music, I took notice. It seemed to me that while many artist's careers span several decades, very few are able to stay relevant to the pop radio stations for as long. This discovery warranted more of my attention. Not only did I want to comb through her hits to find more hidden gems from my childhood, but I felt compelled to listen through all of Madonna's music out of sheer curiosity for how an artist could make such an impact for such an extended period of time.

So began my self-imposed quest to listen through every single Madonna studio album and single in chronological order for the first time in my life. To track my thoughts, I'm going to document here what I thought of each of her albums and pick a single favorite track from each. I'll then recap the experience and my thoughts on Madonna's career as a whole, ending with a declaration of my favorite album and, if possible, favorite track.

But first, for context: I knew very little about Madonna or her music before embarking on this quest. Mostly, I was aware that she was a popular artist and that she made a song that Weird Al parodied and Tarantino was obsessed with dissecting. I had heard plenty of her hits before, but I didn't consciously know that she was the artist responsible for creating all of them.

DISCLAIMER: I am by no measure a music expert, and my thoughts will reflect as such. I just like listening to music, so my apologies if I overlook some brilliant technique or meaning that better-trained and educated ears would pick out.

Madonna (1983)

I'm a fan of 80s pop music, so I was quite excited to listen through this album and I was not disappointed. Madonna's self-titled debut is quite a fun listen, and I had extra fun in comparing it to the debut albums of my favorite female pop stars from today. The album starts off strong with the incredibly danceable "Lucky Star" and this energy is wonderfully sustained throughout the whole album. Even when "I Know It" feels like it falls just short of missing the mark and might indicate the album's second half trending downward, "Holiday" quickly erases all doubt that the second half will be anything less than stellar.

Overall, I love how 80s this album is. The synths and guitars just make me happy.

Favorite Track: "Lucky Star"
While I think "Holiday" is an objectively better and stronger song (and it's very tempting to claim it as my favorite of the album), there's just something incredibly charming about "Lucky Star" that I can't put my finger on. Maybe I'm just a sucker for how 80s it sounds.

Like a Virgin (1984)

Coming out only a year later, this album feels like a natural extension of the previous, albeit there's an added confidence to the music and vocal performance. "Material Girl" is a banger of an opening track, but "Like a Virgin" is the obvious standout here for not only the quality of the music but also the lyrical content. Where "Physical Attraction" on her debut album felt like Madonna somewhat hesitantly dipping her toe into the water of playful sexual content, "Like a Virgin" is her confidently diving all the way in. You can hear just how much fun she's having in recording the vocals, and the music wonderfully matches her energy. This song is especially fun to listen to after learning that it (and her performance of it on the 1984 VMAs) was controversial at the time, because not only is it tame by today's standards but it's evidence of her influence on future female pop stars and music as a whole.

That said, the album doesn't grip me as much as the self-titled debut did, despite the quality being undeniably superior. There's just something special about that debut album that I can't put my finger on. However, the inclusion of "Into the Groove" on the 1985 re-issue definitely helps to boost the album's overall quality.

Favorite Track: "Like a Virgin"

This was another tough choice, with "Material Girl" being a solid contender. But in the end, the enthusiastic vocal performance and thumping beat of "Like a Virgin" won me over.

Movie Singles: "Crazy For You" & "Gambler" (1985)

So the movie these are from (Vision Quest) looks pretty mediocre, but oh man the song "Crazy For You" is anything but. Such a beautiful, emotional romance song. I'd be surprised if this wasn't a popular song at weddings, though I wasn't fortunate enough for it to be played at mine. On the other hand, "Gambler" is a playful dance song that would feel right at home on Madonna's self-titled album, but as a single it just doesn't stand out as much as others in her discography.

Favorite Track: "Crazy For You"
Obviously.

True Blue (1986)

This album feels like a real step forward. It's like Madonna has combined the heart and soul of her debut album with the skill and confidence of her second. As has become the norm, the album starts off very strong with the dance singles "Papa Don't Preach" and "Open Your Heart" before diving into the more diverse pop music sound.

As a bonus, I had to double take for the song "Live to Tell" because it turns out its intro was the source of a slowed-down sample in the opening song of one of my favorite vaporwave albums, and while it was odd to get used to the normal-speed version at first, it was a pleasant surprise to finally hear the sample in its original context.

Overall, unlike her previous two albums, no song really feels like a lull here.

Favorite Track: "Open Your Heart"
While this album is full of great tracks, "Open Your Heart" was the obvious pick for me. Not only was it a childhood favorite so it's got nostalgia points, but it sounds like the type of track you could set a badass montage to—it gets me pumped up!

Movie Singles: Who's That Girl soundtrack (1987)

Wow this movie looks bad. James Foley has had an interesting directing career, from the excellent Glengarry Glen Ross and some solid work on critically-praised modern television shows to the nearly unwatchable Fifty Shades sequels. Anyway, that's irrelevant because I only need to listen to the Madonna songs from the soundtrack.

"Who's That Girl" is a decent enough theme song, but it doesn't really stand up on its own. "Causing a Commotion" fares a bit better as a single. "The Look of Love" is a solid song with a nicely executed ethereal quality. "Can't Stop" is a passable dance pop song.

Favorite Track: "Causing a Commotion"

None of these songs did much for me, but "Causing a Commotion" came the closest.

Like a Prayer (1989)

Coming up on the last Madonna album of the 80s, Like a Prayer starts out strong with the title track followed by "Express Yourself," followed by an assortment of some more experimental tracks. While I'm not really a fan of tracks like "Promise to Try," "Dear Jessie," "Oh Father," or "Spanish Eyes" (so many ballads!) that stand out as experimental for Madonna's style, they're certainly well made and hold artistic value that I'm sure others enjoy very much. For my part, however, "Cherish" comes off as classic Madonna in the best way, while "Keep It Together" comes close to scratching the same itch while also containing qualities that sound distinctly of the 90s pop variety.

Overall, I'm not a huge fan of this album, as it's a bit too ballad-heavy for me and both "Keep It Together" and "Act of Contrition" smell a bit too thick of the 90s pop that I'm not very fond of. Still, the three tracks I do enjoy are very strong additions to Madonna's catalog. I just worry where the 90s will take her music.

As a side note: I had just listened to Tove Lo's album Lady Wood the day before listening to Like a Prayer, and it was interesting to see the similarities in the album art of each, though by Tove Lo's own admission the homage was completely unintentional.

Favorite Track: "Like a Prayer"
Easy pick. This one has gotten stuck in my head several times since I listened to it. The mixture of choir-like verses with a catchy pop chorus is brilliant.

I'm Breathless: Music from and Inspired by the Film Dick Tracy (1990)

I almost overlooked this album completely since it's technically considered a soundtrack album, and actually only discovered it after first moving onward and listening to Madonna's first proper studio album of the 90s: Erotica. That said, I'm very, very glad I went back and found this album. The jazz and swing influences work really well here (or at least really appeal to me) and go a long way toward showing just how versatile Madonna is.

"He's a Man," and "Hanky Panky" are particularly strong tracks in the beginning of the album. "I'm Going Bananas" comes out of nowhere as a salsa song where Madonna puts on a Spanish accent, which may or may not be considered offensive today but it works. "Back in Business" does a great job alternating seamlessly from mysterious dreamlike jazz to upbeat swing. Especially noteworthy is the transition from the classic swing style of "Now I'm Following You (Pt. 1)" to the modern pop aesthetics of "Now I'm Following You (Pt. 2)," which breathes new life into the end of the album — concluding with the amazing classic single "Vogue."

Favorite Track: "Vogue"
I was really tempted to pick one of the jazz or swing songs for their uniqueness, or "Now I'm Following You (Pt. 2)" for basically inventing the electro swing genre, but alas, "Vogue" is just too good. I'd bet almost nobody can think of a fashion runway without thinking of this song.

Erotica (1992)

Wow, talk about a genre shift. This album is pretty much all in the style of trance, though the track "Where Life Begins" gives me trip-hop vibes. Not only is this reassuring that Madonna's music may not have succumbed to the trends of 90s era pop, but as someone nostalgic for 90s trance and trip-hop this album comes off as a pleasant surprise. "Erotica," "Deeper and Deeper," "Where Life Begins," "Bad Girl," "Rain," and "Did You Do It?" are personal favorites.

What's also great about this album is its apparent impact on modern pop music. While there were eight years and several albums between this and her controversial appearance on the VMAs performing "Like a Virgin," this album marks Madonna firmly re-establishing herself as pushing the boundaries about what's appropriate to talk and sing about, with specific emphasis on sexuality and femininity. Some quick research shows that this era in Madonna's career was in fact rife with controversy thanks to this album, a coffee table book with explicit photos of Madonna, and an erotic thriller film starring the singer. Being that this was only 1992, I think it's safe to say she set the stage for the likes of Lady Gaga and Miley Cyrus to push boundaries and stir up controversy.

Favorite Track: "Rain"
This track just stands out from the rest. It's beautiful.

Movie Single: "I'll Remember" (1994)

This song is just fantastic, and it was one of my childhood favorites. Words cannot describe how happy I was to rediscover this song and find that it is every bit as beautiful as I remember it being. I love it.

Favorite Track: "I'll Remember"
Well this was an easy pick.

Bedtime Stories (1994)

In yet another genre shift, this album features many R&B inspired tracks. This is also the first Madonna album where the first few songs didn't completely grab me. That isn't to say that these songs are bad, of course, but they just didn't excite me for the album as much as is typical of the first three tracks of any Madonna album up to this point. In fact, this album as a whole is lacking in the energy that I've come to expect and love about Madonna's work, though I suspect that's perhaps due to the R&B influences resulting in a more relaxing sound.

In any case, I'm relieved that this album still manages to steer away from the trends of pop music in the 90s, and there are definitely tracks that stand out to me. Specifically, "Don't Stop," "Forbidden Love," and "Bedtime Story," the latter of which sounds like it could fit at home on a Massive Attack album, which I totally dig.

Favorite Track: "Bedtime Story"
This song reminds me so much of classic Massive Attack that I couldn't even consider anything else on the album being even close to my favorite.

Singles: "You'll See" and "One More Chance" (1995)

Taken from the compilation Something To Remember, "You'll See" is the standout track for me of these two, especially thanks to the growing intensity of the track and the accompanying Spanish-style guitar. "One More Chance" is solid (especially the latter half), but not nearly as strong by comparison.

Favorite Track: "You'll See"

As I said, this one's got a great buildup.

Please note that I'm skipping the Evita singles, since those songs were merely sung/covered by Madonna but were written for a stage play.

Ray of Light (1998)

I think "Drowned World/Substitute for Love" is one of the best opening tracks to any Madonna album so far. Not only was the new style totally unexpected (I should just start expecting the unexpected at this point) but it single-handedly rebuilt my hype for listening through all of Madonna's albums. Once again, Madonna is experimenting with genres here and this time I can confidently say she is totally nailing it.

To further emphasize how hard this album hit me, I should mention that up until this point I was still considering Madonna's first album to be my favorite. After all, I'm a sucker for 80s dance pop. But then, a mere two songs into this album, I began to question if that were still the case.

Continuing through the album, "Ray of Light" had me bobbing my head and tapping my feet at my work desk like nothing that had come before. "Candy Perfume Girl" had me grooving to the beat. "Sky Fits Heaven" pleasantly reminded me of some early BT music. "Frozen" stood out in a way I have no clever words for. Oh, and as a relatively new father I really connected with "Little Star."

Favorite Track: "Candy Perfume Girl"

This was a tough picks given the album has so many fun tracks, but my gut says this song is going to stick with me the longest.

Movie Single: Beautiful Stranger (1999)

Closing out the 90s is this track from the first Austin Powers movie, and while it's not particularly noteworthy, it is a solid track to end Madonna's second decade on.

Favorite Track: "Beautiful Stranger"

Another easy pick!

Music (2000)

What the hell? Just when you think she's done making mainstream hits she comes out with songs like "Music" and "Don't Tell Me," the latter of which was a favorite of mine in the early 00s. It kind of feels like this is the first album since the 1980s where Madonna is making mainstream dance pop rather than experimenting with lesser known genres. Fortunately for me, I'm a sucker for dance pop. The album also does a good job of playing within the genre to find different sounds, but that's pretty typical of Madonna. Overall I'd say this is up there with her best albums so far. "What It Feels Like for a Girl" is a track that especially stood out for me, though there's really nothing on this album that I didn't really enjoy.

Perhaps my biggest takeaway with this album is that you can't judge an album by its cover, or maybe it's that the marketing team should have chosen a cover image that better represented the album's sound? I was worried going in that this would be a country pop album (I'm not a country fan) based on the very obviously country-inspired album cover, but fortunately that wasn't the case at all. I'm convinced that there must be a reason for the country visual aesthetic, but I'm not smart enough to figure out what it might be.

Favorite Track: "Don't Tell Me"
"What It Feels Like for a Girl" is a close second here, but "Don't Tell Me" is just too catchy to deny. That being said, I could see the former track overtaking the latter as my favorite on repeated listens, but that's just speculation.

American Life (2003)

This is the first time that the first track on a Madonna album came off as uneven to me. While "American Life" sounds like a technically well-made song, it also sounded deliberately inaccessible. The album has a rebellious and somewhat somber quality to it, which is highlighted by the album cover's black, white, and red graffiti-style artwork. This change in attitude seemingly comes out of nowhere from an artist who seemed pretty high on life up until this point — until you realize that this is Madonna's first post-9/11 album, and then it all makes sense. That event and the ensuing war had a huge impact on American culture. I saw a similar shift in 2007 with Nine Inch Nails' politically-charged album Year Zero, and of course everyone knows how hugely popular Green Day's rebellious album American Idiot was in 2004.

As for the music itself, there's nothing quite as instantly lovable as the singles on previous albums, but there's still some really good stuff here. "I'm so Stupid." "Love Profusion," and "Nothing Fails" stand out in particular. "Die Another Day" is a decent track for the album but a totally weird addition to the 007 theme song catalog that I always assumed was by Britney Spears. Overall it's a solid if somewhat uneven album.

Favorite Track: "Love Profusion"

Nothing really stood out to me as an obvious pick on this album, but this song came closest.

Confessions on a Dance Floor (2005)

Ah, here we are back in familiar territory. "Hung Up" starts this album off on the right foot, "Future Lovers" stood out as a fun track that I was surprised wasn't a single, and "Jump" is in a great position on the album to help carry the energy through to the end. While it's great to hear Madonna returning to upbeat dance pop here, it's admittedly a bit disappointing that she's experimenting less than I'm used to here, though I'm sure there's plenty more of that to come as well. Overall, this is a solid dance album, though there's not a lot of catchy pop to sink my teeth into, if that makes any sense.

Favorite Track: "Hung Up"

Easy pick. Nothing else on the album really comes close.

Charity Single: Hey You (2007)

Charity songs tend to be weighed down by their obvious preachy message that doesn't allow for much creativity, lyrically, and are typically ballads, regardless of the musical style of the musician(s) involved. That said, this one's at least not totally unoriginal, lyrically, and the ballad style comes off pretty sincere instead of forced and obligatory. I'd take this any day over that appalling "Earth" charity track from Lil Dicky.

Favorite Track: "Hey You"
Is this joke of picking a favorite track from a single song getting old yet? Probably.

Hard Candy (2008)

Ah yes, here's the hip-hop influence of the 00's creeping in. Despite the fact that I don't recall ever hearing "Candy Shop" before, it sounded very familiar to me, likely because I started dating my hip-hop-loving wife around this time so this style makes me nostalgic for those early days of our budding relationship. Speaking of, "4 Minutes" is an absolute banger that really takes me back, since I definitely heard this one several times before thanks to my wife, who was not only into hip-hop but was and remains a huge fan of Justin Timberlake. After these two tracks, the album continues to deliver plenty of fun tunes. "Beat Goes On" was an especially stand-out track for me, thanks in part to the surprise appearance of a wild Kanye West. Overall, this is a very catchy album that I think holds up very well, especially as a snapshot of what style of music was popular at that time.

Favorite Track: "4 Minutes"
Sometimes I wish I  could be more surprising and pick a song other than one of the hit singles, but then I hear songs like this and remember why those were hit singles.

Singles: "Celebration" and "Revolver," (2009)

Closing out the third decade of her career is the compilation album Celebration, featuring two new songs. Unfortunately, neither of them really does much to stand out.

Favorite Track: "Revolver"
"Celebration" just sounds way too forgettable, so "Revolver" wins by default.

A Pause to Reflect on the Pop Industry

I think it's important to note here as we move into the 2010s that it was during this time that Katy Perry and Lady Gaga both exploded onto the pop music scene. I'm no expert in musical trends, but I know that Katy Perry and Lady Gaga were huge in moving the genre forward into the next decade. In fact, both put out their successful debut albums in the same year as Madonna's Hard Candy (One of the Boys and The Fame, respectively), but by the time Madonna released her follow up MDNA, Lady Gaga also released The Fame Monster EP and Born This Way, solidifying her position as a huge presence in the industry (and someone who I now realize clearly drew influence from Madonna), and likewise Katy Perry had also released Teenage Dream, which I'm convinced is one of the best pop albums of the last 20 years. These, along with many other talented artists, emerged as new and exciting voices in the industry (Taylor Swift also notably shifted to pop music in 2012). Although Madonna had impressively managed to stay relevant for three decades, it seems to me that her work going forward would be cut out for her.

MDNA (2012)

Here's where my expectations have once again fooled me. By this point in her career I was expecting the unexpected, which is to say I expected MDNA to be more experimental, but it comes off as yet another mainstream dance pop album similar to Hard Candy, Confessions on a Dance Floor, and Music. Sure, the style itself continues to evolve with the use of harder beats and occasional dubstep production and the like, but it feels like Madonna's magic and charm has been sacrificed in exchange for generic danceable beats. While there was a stretch of albums where I felt consistently surprised and impressed by Madonna's skills and willingness to try new things, this album feels like a low point in her career.

As a point of comparison, while the album Bedtime Stories didn't do much for me, personally, I could still appreciate the quality and effort put into it. MDNA, however, doesn't feel like there's much to truly appreciate in it. There's nothing new and surprising happening. "Gang Bang," "I'm a Sinner," and "Some Girls" might be the only songs I enjoyed on this album. While "Give Me All your Luvin'" has a catchy beat, it comes off as somewhat flat and the addition of Nicki Minaj's vocals doesn't do it any favors. Overall, I got the sense while listening to the album that the tracks were incomplete demos rather than the fully-polished songs I'd come to expect.

Favorite Track: "Gang Bang"

I guess?

Rebel Heart (2015)

My first thoughts when hearing the first song "Living For Love" on this album were "thank goodness she's back with something good." Likewise, "Devil Pray" eased any concerns I had that the opening track would be a one-off in terms of quality, and proved to be an exceptionally good track in its own right (the late great Avicci's influence in this track is obvious). Heck, even Nicki Minaj is utilized well in "Bitch I'm Madonna" such that I wasn't repulsed by her inclusion in the song. The "HeartBreakCity" ballad even sounds like it somehow fits perfectly in the overall sound of the album, despite my prior dislike of Madonna's ballads — and furthermore "Body Shop" (which is almost like a ballad as well) took a surprisingly good turn at about the halfway point.

Other songs I just need to mention because they surprised me with how great they were: "Ghosttown," "Illuminati," and "Holy Water."

Is this Madonna's best album since Music? I think it might be.

Favorite Track: "Body Shop"
This song just grabbed my attention and didn't let go. The first half is already beautiful musically and vocally, and the change in the second half takes it to another level.

Madame X (2019)

Here we are at the end of our journey and the end of yet another decade of Madonna music. After four albums straight (and almost two whole decades) of pretty mainstream dance pop, this album features a welcome return to Madonna's penchant for experimentation that made up the majority of her 90s albums. "Medellin" sets the stage perfectly with Spanish guest vocals by Maluma and a beat to match. "Dark Ballet" continues to surprise with heavy use of a Nutcracker sample and vocoder, and "God Control" mixes it up again with a funk-inspired beat and a groovy 6 minute run time.

Unfortunately, although there's a lot of creativity and talent on display in this album, it's devoid of the type of catchy dance pop songs that draw me in. None of the songs really stood out as must-listen to me on this album. It's hard to describe the disappointment and guilt I feel when I hear music that's obviously very well-made, but just doesn't do anything for me. That disappointment and guilt is greatly multiplied by the fact that this is the last Madonna album in my journey.

Favorite Track: "God Control"
I may not love any songs on this album, but I liked this one the most.

Reflecting on Madonna's Whole Discography

There you have it. I just listened to all of Madonna's discography in chronological order for the first time in my life. I honestly wasn't expecting to enjoy her music as much as I did in the first two decades, and although there's a certain magic missing in the later two decades of her career, I also wasn't expecting to find so many of the memorable songs in that latter half as I did.

Pop is an interesting genre for me. I've never had a favorite pop artist in the way that I have favorite artists of almost every other genre because while I can fall completely in love with a good pop song, there's something about the commercial or superficial quality of it that always fails to make me connect with it on any deeper level. I just don't connect the creators as much as I do with those of other genres. I started to think that was going to change as I listened through Madonna's first handful of albums, but then I got to the 90s albums and the sound that had defined Madonna's personality for me—the thing that I connected with—disappeared completely and was replaced with decade-appropriate genre experimentation. My connection to Madonna faded even more with the onset of the 2000s albums, because while I very much enjoy many of those dance pop songs, they're such a far departure from the sound that I fell in love with that it's hard to make peace with the fact that they're from the same artist.

Madonna in 2019 during her most recent tour

Therein lies the challenge with being a pop star. The trends in the sound of pop music are constantly changing. New, younger artists are innovating all the time. I don't know if Madonna's style changed with the times because she was trying to remain relevant, if she was genuinely moved by the changes in the genre and wished to try her hand at them, or if she just always made exactly what she wanted to despite what was popular at the time, but as a first-time listener it's jarring to hear the changes. While an artist like Nine Inch Nails is constantly experimenting and changing over the course of three decades, it's always within the confines of some larger idea of what that band is meant to sound like so that even something totally new and unique sounds unquestionably like it belongs with something released two decades earlier. I don't know that I could listen to "Lucky Star" next to "God Control" and get the same sensation.

That said, this was quite an enjoyable journey. I've never listened to any artist with so many albums through from beginning to end like that, and the fact that Madonna's style changed so much only made it that much more interesting. I am now a lifelong fan of some of the songs I discovered, and although I can't say I'm a lifelong fan of Madonna as well, I will certainly continue to watch her career and listen to each release with much interest. And so, without further ado:

Favorite Album: Uhhh.....

I really thought I was going to be able to pick a favorite album out of the bunch, but it might still be too soon to determine. Plus some of the albums are so vastly different that it's difficult to compare. How about I pick my favorite album of each decade, instead? Okay, here we go:

Favorite 80s Madonna Album: Like a Virgin

Yeah, I know I said I didn't like it as much as her debut album in this very blog, but that was only my initial reaction. I have since grown to love this album so much more. Not only was my initial reaction of this album based on the original release that didn't include "Into the Groove," and not only do the songs "Like a Virgin" and "Material Girl" hit even harder than the hits from her debut album, but songs like "Shoo-Bee-Doo" that I didn't even make note of above have grown on me immensely since my first listen.

Favorite 90s Madonna Album: Ray of Light

Madonna in 1987, just because it's a nice photo

It was pretty much between this and Erotica, which are similar in as many ways as they are different. In the end, Ray of Light edges forward with a few more songs that stand out well on their own rather than relying on the tone of the rest of the album to hold up.

Really though, the best Madonna album of the 90s is the With Honors soundtrack, because her one and only song on it "I'll Remember" is better than everything else she put out that decade combined, and it might still be my all-time favorite song of hers.

Favorite 2000s Madonna Album: Music

This pick was easy. Tracks like "Don't Tell Me," "What It Feels Like for a Girl," and "Music" are the highlights, but everything on this album is catchy, unique, and fun.

Favorite 2010s Madonna Album: Rebel Heart

While this is the only Madonna album of the 2010s that I actually like, I want to make it clear that I like it very, very much. In fact, not only is it my favorite of the decade, but I think it's in my top five favorite Madonna albums overall as well. This is the album that reassures me that, while she might not always make music that appeals to me and she might even stumble overall from time to time, Madonna's not done making great music.

Now if you'll excuse me, I have so much other music to catch up on.
-Ryan