
POP CULTURE CONFESSIONAL …For some, this has been the summer of The Odyssey or of Spider-Man: Brand New Day, but for others of us, we can’t get enough of Madonna’s Confessions II. Madonna is my favorite … IYKYN … her music has literally soundtracked my life. What you might not know is that it wasn’t always this way.
I spent a summer in Japan in 1990. Back then, my love of comic books overtook all things. I bought a cassette copy of Madonna’s Dick Tracy-inspired I’m Breathless album from a street vendor in Tokyo, so I could have some music of home. It was only THEN that she became my totem and safe harbor.

With that album, all present and future loves converged: super heroes, Sondheim, and Madonna. And I never looked back. With this in mind, and alongside my present obsession with Madonna’s latest offering, I have been thinking about her studio albums all summer … 36 (!) summers after I bought that cassette of I’m Breathless which I still own and treasure. I have been reflecting on how her voice of independence and joy, of inclusion and, well, feistiness continues to impact and inform my worldview.
Soooo, here is my ranking of her studio albums … a list for which no one asked.
- I’m Breathless … see above … most people feel this isn’t a proper studio album, rather a soundtrack. I disagree. First, “Vogue.” Second, it may be her most fully realized, thematic offering. Utter fun. And a total left turn as only she could offer.
- Erotica … my sophomore year of college … still finding myself. Here comes this icy yet heartfelt, percolating indictment of American puritanical hypocrisy. I’m Breathless comforted my homesick soul. Erotica radicalized me.
- Confessions II … the summer of our discontent. Here she comes again, bringing her trademark (and healing) brew of intoxicating rhythms, honesty, critique, silliness, and provocation. Just when we all needed it most.
- American Life … many artists were low key canceled in the awkward oughts, daring to criticize the fraught post-9/11 moment for what we all so clearly now see that it was. Remember this assessment 25 years from the fraught moment in which we now find ourselves …
- Madame X … I love it when pop stars get deliriously weird. ‘Nuff said.
- Ray of Light … earth goddess meets Studio 54, post-Cobain. Per usual, no one saw this coming.
- Bedtime Stories … her Sex book apology tour was actually a hidden middle finger to the critics who tried to silence her, wrapped in the gauzy bubble wrap of mid-90s R&B. And Bjork.
- Like a Prayer … seminal work. Should be my #1. Isn’t. But … “Express Yourself,” “Oh Father,” “Dear Jessie,” “Till Death Do Us Part,” “Cherish,” “Keep It Together.” Like a Prayer walked so Confessions II could run. One of two albums on this list scored from my dad’s Columbia House/BMG Record Club memberships.
- Rebel Heart … so many good tracks. SO many tracks. SO many versions. The first time in Madonna history I lost the narrative of what was what. Here at #9 for the brilliant title cut. Inexplicably a song only released on deluxe special wazoo edition 912.
- Madonna … how it all began. “Holiday.” All you need. But if you need more … “Lucky Star” and “Borderline.”
- MDNA … she was divorced, and she was pissed … but she had a Super Bowl halftime to plan. Decisions, decisions.
- Music … this ranking and the next are likely controversial. Perhaps indicative of my chaotic life at the time. As much as I love the title track, “Impresssive Instant,” “Don’t Tell Me” (one of my absolute faves), and “What It Feels Like For a Girl,” I rarely revisit this one.
- Confessions on a Dance Floor … blasphemy, I know. “Hung Up” (which is my ringtone), “Sorry,” “Issac” … all perfection. But perhaps I was alone in feeling this was a safe and uninspired turn after several albums where Madonna signaled she didn’t really care if you liked her anymore. Can’t blame her. Smart move. But not my fave.
- True Blue … lovely, pleasant, boring album. Many hits. I love “Open Your Heart” and “Live to Tell.” I never, ever listen to this. Respect it, but don’t care to hear it. Two of two albums on this list scored from my dad’s Columbia House/BMG Record Club memberships.
- Like a Virgin … second bit of blasphemy. Her Thriller. The moment the world fixed its collective gaze on her. I was being tortured in junior high by girls dressing like her. Picked on by boys twice my size on the bus home as these songs droned on in the background. Perhaps too much pre-pubescent PTSD wrapped up in this album for me. Own it. Will never play it. “Material Girl” and “Dress You Up” notwithstanding.
- Hard Candy.* Ew. Just ew. (*Except “Miles Away” … that song belonged on another, better album. ANY other album.)

Well, that was therapeutic. Even those albums at the bottom of my list I have pretty much committed to memory. I adore Madonna, and I always shall. She has given voice and perspective to so many facets of life for me. She has been both a healing and a motivating force … and for that I am forever grateful.

