Every Madonna Studio Album, Ranked from Worst to Best (Part 3)

I reveal my picks for the Top 5 Madonna studio albums. Which one will rank No. 1?

In this post, I continue my look at every studio album released by Madonna, ranked from worst to best. I’ve already made 10 selections, some of which have surprised at least a few readers. But, as the great Casey Kasem used to say, the countdown doesn’t stop until we get to the top.

Before I reveal my picks for the Top 5 LPs in Madonna’s discography, please click over to Part 1 and Part 2 of this series if you haven’t read those yet. Also, if you’re enjoying this content and want more of it delivered to your inbox by my army of cyborg primates, consider subscribing.

It would mean a lot to them.

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5. Erotica (1992)

Is Erotica the chilliest club record ever made? The by-product of one of the most infamous celebrity temper tantrums of all time? The product of her audience’s increasing willingness to put her in can’t-win pop culture conversations?

All those distinctions can be true simultaneously. For an album that positions itself to be a searing, post-AIDS look at sex and love, it’s one of the least sexy-sounding releases in her repertoire. MTV’s Kurt Loder compared Erotica to an iceberg, and dubious gender politics aside, it’s not a complete misnomer. It’s purposely aloof and relentlessly in your face about it. This version of Madonna wouldn’t go quietly.

What gets lost in the shuffle is how accomplished the actual music is. Buoyed by some exceptional Shep Pettibone production, it’s irresistible in its dark allure. The best-known cuts, like “Rain” and especially “Deeper and Deeper,” challenge you as much as they move you, which is the whole point. Instead of explicit, I prefer to think of Erotica as provocative, asking the listener to open themselves up to the possibilities presented by this specific bent of dance music.

Sadly, this record consistently soars way above the heads of mainstream consumers, often treated as a footnote alongside the even more infamous coffee table book released in the same promotional cycle as this album. While cool to the touch and divorced from Madonna’s more feel-good 80s oeuvre, Erotica merits far more respect than pop music pundits put on its name.

4. True Blue (1986)

True Blue is arguably the most important inflection point in Madonna’s career. The album turned her into a global superstar, topping the charts in a jaw-dropping 28 countries. It’s the first time she infused her lyricism with more mature-sounding themes and production. It’s also my personal favorite Madonna record.

Then why is it only coming in at No. 4? Let’s say the rankings from here on out are separated by the closest of margins.

There are some delightfully cutesy songs on this tracklist. “La Isla Bonita” is a fun bit of kitsch, “True Blue” updates 60s girl group puppy love for 80s radio, and “Open Your Heart” is as breathless a dance-pop song as you’ll find in her catalog. But the more I listen to the album in full, the more drawn I am to the darker cuts. “White Heat” overlays mid-80s synths and hollowed-out vocals with snippets from the James Cagney film of the same name. At the same time, “Live to Tell” is a spectacular ballad that foreshadowed Madonna’s considerable adult contemporary chops.

Even next to all those highlights, the best song on True Blue is the smash hit opener, “Papa Don’t Preach.” I read several hair-brained takedowns of the song before writing this, dismissing it as shameless audience manipulation. What’s funny is how blind critics are to how much Madonna’s working them over, too. Do you think she didn’t know exactly what the reaction would be when pop’s good girl suddenly talked about keeping her baby in front of millions of fans?

I think not.

PS: True Blue also merits a strong recommendation for all the audiophiles out there looking for some of the best-sounding vinyl from the 80s. If you can scoop an original copy of this album somewhere, prepare to be wowed.

3. Confessions on a Dance Floor (2005)

My goodness gracious. Confessions was so, so, so much better than I remembered it being.

It’s fascinating how memories work in that way. Before undertaking this project, I hadn’t sought out this 2005 gem nor thought much about its tracks since it was initially released. The only song that stuck in my mind’s eye was “Hung Up,” and more for its ABBA sample than anything else.

But, since hearing it with a mostly blank slate, it’s been stuck in my rotation almost weekly. Writing sprints, workouts, you name it, Confessions has soundtracked it. Better late than never, I suppose.

If you’re new(ish) to this album, you’ll find a lot in common with more recent pop production that dips one or several toes in the nu-disco pool. Artists like Ariana Grande, Jessie Ware, and so many others owe a creative debt to the groundwork Stuart Price laid with his production work. His sensibilities are simultaneously very worldly while also grounding this LP’s sound in the New York club scene of yesteryear. His instincts are the x-factor that holds everything together.

There’s also a gross but instructive sexism and ageism angle to Confessions’ reputation, with this Pitchfork review serving as a proxy for what was a pretty common opinion. Back then, Madonna’s pivot to nostalgia-based pop aesthetics was seen as a regression into a past self—needlessly so, too. She was seen as somewhat desperate in how she supposedly tried to claw back whatever cachet she had in the 80s.

Now, with the benefit of hindsight, it’s clear she was ahead of her time. Countless pop acts have ripped off the essence of this record in the intervening 20 years, but few, if any, have equaled its wall-to-wall brilliance. From “Get Together” to “How High” and “Isaac,” it’s just one smart choice after another. One certified banger after another.

2. Like a Prayer (1989)

If True Blue was Madonna’s star-making statement, Like a Prayer cemented her as a generational icon. Easily the most recognizable female pop star of the 80s, she capped off an incredible decade with arguably her most vulnerable outing on record.

I wrote in-depth about this record for its 35th anniversary in 2024. Here’s an excerpt of my thoughts from that piece:

“Her songwriting is more mature, yes, but also far more soulful and unflinching than ever […] Touching ballads like ‘Promise to Try’ and ‘Oh Father’ grapple with her mother’s death and domineering male authority figures, respectively. The vocals on both tracks are surprisingly white-knuckled with anxiety, showcasing a courageousness I don’t think Madonna gets enough credit for. She could’ve opted for a more manicured final product, but leaving it in that state speaks volumes about how personal the recordings were. There’s also a Prince duet, ‘Love Song,’ that makes me wish they’d recorded a full-length project together. The chemistry is that good.”

You also have the grandiose title track, a global hit that’s come to encapsulate, fairly or not, Madonna’s reputation as a “courter of controversy.” Between the religious affirmations and deep-rooted paranoia embedded in the lyrics, it’s never been clear to me whether this track actually cements or rejects any reverence for a higher power. Madonna’s relationship with the Catholic church has historically been complicated at best.

At the end of the day, who cares? The most uplifting spiritual moment comes when that giant choir joins in on that second chorus. It remains one of pop music’s most unforgettable mid-song gear shifts.

1. Ray of Light (1998)

Here it is. Gun to my head, discography ranking on the line, Ray of Light is my pick for Madonna’s best album.

The record came on the heels of massive changes in the star’s personal and professional life. She’d become a new mother, begun studying Kabbalah and Hinduism, and coming off the grueling vocal training and shoot for 1996’s Evita. She even scrapped a few songs written with her Bedtime Stories collaborator, Babyface. It was clear she wanted to push her boundaries even further.

According to Orbit, the electronic music veteran who produced all but one track with Madonna, the recording process was as laborious as it was fast-paced. "It took a long time to do the album […] And it wasn't like we were slacking. We actually did have to work fast, and there were many times when we had to move on. One of Madonna's favorite phrases was: 'Don't gild the lily.' In other words, keep it rough, and don't perfect it too much. It's a natural urge for computer buffs to perfect everything because they can, and we were very wary of that.”

The resulting LP is a masterclass in meticulous, lush craftsmanship, bringing together Indian, Moroccan, British, and American influences. When it needs to bring brooding, introspective energy, like on “Swim” and “Nothing Really Matters,” the subdued production helps reveal different dimensions to Madonna’s deeper, more soulful vocal delivery. But, when it needs to throb with uninhibited joy, like on the euphoric title track, Orbit gives her a launching pad fit for the Queen of Pop.

By 1998, Madonna had little left to prove commercially. But, after middling fan and critical reactions to her previous few albums, she sounds like she wanted to get herself to another level creatively. That, for me, is the sign of true greatness—when you dig deeper than you ever have before, even when it’s not expressly asked of you.

This discography ranking was always going to be a close call, but when the chips are down, none of Madonna’s other studio albums top this one.

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Which Madonna record is your favorite? Would you have crowned a different album her best? Sound off in the comments.