The Guide to Getting Into Madonna, Holy Mother of Modern Pop

She's a true original with a decades-deep catalog, so ahead of the release of 'Madame X,' here's a streamlined guide to her restlessly creative and game-changing career.
illustrated by Tara Jacoby

Though Madonna’s been called the “Queen of Pop” for the majority of her 37-year recording career, in a way she’s also strangely underrated. "People have always been trying to silence me for one reason or another, whether it’s that I’m not pretty enough, I don’t sing well enough, I’m not talented enough, I’m not married enough—and now it’s that I’m not young enough," she told British Vogue recently.


But since 1978, when she relocated from Bay City, Michigan to New York with just $35 in her pocket, according to legend, Madonna has insisted on speaking her truth. “I’m tough, I’m ambitious, and I know exactly what I want. If that makes me a bitch, okay,” she famously said in a 1992 People interview. Her ability to adopt different personas and attention-grabbing scandals have been well-documented, even when critics haven’t fully appreciated the creative risks they involve. Her 1992 Sex book remains the only glossy coffee table tome to show a pop superstar simulating S&M and analingus. Because Madonna is a button-pushing figure whose body has been scrutinized as much as her work, her music’s sheer pop brilliance often gets sidelined, too.

Feminist author Germaine Greer claimed in 2006 that Madonna’s real genius lies in marketing, writing, "She has always kept an ear out for whatever was happening on the underground. The trick was to recognize what could be commercialized and to go ahead and do it.” Madonna’s ability to recalibrate cutting-edge culture for a mainstream audience is definitely worth celebrating, but this talent has sometimes led to accusations of cultural appropriation. Her 1990 smash “Vogue” was inspired by the buoyant house tracks and glamorous dance moves of the Harlem ballroom scene. It was a shrewd move, superbly executed with an iconic video, but critics have argued that by name-checking an all-white list of Hollywood icons in her lyrics, Madonna was “erasing voguing’s original context as a creation of queer people of color."


At the same time, Greer’s assessment of Madonna’s skillset feels, well, reductive–to borrow a term that Madonna deployed when asked about perceived musical similarities between her 1989 hit “Express Yourself” and Lady Gaga’s 2011 single “Born This Way.” As co-writer and co-producer of the vast majority of songs she’s released since her 1982 debut single “Everybody,” Madonna has built one of contemporary pop’s most impressive songwriting catalogs. "Someone who you might not think of as the world’s best lyricist is Madonna," Pet Shop Boys' Neil Tennant said last year, "but she always gets the emphasis on the right syllable.” Stuart Price, Madonna’s main collaborator on 2005’s excellent, club-ready album Confessions on a Dance Floor, praised her “inherent understanding of dance music and pop music.”

Confessions is one of three stone-cold classic LPs in Madonna’s oeuvre; the others are 1989’s deeply personal pop masterpiece Like a Prayer and 1998’s forward-thinking electro opus Ray of Light. And her original greatest hits compilation, 1990’s The Immaculate Collection, is as close to flawless as pop music gets. But with Madonna about to drop her 14th studio album, Madame X, which critics are hailing as her most “bizarre” and “daring” ever, it’s the perfect time to reconsider the music that’s made her a pop culture colossus, longtime LGBTQ icon, and the fourth-best-selling artist of all time.


Because her decades-deep catalog can be daunting to navigate, especially outside of those classic albums, we put together a streamlined guide to some of the most enduring moments in her restlessly creative and game-changing career. If you still think Madonna’s kind of overrated after listening to these tracks, then take a tip from Britney Spears. "I'm sorry, but I'd rather meet Madonna than the President of the United States,” the younger pop star wrote in 2004. “Madonna was the first female pop star to take control of every aspect of her career and to take responsibility for creating her image, no matter how much flak she might get."

So you want to get into: Pure Pop Madonna?

This playlist could be longer—much longer. Madonna’s first couple albums yielded the instant-classic hits "Borderline," "Lucky Star," "Material Girl," and "Like a Virgin." "Virgin" is often painted as Madonna’s first scandalous moment, partly because she writhed on the floor in a wedding dress when she performed it at the 1984 VMAs. But I've always found "Borderline" every bit as suggestive, probably because my mom insisted that the lyrics are "really about reaching orgasm, you know." I'll leave you to decide whether you agree with her sex-positive interpretation.

Her third album, 1986’s True Blue, is one of the most enjoyable pop collections of its era, home to the iconic bops "Open Your Heart," "Papa Don’t Preach," and "La Isla Bonita." By this point, Madonna had become known for a certain kind of perky and super-melodic pop tune, but she was already beginning to push its limits: The album's title track is a joyous 60s girl-group homage that she revived on 2015’s Rebel Heart Tour.


Follwing 1989's musically rich and inventive Like a Prayer album, which dazzled listeners with its still-ubiquitous title track as well as feminist rallying cry "Express Yourself," kept churning out pop hooks: Check out the killer chorus on 2005’s "Jump." But many of her career highlights from the 90s onwards saw her delve deeper into dance music and electronica, even when the unshakable choruses kept on coming. Some exceptions are "Secret," a lovely folky number from 1994’s Bedtime Stories; 1999 psychedelic gem "Beautiful Stranger"; and Madame X promo single "Crave," an appealingly hazy collaboration with Rae Sremmurd’s Swae Lee that boasts one of Madonna’s stickiest melodies in years.

Playlist: "Borderline" / "Lucky Star" / "Like a Virgin" / "Material Girl" / "Open Your Heart" / "Papa Don't Preach" / "La Isla Bonita" / "True Blue” / "Who's That Girl" / "Till Death Us Do Part" / "Like a Prayer" / "Express Yourself" / "Cherish" / "Secret" / "Beautiful Stranger" / "Jump" / "Crave"

So you want to get into: Club Queen Madonna?

Deciding whether some Madonna songs are more "pop" or "dance" feels kind of arbitrary. Any wedding DJ will tell you that "Like a Prayer" fills the floor every time, and she's scored a record 46 number-ones on the Billboard Dance Club Songs chart. Quite simply, clubbing is in Madonna's musical DNA: Before she smashed into the mainstream with 1982's "Holiday," she was a regular at legendary New York City nightspot Danceteria, where she persuaded DJ Mark Kamins to play her post-disco debut single "Everybody" and later gave her first ever live performance.


With all this in mind, I've picked 13 Madonna songs that sparkle particularly brightly in a space where communal dancing is possible: the club, say, or your kitchen after a couple glasses of Chardonnay. Recorded for Madonna's first and arguably best movie, Desperately Seeking Susan, 1985's blissful "Into the Groove" almost feels like a manifesto: "Only when I'm dancing can I feel this free," Madonna sings euphorically. A few years later, her early 90s collaborations with DJ/producer Shep Pettibone produced some heady house bangers—you surely know "Vogue," but "Deeper and Deeper" and "Rescue Me" are equally sinewy and thrilling.

It may be more than two decades old, but the title track from 1998's Ray of Light still slaps remarkably hard, and 2005's "Hung Up" remains a masterstroke. Who else but Madonna would think to build a shimmering club banger around an ABBA sample—then persuade the Swedish pop supremos, notoriously protective of their own music, to grant her permission to use it? "Get Together"—a fan favorite from the same album, Confessions on a Dance Floor—even earned a Grammy nomination in the Best Dance Recording category; ace singer-songwriter Shura recently confessed that she jammed it non-stop on a bus from Lima to Buenos Aires.

More recently, 2012's patchy MDNA album produced an underrated EDM thumper in "I'm Addicted," and "Living for Love," from 2015’s messy but sometimes magical Rebel Heart LP, shows Madonna’s unflagging passion for making people move. Co-producer Diplo revealed that he and Madonna went through around 20 different mixes before settling on the housey final version.


Playlist: "Everybody" / "Holiday" / "Into the Groove" / "Vogue" / "Rescue Me" / "Deeper and Deeper" / "Ray of Light" / "Music" / "Hung Up" / "Get Together" / "Celebration" / "I'm Addicted" / "Living for Love"

So you want to get into: Balladeer Madonna?

Madonna is best known for her bangers, but by 1995, she already had enough superior slowies to release a ballads compilation, Something to Remember. "You’ll See," recorded expressly for that album, is so classy and dramatic, it was even covered by Susan Boyle. Yes, really.

While she’s never been a vocal powerhouse like her 80s contemporary Whitney Houston, Madonna demonstrated her ability to carry a ballad early on. In his review of 1986’s True Blue album, AllMusic's Stephen Thomas Erlewine hails "Live to Tell" as a "tremendous ballad that rewrites the rules of adult contemporary crossover." On "Oh Father," from Like a Prayer, Madonna explores her difficult relationship with her dad; on "In This Life," from 1992’s Erotica, she mourns friends and mentors taken by AIDS. "Have you ever watched your best friend die–what for?" she sings, remembering her former roommate Martin Burgoyne, who'd died of the disease six years earlier.

"The Power of Good-Bye" from Ray of Light is simply stunning, and "Nothing Fails," from 2003’s American Life album, is arguably the great Madonna hit that got away. When a gospel choir unexpectedly comes in at the climax, it makes your arm hair stand on end. Fans also love "Joan of Arc" from Rebel Heart, partly because its lyrics are among Madonna's most revealing. "Each time they write a hateful word, dragging my soul into the dirt, I wanna die," she sings, proving that even the Queen of Pop can be vulnerable to criticism.


Playlist: "Crazy for You" / "Live to Tell" / "Oh Father" / "Rain" / "In This Life" / "I'll Remember" / "Take a Bow" / "You'll See" / "The Power of Good-Bye" / "Nothing Fails" / "Miles Away" / "Joan of Arc" / "Ghosttown"

So you want to get into: R&B Diva Madonna?

Madonna has leaned heavily into R&B on two albums: 1994's Bedtime Stories, which contains collaborations with TLC producer Dallas Austin, and 2008's Hard Candy, on which she teamed up with Pharrell Williams and Timbaland. Bedtime Stories is no classic, but "Human Nature" is a fabulously unapologetic clapback to critics who slut-shamed her during the highly sexualized Erotica era. "You punished me for telling you my fantasies / I'm breaking all the rules I didn't make," she seethes.

Hard Candy isn't first-rate Madonna, either: she recruited Timbaland after he’d produced huge hits for Nelly Furtado ("Promiscuous") and Justin Timberlake ("Cry Me a River"), so it felt at the time as though she was chasing pop trends rather than setting them. Still, her own Timberlake duet "4 Minutes" is a worthy hit single, and the daring disco-filter house hybrid "She’s Not Me," co-produced by Pharrell, sounds like a song only Madonna could make. "I Don’t Give A," an electro-funk nugget from 2012's MDNA that features a brilliant Nicki Minaj rap, also works well here. Penned following her 2008 divorce from movie director Guy Ritchee, its rapid-fire lyrics offer a glimpse into Madonna's ridiculously hectic daily schedule as a single mom. "Wake up ex-wife, this is your life," she sings at the start of the song, followed by a shrugging "Lawyers, suck it up—didn’t have a pre-nup" on the second verse. Ouch.


Playlist: "Human Nature" / "Inside of Me" / "4 Minutes" / "Candy Shop" / "She’s Not Me" / "Give It 2 Me" / "I Don’t Give A…"

So you want to get into: Experimental Madonna?

By bookending 1990's The Immaculate Collection with the sensual and poetic trip-hop gem "Justify My Love," Madonna was signaling her desire to push her music in unexpected new directions. And so she did: 1992's Erotica album may have been a relative flop at the time (it "only" went double-platinum in the US), but its seductive and surprisingly downbeat blend of electronica, hip-hop, deep house, and R&B makes it Madonna's most fascinating album. Check out the freaky break-up song "Bye Bye Baby," which smothers Madonna’s vocal in an effect that makes it sound like she's dumping someone in a voicemail. "You fucked it up," she informs him just before hanging up.

Co-written by Björk, who said that the song tapped into "the things I have always wanted to hear [Madonna] say that she's never said," 1994's "Bedtime Story" must have seemed like an anomaly at the time. But in hindsight, the esoteric electro track feels like a dry run for 1998’s Ray of Light. That album’s sublime, swirling lead single "Frozen" would become a global smash, but "Drowned World/Substitute for Love," an ambient pop song where Madonna ponders the price of fame, is equally beguiling.

After Ray of Light, Madonna made two albums (2000’s Music and 2003’s American Life) with French electro wiz Mirwais Ahmadzaï, with whom she would reconnect for Madame X. These contain some of her most challenging and thrilling music: with its glitchy beats and poetic lyrics, "Don’t Tell Me" is a country-pop crossover that sounds like no other country-pop crossover I've ever heard—no wonder Miley Cyrus likes it—and the electro-folk "Hollywood" contains a bracingly strange industrial breakdown.

Madonna's appetite for experimentation hasn’t dissipated: "Bitch I’m Madonna," from 2015's Rebel Heart, is a playful romp produced by Diplo and avant-pop artist SOPHIE. And "Dark Ballet," from Madame X, begins as an ominous piano ballad before incorporating a Tchaikovsky sample. Still, it feels most fitting to end this playlist with 2000's "Impressive Instant," an odd but catchy song about losing yourself on the dance floor, because it melds so many elements of what makes Madonna, well, Madonna. "You’re the one I’ve been waiting for," she purrs over a trippy techno throb. "I don’t even know your name." Oh Madonna, we’ve all been there.

Playlist: "Justify My Love" / "Erotica" / "Bye Bye Baby" / "Frozen" / "Bedtime Story" / "Drowned World/Substitute for Love" / "Don't Tell Me" / "What It Feels Like for a Girl" / "American Life" / "Hollywood" / "Die Another Day" / "Bitch I'm Madonna" / “Dark Ballet” / "Impressive Instant"