ETI lists Madonna’s 20 Most Essential Magazine Covers

Madonna turns 60 on August 16, and she has amassed one of the greatest music catalogues in history — but her visuals have always been at least as important to her legacy.

At The New Music Seminar way back in 1984, Madonna clapped back at fellow panelist John Oates of Hall & Oates when he moaned that rockers shouldn’t have to act in videos, saying, “If someone puts a camera on you, what’s the difference?”

For Madonna, who never met a camera she didn’t lick, the difference has been between being regarded merely as a great artist and as one of the biggest icons of all time.

She even sings about fetishizing the striking of poses — and being “on the cover of a magazine.”

Check out these 20 career-defining Madonna magazine covers, from her virginal first to her lady-of-the-manor latest.

Dance Music Authority (1982)

The very first time Madonna’s face appeared on a magazine cover, the neophyte disco diva was shot by Peter Cunningham looking positively Pat Benatar-ish. The portrait was used on Dance Music Report for a piece about the brisk sales of her “Everybody” 12”. It was her first Warner Bros. shoot, and Cunningham had been prepped by Madonna’s publicist Liz Rosenberg to expect “the next Marilyn Monroe.” He laughed. He shouldn’t have.
Island (1983)

Island

Madonna’s first dedicated cover shoot was with downtown photographer Curtis Knapp for the arty NYC mag Island. Styled by her friend Maripol, she opted for a dramatic pose clearly inspired by Edward Steichen’s famous 1928 portrait of Greta Garbo — Madonna’s first homage! Inside, she said her oldest fantasies were to be Nancy Sinatra or a nun.
Rolling Stone (1984)

Rolling Stone

Rolling Stone writer Christopher Connelly compared Madonna to a siren in her first national U.S. cover story, framed her success with tales of the men she’d used to get where she was going, and asked, “Did she exploit people?” Luckily the cover line wasn’t sexist — oh, wait: “Madonna Goes All the Way.” The Steven Meisel cover was a nail-biter.
Time (1985)

Time

Hitting the big-Time, Madonna’s phenomenal success was dissected in detail in this monumental piece. Inside, Madonna, shot on a “Virgin Tour” stop by Francesco Scavullo, was already defensive when discussing her haters, noting, “If people don’t get the humor in me or my act, then they don’t want to.”
Playboy (1985)

Playboy

One of the few magazine covers that made Madonna cry is now, in retrospect, an indispensable part of her story. Hef bought pre-fame nudes of the fledgling superstar taken in 1979 by Lee Friedlander and Martin H.M. Schreiber, smacked a gorgeous Desperately Seeking Susanimage on the cover, and cashed in. Privately, Madonna panicked, but she bounced back and turned the scandal into an empowering moment. “I ain’t takin’ shit off today,” she stammered defiantly at “Live Aid” in reference to the scandal, and her, “So what?” response became an iconic New York Post cover that her pals Keith Haring and Andy Warhol turned into pop art.
Vanity Fair (1986)

Vanity Fair

Fast becoming her photographer of choice, Herb Ritts delivered a stunningly transformed Madonna for the cover of Vanity Fair in 1986. The magazine trumpeted her quick change from downtown diva to classic beauty.
Harper’s Bazaar (1988)

Harper’s Bazaar

Another incarnation — this time brunette! — was revealed by Scavullo for Harper’s Bazaar, the inside spread of which pictured the Broadway-bound babe (she helped Speed-the-Plowsell out its entire run) in haute couture, including an early donning of Gaultier.
British Vogue (1989)

Vogue

A totally unique Herb Ritts portrait of Young Blue Eyes made this issue of British Vogue a keeper. It heralded Madonna’s segue from bubblegum pop to the mature stylings of “Like a Prayer,” one of her masterpieces.
French Glamour (1990)

Glamour

Madonna’s “Blond Ambition” originated the tour template pop stars follow to this day — you can see and hear it every time you see Lady Gaga, Katy Perry, or Taylor Swift on the road. For the cover of this French Glamour issue, Jean-Paul Gaultier — who designed the tour’s costumes, including that cone bra — joined his muse, embracing her lovingly for Herb Ritts’s lens. It remains a stirring portrait of the collaboration, one that was continued as recently as this year’s Met Gala.
Interview (1990)

Interview

If you had to choose one quintessential Madonna cover, it could be this one. With her Judy Garland hair, Joan Crawford brows, Marilyn lips, and her most festive Blond Ambition duds, Madonna boldly grabs her crotch, making Elvis’s swivel hips and Michael Jackson’s crotch grab into a feminist manifesto. The only cover line needed? “Madonna!”
Vanity Fair (1991)

Vanity Fair

Teaming up with Steven Meisel, Madonna seemed to exorcise her obsession with Marilyn Monroe for the cover and layout of this issue of Vanity Fair, recreating several of her idol’s famous poses. The cover promoted Truth or Dare—which became the no.1-grossing doc of all time up till then — and she looked so flawless on it she wore the same look to that year’s Oscars … with Michael Jackson as her date. Madonna invented “extra.”
The Advocate (1991)

The Advocate

Though Madonna had already praised her gay mentor — dance teacher Christopher Flynn — back in 1984 in Rolling Stone, and had been an outspoken advocate of gay rights, her no-holds-barred interview with The Advocate in 1991 made her an honorary gay man. Among many other things in the wide-ranging piece, Madonna said, “Straight men need to be emasculated. I’m sorry. They all need to be slapped around. Women have been kept down for too long. Every straight guy should have a man’s tongue in his mouth at least once.” She was an early opponent of toxic masculinity! On the cover, Madonna encounters an implied penis with all the seriousness of Charles Pierce.
Entertainment Weekly (1992)

EW

Entertainment Weekly got plenty of mileage out of a Steven Meisel image from Madonna’s controversial Sex book showing the singer hitchhiking in the nude. More people picked up that cover than any other EW cover that year.
Esquire (1994)

Esquire

Trying to recover from an all-out assault by the media over her Sex book and an off-putting interview with David Letterman, Madonna returned on a 1994 Esquire cover shot by Wayne Maser that pictured her on a target. She didn’t back off presenting herself as a sexual being, this time in a rubber bikini with a dog chain around her throat. The Q&A with irascible Norman Mailer inside was mind-blowing, including Mailer proclaiming her our “greatest living female artist.”
Vanity Fair (1996)

Vanity Fair

Twenty years later, Italian-American Madonna might not have gotten away with playing the lead role in the film version of Evita. Back in 1996, she had everyone but Patti LuPone rooting for her when she assumed the role, and a stunning cover by Mario Testino seemed to seal the deal that she’d been born to play the part. Inside, she offered her on-set diaries from the making of the movie that probably came close to nabbing her an Oscar nomination and that delivered to her a Golden Globe.
Spin (1998)

Spin

Spin publisher Bob Guccione Jr. had previously detested Madonna, but they kissed and made up a couple of years before this arresting Inez van Lamsweerde and Vinoodh Matadin cover hailed her creative comeback with Ray of Light as “her most daring album in years.”
W (2003)

W

Madonna moved on from her old favorites with Steven Klein, posing for a 44-page W portfolio that also became an art installation and a book so rare it now sells for thousands. For “Madonna Unbound,” the 44-year-old reasserted her avant-garde roots as she launched her least commercial album, American Life.
Elle (2006)

Elle

Gilles Bensimon captured Madonna’s ‘70s-flashback look for Elle in 2006, an accessible reinvention just in time for the release of her popular Confessions on a Dance Floor album.
Interview (2010)

Interview

Critics were not thrilled with her Hard Candy album, but Madonna reminded everyone she knew exactly who she was with this stunning shoot by Mert Alas & Marcus Piggott, a return to form that found the 51-year-old star embracing looks more than slightly reminiscent of her ‘80s BOY TOY phase.
Vogue Italia (2018)

Vogue

Mert & Marcus did the honors again when Madonna decided to do a cover (two, in fact) celebrating her 60th birthday. Though the Vogue Italia team had envisioned a career-retrospective shoot, the resolutely non-nostalgic Madonna instead firmly requested a cover and spread reflective of her newfound family bliss in Portugal. She moved there, she says inside, partly because, “This is not America’s finest hour.”