12. LIKE A VIRGIN (1984)
After a strong debut, Madonna really exploded with Like a Virgin. In one year she became the most talked about and most popular singer in the world. This second album gave her her first #1 record and first #1 song (the title track) and three other top 5 hits. It established her as a more serious artist and one that would influence girls around the world through sexual independence and through fashion. It was also with this album that Madonna would begin courting religious controversy. Merging her religious name with sexual imagery in a very in your face way only brought her more attention and more fame.
I’ve never been crazy for this album as a whole. There are too many empty tracks, especially the album closers. ‘Shoo-Bee-Doo,’ ‘Pretender’ and ‘Stay’ just don’t live up to the earlier tracks. I’m not even a big fan of ‘Like a Virgin’ itself. Where my love truly lies on this album is with ‘Material Girl,’ ‘Dress You Up’ and the song that should have been a massive hit, ‘Over and Over.’ Thankfully that song found new life on the remix album You Can Dance. It’s one of her most buoyant, fun dance songs.
Hits: Like a Virgin (first #1 song), Material Girl (#2), Angel (#5), Dress You Up (#5)
Should Have Been a Hit: Over and Over
11. MADONNA (1983)
The album that started it all. After toiling in clubs for years to get airplay, Madonna’s eponymous album arrived with not too much fanfare at first. ‘Everybody’ was released as a single far ahead of the album release to generate anticipation but it failed to make much of an impact on Billboard other than the dance charts. ‘Burning Up,’ what I consider to be one of her best songs, was her 2nd single and it also went nowhere. It’s rock guitar combined with a dance groove was a clear descendant of Blondie and the video literally put Madonna in the driver’s seat of the song.
Ultimately, it was ‘Holiday’ that would be her first charting single, breaking into the top 20. It’s now a staple of her concerts and is one of the most popular dance songs of all time. Its performance paved the way for ‘Lucky Star,’ her first top 5 song and for ‘Borderline,’ another top 10 hit. ‘I Know It’ has a Brenda Lee bubble-gum pop energy that’s infectious and could have been a hit.
Hits: Holiday (#16), Lucky Star (#4), Borderline (#10)
Should Have Been a Hit: Burning Up, Think of Me
10. HARD CANDY (2008)
Let’s just this out of the way; ‘Candy Shop’ is terrible. Never should have been the lead off song for the album because although Madonna claims, “my sugar is sweet…” this leaves a bad taste in my mouth and I usually skip right over it. In her first album post-divorce from Guy Ritchie (and father of Rocco), Madonna digs in with ‘Miles Away,’ an exploration on long-distance love in its successes and failures.
‘She’s Not Me,’ about a copycat trying to take her place could be perceived as a woman attempting to take her man or her place in pop music, or both. Her collaboration with Justin Timberlake, ‘4 Minutes (To Save the World)’ hit #3 and became her 37th top 40 hit, breaking Elvis Presley’s record and putting Madonna on top, where she still reigns today.
Hits: 4 Minutes (To Save the World) featuring Justin Timberlake and Timbaland (#3)
Should Have Been a Hit: Miles Away, She’s Not Me
09. AMERICAN LIFE (2003)
American Life remains the lowest selling album of Madonna’s career in the U.S. and one of her most critically maligned as well. Yes, there are some real stinkers on the album in ‘Hollywood’ and ‘I’m So Stupid.’ ‘Mother and Father’ finds her dipping into the well of parent issues but this time with diminishing results. She did a much better examination of her family life back in 1989 with ‘Promise to Try’ and ‘Oh Father’ from Like a Prayer. And yes, the ill-advised decision to rap in the middle of the title lead single didn’t do her any favors. Part of the problem, I think, is that half of the songs sound like they should have been on ‘Music’ and butted up against the overly electronic elements of some of the songs makes the album a bit non-cohesive.
But, within the album, if you dig a little deeper, you’ll see she does too. ‘Love Profusion’ is melodic and dreamy, ‘X-Static Process’ is a superb example of intelligent self-examination and ‘Nothing Fails’ finds some roots in ‘Like a Prayer’ that work, where ‘Mother and Father’ didn’t. Interestingly, the amount of over-production that hobbles the album’s worst songs are exactly what makes the only hit, ‘Die Another Day’ exceptional. Yes, it didn’t need the spoken word elements (“Sigmund Freud, analyze this…”) but it’s such an aggressively, in your face jam that it’s hard to not move to it.
Hits: Die Another Day (#8)
Should Have Been a Hit: Love Profusion, X-Static Process, Nothing Fails
08. TRUE BLUE (1986)
Building on the strength of Like a Virgin, True Blue found Madonna with her best selling album (topping charts in 28 countries) and with the most Top 5 singles of her career (including three #1s). After finding ballad success with the #1 ‘Crazy For You’ in 1985 (from the film Vision Quest), the first single from True Blue, ‘Live to Tell’ (also featured in the film At Close Range, starring then husband Sean Penn) was a massive success. With stripped down vocals and a video of her conservatively dressed and sans most makeup, it was an incredible departure for Madonna and a great example of how she is always able to be one step ahead of people thinking they know who she is.
It was the second single, ‘Papa Don’t Preach,’ about teenage pregnancy, that turned that back around and established the beginning of Madonna’s courtship with religious controversy. It was a place she’s found residency in all decades of her career so far. The title single, an homage to 60s girl groups is often written off as too much of a trifle in the face of songs on the album dealing with meatier issues but it’s that type of flight of fancy that keeps the album from being too issue-heavy.
That said, the album isn’t without its flubs. ‘White Heat’ (which almost feels like a precursor to her Dick Tracy-inspire album, I’m Breathless) and ‘Jimmy Jimmy’ are pretty flimsy and go nowhere. Although ‘La Isla Bonita’ was a big hit for her and is a popular song in her canon, I’ve never been a fan. In fact, I haven’t liked any of her forays into Spanish songs and subjects.
Hits: Live to Tell (#1), Papa Don’t Preach (#1), True Blue (#3), Open Your Heart (#1), La Isla Bonita (#4)
Should Have Been a Hit: Where’s the Party
07. CONFESSIONS ON A DANCE FLOOR (2005)
After the brutal reception of American Life, Madonna did what she does best, subvert expectations and do something crazy and awesome. Confessions on a Dance Floor was a massive comeback both in sales and critical response. It was a retro throwback of epic proportions, digging its roller skates deep into disco and cemented itself as one of the best dance albums of the decade.
One of the best elements of the album is that there are no breaks between songs. It’s meant to be played continuously through; a true party album. It works incredibly well, with a rhythmic flow that courses through the record from beginning to end. If there’s a sore thumb here it’s ‘I Love New York.’ It’s just a bad song. And not just the line with Madonna complaining that other cities make her “feel like a dork” simply to get a rhyme with New York. It’s arguably the worst song of her career. ‘How High’ comes close to being another stinker with its recycled ‘poor me, isn’t fame a bitch’ theme that Madonna has done before, with better results. Still, even with those two the album is a giant success for her when it simply cuts free of misguided metaphors and just allows itself to be a consummate dance record.
‘Future Lovers’ has Madonna instructing her listeners “forget your problems, administration, bills and loans” in this yoga meets disco slow jam. The amazing ‘Isaac,’ which features vocalist Yitzhak Sinwani, who sings portions of the Yemenite Hebrew poem Im Nin’alu, has a tick tock beat of a metronome. It’s the opposite end of the spectrum of Ray of Light’s ‘Shanti Ashtangi’ in terms of incorporating scripture into a song successfully. ‘Forbidden Love’ is a perfect example of how Madonna is able to create simple, perfect dance/pop yet I can still call it some of her best work.
Despite only reaping a single hit from the album, that song, “Hung Up,” still holds the world record for being #1 in the most countries (41) at the same time. Ironically, the U.S. was not (it peaked at #7) and it spoke to Madonna’s continued success worldwide.
Hits: Hung Up (#7)
Should Have Been a Hit: Forbidden Love, Sorry
06. MUSIC (2000)
AKA the album in which Madonna learns guitar. After the huge success of Ray of Light and its heavy bent on electronica, Music continues that trend (sometimes to a fault) with her most electronic and auto-tuned record to date, mostly thanks to producers William Orbit, Mirwais Ahmadzaï and often mixes in strumming guitar. It works spectacularly well on ‘Don’t Tell Me’ and ‘Gone,’ the former of which saw Madonna reinventing herself as a cowgirl.
The album was created in between her relationships with Carlos Leon, the father of her first child, Lourdes, and Guy Ritchie, the father of her second child, Rocco. There is a fascinating push-and-pull at work with songs that are cynical about love and self-worth (‘Nobody’s Perfect) to ones that celebrate finding it (‘I Deserve It’). The opening title track, her last #1 song, starts off with a bump and bass meets techno flair and that follows through into ‘Impressive Instant’ and ‘Runaway Lover’ and was one of her catchiest songs since ‘Holiday.’ One of the more elusive yet fascinating tracks is ‘Paradise (Not for Me).’ It’s Madonna’s most experimental since ‘Bedtime Story,’ and is more spoken than sung and vocoded to within an inch of her life. But the arrangement is like this wild hybrid of Giorgio Mororder and Angelo Badalamenti that is pretty intoxicating.
The standout track on the album though is ‘What It Feels Like For a Girl.’ It’s the song that merges the two points and men in her life. It demands the respect that she feels she (and women at large) doesn’t get, but ultimately doesn’t need from men, so she supplies the empowerment herself. The accompanying video, directed by Ritchie and featuring Madonna and an old woman going on a crime spree, was banned from most North American television for being too graphic and violent, the ultimate hypocrisy and irony. And, all shade aside, Madonna has never been the best songwriter but this collaboration with Guy Sigsworth is a high point. “Hands that rest on jutting hips repenting” might be my single favorite lyric of Madonna’s career. There is something so viscerally visual about the image, I practically see it in slow motion and feel the weight of it. It’s a true masterpiece on an album full of great pieces.
Hits: Music (last #1 song), Don’t Tell Me (#4)
Should Have Been a Hit: What It Feel Like for a Girl, I Deserve It, Impressive Instant
05. MDNA (2012)
Like American Life, MDNA was one of Madonna’s worst sellers yet still packed with so many brilliant songs. Given the platform of the Superbowl halftime show in 2012, the lead single ‘Give Me All Your Luvin’’ and its football-themed video were simply too silly and superficial for some (it’s a fun song, not much more) to allow anything else become a hit. That single struggled to make the top 10 and fell off immediately after it did. In fact, the album’s 2nd week sales rank in the top 3 all-time 1st to 2nd weeks drops, not a record one wants to have.
It doesn’t help that radio has completely shunned Madonna at this stage in her career. Ageism seems like a pretty clear antagonist in this drama but Madonna, like Cher and Barbra Streisand know full well that the money isn’t in album sales, it’s in touring. Madonna consistently ranks at the top of Forbes earning charts when she mounts a big tour in support of a current album and the tour for MDNA was no exception. It became the second highest grossing tour by a female artist in history. What’s #1, you ask? Yep, Madonna. Her Sticky & Sweet tour reigns as the best selling tour ever.
But, back to the album. Working with a large stable of producers including Guy Oseary, Martin Solveig, William Orbit and the Benassi Brothers, the album runs the gamut of danceteria fun, still unresolved heartbreak from her divorce from Guy Ritchie and lots and lots of partying. The thumping beats of ‘Turn Up the Radio’ should have been a massive summer single. The songs ‘Love Spent’ and ‘I Fucked Up’ continue to detail the demise of her marriage but this include her own culpability in it. They’re both brilliant. ‘Gang Bang’ and ‘I’m Addicted’ are aggressive and in our face and some of Madonna’s best work.’Falling Free’ does what Madonna does best for me, take a ballad, which I notoriously don’t like, and turn out something nearly perfect. In fact, the album as a whole is one of her best, which is why it’s ranked so high.
Hits: Give Me All Your Luvin’ (#10)
Should Have Been a Hit: Turn Up the Radio, Love Spent, I’m Addicted
04. LIKE A PRAYER (1989)
Coming off the heels of the massive success of True Blue and the Who’s That Girl soundtrack, Like a Prayer was also a giant hit for Madonna and was the first album in which she subverted some of her more superficial song subjects for serious (and sometimes controversial) topics like religion, her failed marriage to Sean Penn (‘Til Death Do Us Part’) and her relationships with her father (‘Oh Father’) and deceased mother (‘Promise To Try’) in order to stake a claim at being a more serious artist.
Jumping off the religious controversy from True Blue’s ‘Papa Don’t Preach,’ the title song from Like a Prayer (and its accompanying video) found her at the center of a massive controversy. In combining sexuality with religion, including getting rather intimate with a black Jesus and dancing in front of a field of burning crosses, the controversy caused Pepsi to pull a spot with her. Growing up in a strict Catholic household gave Madonna the source of her ammunition and redemption for this album. But for Madonna, her battle with religion was always one of searching for answers and understanding, not simply bashing it and that struggle is threaded through the entire album.
But, the album is still peppered with gorgeous confections of empowerment in ‘Express Yourself,’ with its iconic, Metropolis-inspired David Fincher-directed video and the bubbly ‘Cherish,’ which would have felt right at home as a track on True Blue. Just as vital are the Sly and the Family Stone-esque ‘Keep It Together’ and ‘Dear Jessie,’ one of her most underrated songs that sometimes feels like a pre-motherhood lullaby. She also makes room for a brilliant collaboration with Prince in ‘Love Song’ (who ended up playing guitar on three tracks) and the cheeky humor of the closing single ‘Act of Contrition’ (“…what do you mean it’s not in the computer?!).
Hits: Like a Prayer (#1), Express Yourself (#2), Cherish (#2), Keep It Together (#8), Oh Father (#20)
Should Have Been a Hit: Dear Jessie, Promise to Try
03. BEDTIME STORIES (1994)
After the deep disco of Erotica and the intense blowback of its overt sexuality (and that book), Madonna gets her groove on with her most soul and R&B inspired album to date. Interestingly, Madonna’s earlier work has always been a hit on R&B stations but with Bedtime Stories she eschews a lot of her dance and pop for swerve and sway funk. The opening tracks ‘Survival’ and ‘Secret’ are Spanish-Harlem infused bits of new jack swing that perfectly set up the album. ‘Inside of Me’ is a sultry slow-jam like it could have come off a Janet Jackson record.
The pain of the blowback from her “Sex” book is front and center in ‘Human Nature,’ a stinging retort of the criticism she took for it (“Oops, I didn’t know I couldn’t talk about sex…”) and one of the first times she addresses her critics in song. It and the video are little masterpieces.
The album, for its modest commercial success, features her longest running #1 song ever in ‘Take a Bow,’ one of her many ballads to reach the top spot. The only song not written or co-written by Madonna was ‘Bedtime Story.’ The song, co-written by Bjork, deviated from the rest of the album (despite carrying its title) with a more electronic, esoteric feel both in lyrics and musical arrangement. It wasn’t a big hit for her as it was probably too much of a departure for her fans.
Hits: Secret (#3), Take a Bow (longest running #1 at 7 weeks)
Should Have Been a Hit: Human Nature, I’d Rather Be Your Lover, Inside of Me, Survival
02. EROTICA (1992)
Is this possibly Madonna’s most underrated album ever? Cultivating the persona of Dita, Madonna transformed herself into a disco dominatrix for the title track (and controversial video) and explored levels of sexuality and S&M she began with 1990’s ‘Justify My Love.’
So much happened in the three years between the releases of Like a Prayer and Erotica that it’s almost as if two different people made these albums. Up to Like a Prayer, Madonna’s take on sexuality was largely playful and come hither. Thinking back to her MTV Video Music Awards performance of ‘Like a Virgin,’ rolling around on the floor in that wedding dress, it certainly seems tame when you stack it up against the banned video for ‘Justify My Love,’ the release of her concert tour movie Truth or Dare (a massive hit) in 1990 and her extraordinarily controversial NSFW coffee table book, “Sex,” released as a simultaneous orgasm along with the album, Erotica.
Track after track you’ll find thumping disco beats in ‘Deeper and Deeper,’ one of her best dance songs ever, gorgeous melancholy and remorse in ‘Bad Girl,’ and cunningly clever coyness about the art of female oral pleasure in ‘Where Life Begins’ and the revenge piece ‘Thief of Hearts.’
Hits: Erotica (#3), Deeper and Deeper (#7), Rain (#14)
Should Have Been a Hit: Bad Girl, Thief of Hearts
01. RAY OF LIGHT (1998)
A comeback of epic proportion and an album that reflects an enormous amount of growth and life change for Madonna, Ray of Light could be her career-defining work. Coming off the heels of her success with Evita (for which she took singing lessons for the first time in her career, no jokes, bitches), delved into Kabbalism for spiritual guidance and, most importantly, the birth of her first child, Lourdes. While primarily a pop album, it’s infusion of dance, electronica (the influence of producer William Orbit) as well as rock, trance and classical give Ray of Light a bigger, more evolved flavor all while remaining surprisingly cohesive.
From the opening double song ‘Drowned World/Substitute for Love,’ where Madonna examines her place in celebrity, the price of it and the importance of it in the face of being a new mother to the high-tempo fun of the title single to the richly layered arrangements of ‘Frozen’ and ‘Power of Good-bye,’ Ray of Light exists in a place unlike anything she had done before. The only misstep is the sing-chant ‘Shanti/Ashtangi.’ Taken directly from Shankaracharya in traditional Sanskrit, it may be speak directly to Madonna’s spiritual place and time but for the listener it sounds like background music at an Indian restaurant. Reflection on family ends the album with the ode to her daughter in ‘Little Star,’ a maternal piece that sounds like a rhythmic lullaby and the somber ‘Mer Girl,’ about (again) the death of her mother. This time though with lyrics of depth and creativity that her life experience has brought her.
Not just one of her biggest commercial hits, Ray of Light remains her biggest critical hit to date and the album also gave Madonna the Grammy love her career had been lacking. It garnered her first Album of the Year and Record of the Year nominations and won Pop Album, Short Form Video (‘Ray of Light’), Dance Recording (‘Ray of Light’) and Package Recording.
Hits: Ray of Light (#5), Frozen (#2), The Power of Good-bye (#11)
Should Have Been a Hit: Drowned World/Substitute for Love, Nothing Really Matters