Madonna Louise Ciccone, like Prince and Michael Jackson, was born in 1958, and in the mid-’80s fulfilled her destiny as part of the holy triumvirate of MTV-era pop stars. Of those three legends, Madonna is the only one still alive and filling arenas around the world, performing an astonishing catalog of hits ranging from “Holiday” and “Like a Prayer” to “Vogue” and “Music.” In 2012, she surpassed Elvis Presley and the Beatles with a record 38 Top 10 singles on the Billboard Hot 100 (a record that has since been shattered by Drake, when Billboard’s chart rules changed in the streaming era).
New York, 1984. (Credit: Michael Putland/Getty Images)
While she’s reinvented her sound and image countless times to survive in the rapidly changing pop ecosystem, few A-list singers have shared more of their inner life and personal convictions on record than Madonna. From a thorough inventory of her sexual appetites and ideas about freedom of expression, to motherhood and a personal evolution in her political and spiritual beliefs, Madonna’s albums trace her journey via a world-conquering arsenal of hooks and beats. She’s the Queen of Pop, but she’s also as much a human being and an auteur as any of her contemporaries who are less defined by their commercial ambitions.
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Madonna’s sophomore album Like a Virgin was released on November 12, 1984. The diamond-certified album is her best-selling album (not counting compilations), but is it her very best?
16. I’m Breathless (1990)
Is it possible for someone’s worst album to contain arguably their best single? If any artist with a large catalog has managed that unlikely feat, it’s Madonna. “Vogue,” her deathless dancefloor killer that paid tribute to both New York ballroom culture and old-school Hollywood glamour, appeared on I’m Breathless, the companion album for her role in Warren Beatty’s Dick Tracy. In character as Breathless Mahoney on a series of painfully corny pastiches of swingin’ ’30s jazz, I’m Breathless is barely listenable outside of the big single at the end. Yes, even the three songs written by musical theater legend Stephen Sondheim, one of which won an Oscar.
15. MDNA (2012)
The album title MDNA is classic Madonna – cleverly tying the name for ecstasy that was synonymous with rave culture, MDMA, to her own name. Unfortunately, the music on MDNA is not classic Madonna. The single “Give Me All Your Luvin’” with Nicki Minaj and M.I.A. was Madge’s last Top 10 hit in America. If the song is remembered at all, though, it’s remembered for her Super Bowl halftime show performance, and the tedious controversy over M.I.A. holding up her middle finger during the broadcast. Longtime collaborator William Orbit and an array of then-current hitmakers like Martin Solveig and Julien Jabre try to return Madonna to the Eurodance zeitgeist, but the album is full of poorly aged flourishes like the dubstep drop on “Gang Bang.” Madonna herself is the main problem, though, with blank, pallid vocals that drain songs like “Superstar” of any vitality. Only “I’m A Sinner” is half as fun as Madonna wants it to be, but the album’s best moments are the quieter tracks at the end. “Madonna’s 12th album is the product of both a merger and a divorce, but as much as the singer attempts to milk the latter event for pathos over the course of its 16 tracks, the tone is mostly set by corporate dealmaking,” Matthew Perpetua wrote in the Pitchfork review of MDNA.
14. Hard Candy (2008)
The Virginia Beach producers Timbaland and Pharrell Williams completely changed the sound of mainstream hip-hop R&B around the turn of the millennium. By 2008, both had done most of their best work and were in a bit of a creative rut, but they were still a relatively hip and fresh choice to helm Madonna’s 11th album. Hard Candy is just about the only Madonna album where it truly feels like she’s just riding the wave of her collaborators and adding as little of her own personality as possible. It sounds like a batch of outtakes by Justin Timberlake, who co-wrote five songs and appears on the empty spectacle of a lead single, “4 Minutes.”
13. Madame X (2019)
The guests on Madonna’s most recent album are a mix of southern rappers (Quavo and Swae Lee) and Latin pop stars (Maluma and Anitta). Really, though, Madame X feels like a sequel to one of her most divisive albums, 2003’s American Life, with lots of earnest social commentary sung through a vocoder over icy Mirwais productions. At one point on “Dark Ballet,” Madonna does a spoken word rant about Supreme hoodies over a buzzing synth interpolation of Tchaikovsky’s Nutcracker score. It’s an ambitious and broodingly atmospheric album, but not necessarily a good one.
12. Evita (1996)
Alan Parker’s big screen adaptation of Tim Rice and Andrew Lloyd Weber’s 1978 musical about Eva Perón is the biggest challenge Madonna has ever undertaken as an actress or a vocalist. Madonna’s performance won a Golden Globe, Rice and Weber’s new song for the film “You Must Love Me” won an Oscar, and Evita was a box office success. These days, though, Evita feels like a minor footnote in Madonna’s legacy, with “Don’t Cry For Me Argentina” briefly featured in a medley with “La Isla Bonita” on her latest tour. Parts of the soundtrack album have aged well, and you can easily imagine “Buenos Aires” being dropped into one of her pop albums effectively, but it’s not quite essential listening for musical theater fans or Madonna fans. “Madonna’s voice is pretty in this context, but as bland and milquetoast as can be, thin and limited in range in a role and in music that demands the ability to really sing,” Margaret Moser wrote in the Austin Chronicle review of Evita.
11. Rebel Heart (2015)
Rebel Heart has the same shortcomings as most other late-period Madonna albums, including forced attempts to be provocative, and seemingly random celebrity guests (Chance the Rapper and Mike Tyson, on the same song no less). It’s wrapped up in a more appealing package, though, with noisy, clubby tracks like “Devil Pray” and “Ghosttown.” You still might want to skip past the album’s most popular song and most desperate attempt at a viral moment, “Bitch I’m Madonna.”
10. American Life (2003)
The first album Madonna made after 9/11 was the most explicitly political record of her career, a world-famous celebrity taking a step back and rethinking her relationship with fame and the American dream. American Life’s title track and lead single was panned for Madonna’s heavy-handed rap verse, and at the time it was her lowest-selling album. Madonna and French producer Mirwais Ahmadzai expanded on the sound of her far more successful previous album Music, though, combining acoustic guitars with harsh electroclash production in novel ways on “Intervention” and “Love Profusion.” Madonna’s underrated James Bond theme “Die Another Day” sounds even better in the context of American Life, a dark and strange experiment willfully wedged into a massive franchise.
9. True Blue (1986)
Madonna hung out with the Jacksons on the Victory Tour and hired the keyboardist from their band, Patrick Leonard, who’d become her primary producer and co-writer for the next decade, starting with True Blue. It was the first album Madonna released as an established superstar, and the first two singles, “Live to Tell” and “Papa Don’t Preach,” clearly telegraph her intentions to shed her “boy toy” image and be taken more seriously. It’s by far the least fun of Madonna’s ’80s albums, but it does lighten up at times, particularly on “Open Your Heart” and the standout deep cut “White Heat.” “Singing better than ever, Madonna stakes her claim as the pop poet of lower-middle-class America,” Davitt Sigerson wrote in the Rolling Stone review of True Blue.
8. Music (2000)
Cult singer-songwriter Joe Henry began releasing acclaimed but low-selling albums in 1986, and a year later married Madonna’s sister, Melanie Ciccone. Henry and his famous sister-in-law collaborated for the first time on a Vic Chesnutt tribute album in 1996. It wasn’t until 2000, though, that they co-wrote a song, “Don’t Tell Me,” an innovative collision of country and electronic music that became a Top 10 hit. Madonna reunited with William Orbit for three songs on Music that continue in the vein of Ray of Light, but the more intriguing and commercially successful half of the album came from Mirwais. His halting, blippy aesthetic was like a shock to the system when “Music” hit the American charts, and deep cuts like “Impressive Instant” take that sound to even weirder and more entertaining extremes. “It’s the first Madonna record in years that feels as effortless as the dance-pop of her Ciccone youth,” Alex Pappademas wrote in the SPIN review of Music.
7. Bedtime Stories (1994)
After Erotica, her book Sex, and an expletive-laden interview with David Letterman, the media consensus in 1994 was that Madonna had gone too far as a provocateur and was on the decline. Madonna’s official response on the confrontational Bedtime Stories track “Human Nature” was, simply, “I’m not sorry.” That song, however, was released as the fourth single from the album, after songs like the ballad “Take a Bow” had returned to Madonna to the top of the charts and succeeded in softening her image. Working with producers like Dallas Austin (TLC, Boyz II Men) and Dave Hall (Mary J. Blige, Mariah Carey), Madonna used the sound of contemporary R&B not to sound hip and youthful, but as a vehicle to sing more subtly seductive midtempo songs, a brief but effective detour in her career.
6. Confessions on a Dance Floor (2005)
ABBA were probably the purest personification of pop music before Madonna, so it’s fitting that one of the best hits of the second half of Madonna’s career, “Hung Up,” is built on a sample of the Swedish quartet’s “Gimme! Gimme! Gimme!” Madonna had never been in greater need of a comeback than after American Life, and the return to her disco roots on Confessions of a Dance Floor was the exact right choice at the right time. British producer Stuart Price was a fast-rising star after his acclaimed remixes for artists like the Killers and No Doubt, and his propulsive, dramatic sound matched Madonna’s songs like a modern Giorgio Moroder and Donna Summer. One of the best songs on Confessions on a Dance Floor was called “Forbidden Love,” which was also the case on Bedtime Stories, though they were completely different songs. It does feel appropriate, though, that Madonna of all people would have two songs called “Forbidden Love,” doesn’t it?
5. Madonna (1983)
It may seem strange now to suggest that a superstar synonymous with MTV may have initially been marketed as an anonymous, racially ambiguous voice. When Sire Records issued Madonna’s debut single “Everybody” without her picture on the sleeve, though, R&B and dance DJs played the catchy confection without necessarily having any idea what she looked like. “Many are surprised to learn she’s not black but a green-eyed white blonde,” noted an early profile in the magazine Island. Madonna and her boyfriend John “Jellybean” Benitez were just a couple of 24-year-old club kids when they put together an album full of irresistible smashes like “Holiday” and “Lucky Star” that would slowly, smoothly sail up the charts and eventually sell five million copies, launching an icon.
4. Ray of Light (1998)
By 1998, “electronica” had already experienced a semi-successful wave of American music industry hype, of which Madonna was surely aware—after all, her label, Maverick, released the Prodigy’s The Fat of the Land. Ray of Light arrived after that wave had crested, though, feeling like a singular work from a superstar who’d settled down, had a kid, and gotten really into Kabbalah and yoga. Although the title track and “Sky Fits Heaven” offer four-on-the-floor dance beats, most of William Orbit’s tracks on Ray of Light are densely textured takes on trip-hop and other downtempo styles, giving Madonna a chance to embrace a wider musical spectrum in addition to the album’s rich emotional spectrum.
3. Like a Virgin (1984)
If Madonna’s sleeper hit debut proved that disco could still sell as long as you didn’t use the D-word, that point was made even more plainly when she linked up with Chic’s Nile Rodgers for the album that would send her career into the stratosphere. Like a Virgin doesn’t always get mentioned alongside Thriller and Purple Rain as a coronating moment of ’80s pop supremacy, but it should be. The title track and “Material Girl” are the brazen mission statements that launched the phenomenon, but there’s bubblegum perfection even in less consequential deep cuts like “Shoo-Bee-Doo” and “Over and Over.”
2. Erotica (1992)
Given the chart-topping success of her embrace of house music on “Vogue” and the envelope-pushing sexuality of “Justify My Love,” Madonna had reason to expect Erotica to be a hit. Even in the face of a mounting backlash, she was too big to fail, and the album still went multiplatinum in America and did better abroad. Still, Erotica is the cult classic of her peak period, and whether they knew it or not, Madonna and Shep Pettibone made “Deeper and Deeper” and “Words” for the deep house faithful, not the masses. “The singer doesn’t have great pipes, but because she’s too hip to belt (this time), she doesn’t need them. She’s in control, all understated presence and impersonal personality,” Robert Christgau wrote in the Village Voice review of Erotica.
1. Like A Prayer (1989)
Madonna has seldom held back from speaking her mind in her music, but she probably had more baggage to unload on Like a Prayer than any other album, whether the subject was Catholicism, her relationship with her father, or her divorce from Sean Penn. The album’s title track, a singular masterpiece that finds the gravitas she was searching for on True Blue, features some brief uncredited guitar shredding by one of Madonna’s few peers, Prince. Prince also shows up fully credited on “Love Song,” a great and relatively unheralded duet by two of the most famous musicians on the planet. From the wrenching, autobiographical “Till Death Do Us Part” to the brassy, empowering “Express Yourself,” Madonna emerged from the end of her first marriage more sure than ever of her identity and her message to the world.
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