How Madonna Became The Queen Of Pop & Reinvention, From Her 'Boy Toy' Era To The Celebration Tour
As Madonna fans eagerly await the start of her highly anticipated The Celebration Tour, take a look back at the icon's four-decade legacy that changed pop music forever.
Seconds after making her television debut on American Bandstand in early 1984, Madonna announced her plans to "rule the world."
Nearly 40 years later, she's done just that: Selling 300 million albums worldwide, Madonna is one of the best-selling artists of all time. Her 14 studio albums have spawned 12 No. 1s and 63 top 10 hits on the Billboard Hot 100, and she earned a spot in the Rock & Roll Hall of Fame in 2008. But just her nickname alone proves she achieved her goal: the Queen of Pop.
Madonna's legacy is more than her music, too. The seven-time GRAMMY-winner has empowered several generations to own their sexuality and call their own shots; she dared to be different and bending the rules on and off stage, particularly with the merging of sexual freedom and religion. Her fearlessness helped open doors for individuality in pop music and beyond, becoming a star that didn't just rule the world — she changed culture.
As Madonna's self-titled debut LP turns 40 on July 27, we are revisiting the most groundbreaking, exhilarating, and gasp-worthy moments of her extraordinary career.
On July 13 1985, Madonna performed at the Live Aid benefit concert at JFK Stadium, Philadelphia, PA.
The '80s Reign
"Everybody" and "Burning Up," the first two singles off Madonna's 1983 eponymous solo debut, were instantaneous dance hits but failed to crack the Hot 100. Rooted in disco, "Holiday" not only became Madonna's first Hot 100 entry at No. 16, but it also topped the Dance Club Songs chart — her first of 50, a record no other artist holds to this day. It also spawned even bigger hits "Lucky Star" and "Borderline," which reached No. 4 and No. 10 on the Hot 100, respectively.
As "Borderline" climbed the charts, Madonna enlisted the legendary Nile Rogers to craft what would become the best-selling album of her career: Like a Virgin.
Selling over 21 million copies worldwide, 1984's Like a Virgin proved Madonna wasn't just another flash in the pan with a long string of hits, including "Material Girl," "Dress You Up," and her first chart-topper, "Like a Virgin." But her sexual assertiveness is what made the era truly iconic. The sepia-toned album cover featured the then 26-year-old wearing a corset wedding dress, accessorized with lace gloves and a hard-to-miss "Boy Toy" belt buckle.
"The photo was a statement of independence, if you wanna be a virgin, you are welcome. But if you wanna be a whore, it's your f—ing right to be so," Madonna reportedly said about the album's brow-raising imagery. Around this time, droves of "Madonna wannabes" copied her look, which incorporated jelly bracelets, rosaries, crucifixes, lace tights, and giant bow headbands — solidifying her as a fashion icon. (Earlier this year, Like a Virgin was added to the Library of Congress' National Recording Registry for being "culturally, historically or aesthetically significant.")
Madonna at the world premiere of her film, 'Who's That Girl' at the National Twin cinema in New York City on August 6, 1987.
Fresh off tying the knot with then-husband Sean Penn in 1986, Madonna's True Blue featured her first image makeover and veered away from the bubblegum-pop sound she was known for. Lead single "Live to Tell" displayed artistic growth as she seemingly confronts a painful past. ("I have a tale to tell/ Sometimes it gets so hard to hide it well," she sings in the ballad's opening verse.)
In addition, True Blue found Madonna experimenting with new musical styles, including classical ("Papa Don't Preach," which shined a light on teen pregnancy), Latin ("La Isla Bonita"), and doo-wop ("True Blue"). Still, dance-pop is at forefront of "Open Your Heart," as well as sexual innuendos in the accompanying video, which shows the singer performing as an exotic dancer at a peep show.
By the time 1989's Like a Prayer arrived, Madonna had earned the title of "First Lady of Pop," holding her own alongside male counterparts Michael Jackson and Prince. Leading up to the album's release, Madonna was battling a lot behind the scenes — she and Sean Penn filed for divorce two months prior, she reached the age her mother was when she died, and she was struggling with her Catholic upbringing.
In turn, the 11-track LP is considered the first of Madonna's projects to feature deeply personal lyrics and themes, particularly on tracks like "Till Death Do Us Part," "Promise to Try," "Oh Father," and "Keep It Together," the latter of which features Prince on guitar. On the flip side, "Cherish" and feminist anthem "Express Yourself" serve as bright spots on Like a Prayer.
The title track earned Madonna her seventh Hot 100 chart-topper, but it's most synonymous with its accompanying video. The clip depicts a number of controversial images, including Madonna singing in front of burning crosses, which cost the entertainer her Pepsi sponsorship contract (more on that later). "Like a Prayer" set the tone for Madonna's "Justify My Love" and "Erotica" videos, which caused their own controversies for their boundary-pushing imagery.
Madonna performs at the Blonde Ambition Tour at Feijenoord Stadion in Rotterdam, Netherlands on July 24, 1990 wearing a Jean Paul Gaultier conical bra corset.
The Sock Factor
It's impossible to revisit Madonna's catalog without reliving some of the performer's most jaw-dropping moments. From going on a profanity-filled rant on the Late Show with David Letterman in 1994 to kissing Britney Spears and Christinia Aguilera at the 2003 MTV Video Music Awards, Madonna is no stranger to shocking the world.
Only a year into her extraordinary career, Madonna stole the show at MTV's inaugural Video Music Awards. Donning a bridal gown reminiscent to the one she wore on the Like a Virgin album cover, the then 26-year-old unintentionally exposed her underwear while reaching for one of her heels that fell off as she made her way down from a 17-foot wedding cake. After the performance, Madonna was told by her manager that her career was over — but instead, it ended up catapulting her into superstardom.
To close out the '80s decade, Madonna was named Pepsi's spokesperson, but her $5 million sponsorship was revoked when the "Like a Prayer" video premiered a couple months later. The groundbreaking visuals depict racism against an interracial couple, stigmata, and Madonna herself kissing a Black saint — but its most provocative scene appears midway when Madonna sings in front of Ku Klux Klan-style burning crosses.
Madonna performs at The Girlie Show Tour at Sydney Cricket Ground in Australia on November 19, 1993.
Unsurprisingly, it was largely seen as blasphemous by the Christian community, with the pope calling for Italy to boycott the singer. Though the controversial video cost Madonna her Pepsi deal, it paved the way for artists to merge religion with their art to make a bold statement — seemingly inspiring the videos Lady Gaga's "Judas," Lil Nas X's "Montero (Call Me By Your Name)," and Sam Smith and Kim Petras' "Unholy." (In the same vein, part of Madonna's 2006's Confessions Tour was condemned due to performing "Live to Tell" on a mirrored cross while wearing a crown of thorns, simulating the crucifixion of Jesus Christ.)
Perhaps one of her most scandalous moments, though, belongs to the media frenzy and brilliance that was the "Justify My Love" video. Co-written with Lenny Kravitz, the song itself is raunchy enough to raise a few eyebrows, but still relatively tame by today's standards. "I want to run naked in a rainstorm/ Make love in a train cross-country," she coos over a Public Enemy-sampled drum beat.
Themes of nudity, sadomasochism, bisexuality, and androgyny run throughout the Jean-Baptiste Mondino-directed video, which Madonna defended as a "celebration of sex" after it was banned from MTV. Seizing the moment, Madonna released it as a video single, selling over a million copies at $9.98 — proof that Madonna could flip any potential career disaster into a shrewd business move.
Madonna: Truth or Dare premiered a mere six months later and received mostly positive reviews — though certain scenes sparked backlash, including Madonna performing fellatio on a glass bottle. The documentary chronicled the singer's 1990 Blond Ambition World Tour, but it's often hailed for championing the LGBTQIA+ community since it shows Madonna and her dancers attending a Pride parade and gay men casually discussing sex.
What followed next in Madonna's career was not for the faint-hearted: 1992's Erotica album examines every aspect of sexuality, from S&M and oral sex to the awareness of the AIDS epidemic.
Madonna's alter-ego named Dita takes center stage on lead single "Erotica," one of her most distinctive yet forgotten singles. "My name is Dita/ I'll be your mistress tonight," she declares over a slinky groove with hip-hop and Middle Eastern influences. The racy track and its follow-up single "Deeper and Deeper" claimed the No. 3 and No. 7 spots on the Hot 100, respectively, but the remaining Erotica-era singles didn't chart as high. "Bad Girl," which also appeared in the 1993 film Body of Evidence, peaked at No. 36 while "Fever" and "Bye Bye Baby" completely missed the Hot 100.
Gems like "Rain," "Words," "Waiting," and "In This Life" get buried in the controversy that surrounded the LP, but its impact still reigns three decades later, inspiring more female artists to flaunt their sexuality unapologetically; Beyoncé's "Partition," Christina Aguilera's "Not Myself Tonight," and Rihanna's "S&M" serve as a prime examples.
Madonna performs at the Re-Invention World Tour 2004 at The Great Western Forum in Inglewood, California on May 27, 2004.
The Blockbuster Hits
Madonna's acting chops weren't always well received by audiences, but her soundtrack hits came out swinging every time.
Originally recorded for 1985's Vision Quest film, "Crazy for You" marks Madonna's first time releasing a ballad as a single — flaunting her vocal abilities while appealing to more mature audiences. In addition to earning Madonna her second Hot 100 chart-topper, she picked up her first-ever GRAMMY nomination for Best Female Pop Vocal Performance.
A couple months later, "Into the Groove" appeared in the comedy Desperately Seeking Susan, which co-stars Madonna in the titular role and marks her film debut. Backed by synthesizers and drum machines, the song itself showcases Madonna at the height of her popularity, making it that much more special to listen to. Ironically, though, the infectious track never saw the Hot 100; it was ineligible to chart due to her label's decision to not officially release it as a single, out of fear it could overshadow "Crazy For You."
While Madonna's performance in the screwball comedy Who's That Girl was panned by critics, she scored No. 1 and No. 2 hits with "Who's That Girl" and "Causing a Commotion," respectively.
Madonna's acting aspirations continued throughout the decade. Despite starring in back-to-back box office disaster bombs, including Shanghai Surprise, she tried her hand at acting again in 1990 with Dick Tracy. Not only was the Oscar-winning film the box office comeback Madonna needed, but it birthed "Vogue," one of the most iconic dance tunes to ever grace airwaves — despite never appearing in the film.
Madonna performs at the G-A-Y in London on November 19, 2005 promoting her album 'Confessions On A Dance Floor'.
Topping the charts in over 30 countries, "Vogue" shined a light on a flamboyant style of dance stemming from Harlem's 1960s ballroom community led by Black and Latino gay men. From the spoken section (in which Madonna shouts out "Golden Age" Hollywood stars like Marlon Brando and Bette Davis) to the accompanying black-and-white video where Madonna debuts the now-legendary Jean Paul Gaultier cone bra, everything about "Vogue" is iconic and a cultural moment many artists can only dream of.
Madonna's film soundtrack success continued with 1992's A League of Their Own, 1996's Evita, and 1999's Austin Powers: The Spy Who Shagged Me. All three films' soundtracks demonstrate Madonna's constant willingness to push herself beyond her own artistic boundaries. On the operatic "Don't Cry for Me Argentina" and "You Must Love Me" from Evita, which earned her a Golden Globe and an Oscar nomination, Madonna explores musical theater as her voice reaches new heights. Meanwhile, the GRAMMY-winning "Beautiful Stranger" revisits 1960s psychedelic pop, hence the Austin Powers theme. Back by a live string arrangement, the melancholy "This Used to Be My Playground" off A League of Their Own is a testament to Madonna's many hats.
Though met with mixed reviews at the time of its early aughts release, "Die Another Day" is now considered quintessential Madonna and one of the highest charting James Bond songs in the U.S. At a whopping $6 million, its accompanying video remains the second most expensive, just behind Michael Jackson and Janet Jackson's 1995 "Scream" video.
Madonna performs at the UK leg of the international climate change awareness concert Live Earth at Wembley Stadium on July 7, 2007.
The Reinvention Periods
By late 1994, Madonna dialed down her sexed-up image following the release of back-to-back sexually explicit projects, including the controversial coffee table Sex book that featured softcore pornographic images of Madonna herself — along with Big Daddy Kane, Vanilla Ice, Naomi Campbell, and other famous faces.
For Bedtime Stories, she tapped R&B hitmakers like Babyface and Dallas Austin as she explored themes of love and romance versus the sexual freedom heard on 1992's Erotica. Radio-friendly singles "Take a Bow" and "Secret" marked a new musical direction for Madonna that paid off: both showcased some of her finest vocal performances and received glowing reviews from music critics.
But the entertainer's rebellious nature reappears on the criminally underrated "Human Nature" — an answer to the backlash she faced for her hyper-sexualized persona from two years earlier. "Did I say something wrong?/ Oops, I didn't know I couldn't talk about sex/ Did I stay too long?/ Oops, I didn't know I couldn't speak my mind," she sings on the song's bridge before declaring "I'm not sorry."
After enjoying the success of starring in Evita and becoming a first-time mother, 1998's Ray of Light marked Madonna's longest gap in between studio albums at the time — but the wait was well worth it.
Hailed as her magnum opus and her greatest reinvention, Ray of Light saw Madonna at her most creative due to motherhood and her spiritual awakening, as she experimented with techno-pop, electronica, trip hop, Middle Eastern sounds, and mysticism. With each song, the then 39-year-old transforms from Material Girl to Madonna the Artist, as evidenced on the title track, "Frozen," "Drowned World/Substitute for Love," "Nothing Really Matters," "Shanti/Ashtangi," and "The Power of Goodbye." She takes the theme of self-reflection a step further with songs like "Swim," "Mer Girl," and "Little Star," the latter of which is dedicated to her first-born child, Lourdes Leon.
Madonna performs at Sticky & Sweet Tour at Millennium Stadium in Cardiff, Wales on August 23, 2008.
Ray of Light boasts the biggest first-week sales by any female artist at the time of its release — an impressive feat given that the late '90s music scene was dominated by a sea of younger artists, including Backstreet Boys, Lauryn Hill, and Jay-Z. The 13-track LP earned Madonna three more GRAMMYs at the 1999 ceremony: Best Pop Album, as well as Best Dance Recording and Best Short Form Music Video for "Ray of Light."
With the arrival of 2000's Music, Madonna embarked on yet another transformation. In the new millennium, fans were introduced to Madonna the Cowgirl. While the title track sounded like a callback to her earlier dance hits like "Everybody," "Holiday" and "Into the Groove," follow-up single "Don't Tell Me" is notable as the pop icon's first time incorporating country stylings into her artistry.
The album's final single "What It Feels Like for a Girl," which calls out the double standards women face in society, only peaked at No. 23 on the Hot 100, but it remains a fan favorite and still holds its relevance today thanks to its feminist theme. Receiving four GRAMMY nominations across 2001 and 2002, Music's commercial success defied the music industry's limits on aging female entertainers — an issue Madonna is still confronting head-on today.
In 2003, following the 9/11 tragedy amid the Iraq war, Madonna felt moved to put out the politically driven American Life. It was a complete departure in both subject matter and sound, which leaned heavily toward "folktronica," a blend of folk and electronica music. "I'd like to express my extreme point of view/ I'm not a Christian and I'm not a Jew," she raps on the title track.
While Madonna's attempt to make a socially conscious record didn't produce the same payoff as other politically charged songs at the time (including Black Eyed Peas' "Where Is The Love?" and Green Day's "American Idiot"), the 11-track LP, if nothing else, displayed her willingness to take creative risks even two decades into her career.
Madonna performs at the MDNA Tour at the Lanxess Arena in Cologne, Germany on July 10, 2012.
The Dance Floor Classics
While Madonna got her start in New York City's club scene, her dance reign went into overdrive with the 1987 arrival of You Can Dance — which contains new track "Spotlight" plus a handful of remixed tracks off her first three studio albums. For You Can Dance, Madonna enlisted veteran DJs, including John "Jellybean" Benitez and Shep Pettibone. At a time when remixes were still uncharted territory, the club-ready LP remains the second best-selling remix album of all time and is considered the first album by a mainstream artist to be solely dedicated to the art of the remix.
While dance music lies at the core of Madonna's discography, her work shifted toward more of an adult-oriented sound after You Can Dance, beginning with 1989's Like a Prayer. After nearly two decades of musical experimentation, Madonna returned to her dance roots in a big way with 2005's Confessions on a Dance Floor.
The album's lead single "Hung Up" — built around a prominent sample of ABBA's "Gimme! Gimme! Gimme! (A Man After Midnight)" — smashed records when it skyrocketed to No. 1 in 41 countries. Its follow-up singles "Sorry," "Get Together," and "Jump" fared better internationally, but the LP's commercial success kicked off the 21st century's disco revival that later influenced the likes of Dua Lipa's Future Nostalgia and Lizzo's "About Damn Time."
Madonna performs at the MDNA Tour at The NIA Arena in Birmingham, England on July 19, 2012.
In 2007, Confessions on a Dance Floor won a GRAMMY for Best Electronic/Dance Album, and its accompanying Confessions Tour took home another GRAMMY for Best Long Form Music Video the following year.
With contributions from Justin Timberlake, Timbaland, Pharrell Williams, and Nate "Danja" Hills, 2008's Hard Candy is one of Madonna's lowest-selling albums, despite housing the massive hit "4 Minutes" (a collaboration with Timberlake), which reached No. 3 on the Hot 100. "4 Minutes" also earned Madonna her 37th top 10 single, making her the artist with the most top 10 entries at the time. Other standout tracks from Hard Candy include "Give It 2 Me," "She's Not Me," "Devil Wouldn't Recognize You," and "Miles Away," the latter of which was inspired by her then-husband Guy Ritchie.
Madonna performs at The 57th Annual GRAMMY Awards at the STAPLES Center in Los Angeles on February 8, 2015.
The Legacy Continues
Around the time when Madonna was crafting her 2011 directorial debut W.E., she was laying down the foundation for her twelfth studio album MDNA, which arrived the following year.
Out of the four singles released, "Give Me All Your Luvin'" (featuring Nicki Minaj and M.I.A.) is the only song to enter the Hot 100, though "Girl Gone Wild" and "Turn Up the Radio" became her 42nd and 43rd No. 1 dance hits. The guitar-led ballad "Masterpiece," which also appears on W.E.'s soundtrack, won for Best Original Song at the 2012 Golden Globes.
Despite not being released as a single, "Gang Bang" quickly emerged as a fan favorite while receiving criticism from those who said it glorified violence. Inspired by Quentin Tarantino's films, the aggressive song's lyrics depict a woman who murders an ex-lover: "And I'm going straight to hell/ And I got a lot of friends there/ And if I see that b— in hell/ I'm gonna shoot him in the head again/ 'Cause I want to see him die," she sneers on the bridge.
Madonna performs at the Rebel Heart Tour at Allphones Arena in Sydney, Australia on March 19, 2016.
Madonna's next two LPs, 2015's Rebel Heart and 2019's Madame X, didn't generate any massive hits, though Rebel Heart's "Living for Love" and "B— I'm Madonna" are the most recognizable. The latter's accompanying video features cameos from Beyoncé, Katy Perry, and Miley Cyrus, to name a few. Both albums, however, spawned an additional six No. 1 dance hits for Madonna. With a whopping 50 No. 1s on the Billboard Dance Club Songs chart, Madonna cemented her status as the dancing queen.
At the top of 2023, Madonna announced her upcoming Celebration Tour to commemorate her 40th anniversary since her debut. With 45 stops spanning from Detroit and Los Angeles to Amsterdam and Barcelona, the Celebration Tour was scheduled for a July 15 kickoff before getting postponed after the 64-year-old superstar's recent health scare.
As the tour name suggests, Madonna is ready to honor the hit-filled legacy she's built. "I am excited to explore as many songs as possible, in hopes to give my fans the show they have been waiting for," she said at the time of announcing the tour, which is her first dedicated to her greatest hits. When the megastar makes her glorious return to the stage later this year, she'll remind the world of her relentless spirit — the same one that made her a North Star for nearly every female entertainer on the charts today regardless of genre.
Madonna has supported gay rights, pushed sexual freedom, implemented religious imagery, and reshaped feminism at a time when it wasn't trendy to do so. All the while, she never has apologized for her "rebel heart" — solidifying her legacy as the true Queen of Pop.
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