SPECIAL EDITION

The Queen of Pop!

SPECIAL EDITION

GIVING
GOOD FACE
A moment from
the Truth or
Dare film, 1991.
 PRIMA DONNA
In Venice for the 2011
premiere of W.E., which
Madonna directed. The
film earned a Golden
Globe for her original
song “Masterpiece.”
 50
YOU MUST
LOVE ME
In the ’90s Madonna
vogued, revamped the
celebrity documentary and
earned acting honors
MADONNA
68
4 ICONIC
STAGES OF DON’T-MISS
HER LIFE MOMENTS
A four-decade gallery The concert stage
of the evolving alone can’t contain her.
spectacle of Broadway, late-night
Madonna’s tours TV and other
places Madonna
20 made her mark
AMERICAN LIFE
The star in her 72
early years, from LIVE TO TELL
suburban Detroit to The new millennium
New York City’s saw a growing family,
East Village. broader interests
and a deep devotion to
26 dance music
GET INTO
THE GROOVE 84
Planting a flag as an MTV TAKE A BOW
pioneer and the Rest on her laurels?
ultimate ’80s star No, thanks. The Madonna
of today is hitting
46 the road again, giving fans
CAUSING A something to celebrate
COMMOTION
From the start, controversy
was part of the act.
Are you shocked?
 SUITED UP
Madonna’s 1990 Blond Ambition tour (above, in Paris) was the first
time many saw Jean Paul Gaultier’s coned corsets. But the designer had
shown them on runways since the early ’80s.

4
FOUR DECADES OF TOURS

M A D O N N A’ S C O N C E R T S H AV E A LW AY S
SERVED SONGS, SEX, STRENGTH
A N D E N D L E S S S P E C TA C L E . N O O N E P U T S O N
A S H O W T H E W AY S H E D O E S

MADONNA PEOPLE 5
 MADONNA ON STAGE

‘THAT WHOLE TOUR WAS CR A ZY,

BECAUSE I WENT FROM PL AYING
CBGB AND THE MUDD CLUB
TO PL AYING SPORTS ARENAS’
—MADONNA , TO ROLLING STONE

THE VIRGIN TOUR, 1985

Early shows were played before crowds of
just 3,000-5,000. “I want fans to be able to
see Madonna sweat,” manager Freddy
DeMann told People. Above: in Detroit.

6 MADONNA PEOPLE
Just try to understand
I’ve given all I can
’Cause you got the best of me

Forty years ago this summer,

Madonna gave us Madonna,
her joyous, synthy, funky,
twinkly first album, which
announced a new rising star
even as it grounded feet on
dance floors. If it didn’t signal
that this star would someday
grow into an icon, it did
deliver on the promise of
those “Borderline” lyrics:
Madonna has long given us
her best. It’s made her the
top-selling female recording
artist ever. And perhaps
surprisingly for an artist so
associated with music videos
and club remixes, Madonna
became, after 11 world tours,
the highest-grossing female
live performer. But while
others of her generation (and
some younger) turned to
highbrow Broadway career
retrospectives, lowbrow
jukebox musicals or other
nostalgia fests, Madonna
continued to tour the same
way in her 60s as she had in
her 20s: in support of new
music. Every couple of years
she tried on fresh looks,
played in unexplored genres,
and gifted fans with new
collections of songs. “I’m not
a ‘greatest hits’ kind of girl,”
said Madonna in 2015 as she
set out on the Rebel Heart
tour. “I mean, Picasso didn’t
paint the same paintings over
and over again.” In 2023 she
dropped two new singles:
“Vulgar” with Sam Smith and
“Popular” with the Weeknd
and Playboi Carti; the tracks
made her one of very few
artists to chart in five
decades. On the 40th
anniversary of her debut,
People looks back at
Madonna’s singular career:
onstage and off, hits and
misses, shocks that now seem
tame and her open invitation
to all to dance and sing, get
up and do your thing.

7
 MADONNA ON TOUR

WHO’S THAT GIRL, 1987

Madonna (above, in
Chicago) wore a bustier
Marlene Stewart had
designed for the “Open Your
Heart” video. It was later
acquired by—and stolen
from—Frederick’s of
Hollywood Lingerie Museum.

8 MADONNA PEOPLE
 BLOND AMBITION, 1990
Truth or Dare spotlighted those sharing the stage on Madonna’s third tour. Above: dancers Luis Camacho and Jose Gutierez (who together choreographed
the “Vogue” video) as mermen. Below: Camacho in “Like a Virgin”; singers Donna De Lory and Niki Haris in a Fosse-esque “Keep It Together.”

9
 THE GIRLIE SHOW, 1993
Madonna launched her tour
in London to promote her
album Erotica. Reviews were
mixed: While Newsday called
it “part big-top circus, part
Broadway musical and part
soft-core porn act,” The New
York Times saw it as “a
good-time song-and-dance
revue, not a provocation.”

DROWNED WORLD, 2001

Some 18,000 fans in
Barcelona happily sang along
with the superstar as she
dressed up as a cowgirl and
performed “Don’t Tell Me.”
Returning were singers Niki
Haris and Donna De Lory.

10
 MADONNA ON TOUR

RE-INVENTION, 2004
Along with designers Stella McCartney,
Christian Lacroix and Karl Lagerfeld,
Tony-nominated costumer Arianne Phillips
dressed Madonna (here, in L.A.) on what was
that year’s highest-grossing tour.

MADONNA PEOPLE 11
 ‘THERE ISN’T A SECOND IN MY
DAY THAT ISN’T TAKEN UP
LOOKING AFTER MY FAMILY OR
THINKING ABOUT MY SHOW ’
—MADONNA , 2001

12 MADONNA PEOPLE
 MADONNA ON TOUR

CONFESSIONS, 2006
During “Future Lovers” (here, in Germany) the singer emerged from
a mirror ball, a reminder that—for all the elements of sex, religion and other
hot-button issues—a Madonna concert is primarily about dancing.

13
 STICKY & SWEET,
2008-09
At 50, Madonna (here,
in London) “seems even
more determined to
prove that she doesn’t
stand still,” noted the
BBC. “And she certainly
doesn’t slow down.”

14
MADONNA ON TOUR

MADONNA PEOPLE 15
 MADONNA ON TOUR

‘IT’S HARD TO
WATCH MYSELF
DO ANYTHING.
I CAN’T EVEN
STAND TO
WATCH MYSELF
IN CONCERT’

MDNA, 2012
During the tour Madonna (here, in Ramat Gan,
Israel) raised such issues as gun violence and
human rights violations, releasing a letter to
Billboard noting that “We cannot allow our anger
or bitterness to swallow us up.”

16 MADONNA PEOPLE
REBEL HEART, 2015-16
When Madonna sang the French
classic “La Vie en Rose” in Montreal
(above)—and apologized about
her nonfluent French—the Associated
Press reported that the audience
“went wild and sang along.” In Brooklyn
(right) she strummed a ukulele.
 MADONNA ON TOUR

MADAME X, 2019-20
The star reimagined her show
for an intimate theater stage, with
The New York Times writing that at
61, “Madonna is still taking
chances.” The tour was cut short in
early 2020 because of COVID,
and a documentary chronicling it
appeared in 2021 (above).

18
‘MADAME X IS A SECRET AGENT
TR AVELING AROUND THE
WORLD, CHANGING IDENTITIES,
FIGHTING FOR FREEDOM . . .’
—MADONNA

MADONNA PEOPLE 19
 HER
EARLY
YEARS

AMERICAN
LIFE
A DA N C E R I N D E T R O I T, A N E A S T V I L L AG E P U N K E R A N D
C L U B K I D I N N E W Y O R K , M A D O N N A B E AT A S U R P R I S I N G P AT H
TO G E T T I N G H E R F I R S T B R E A K
By JED GOTTLIEB

even as a seventh grader in suburban detroit, Madonna entertained, edu- MADONNA AS CHILD
cated and shocked—in a mild, junior high school way. For West Middle School’s Above: Madonna
Louise Ciccone, age
talent show, the 12-year-old, covered in Day-Glo colors, danced to the Who’s 10 in 1968, a few
“Baba O’Riley”—a rebellious rock anthem powered by the climatic cry of “It’s only years before she made
teenage wasteland.” She considered it her first provocative performance. her stage debut at a
Born Aug. 16, 1958, Madonna Louise Ciccone grew up in a large Ital- West Middle School
talent show in
ian American family touched by tragedy. At just 5, she lost her 30-year-old suburban Detroit.
mother and namesake, Madonna Louise Fortin, to cancer. As an adult Ma- Right: Newly arrived
donna explored the pain through music, most notably in “Promise to Try” in New York City,
from 1989’s Like a Prayer. But as a kid in a crowded family—she was one of 10 years later.
eight siblings raised by father Silvio Ciccone and stepmother Joan—Madonna
found release in dance.
Childhood friends have described Madonna as sensitive, shy and smart,
arty, flirtatious and troubled, depending on whom was asked—everybody re-
membered the star-in-the-making differently. But they seem to agree on one
thing: Madonna shone on the dance floor. Preteen jazz and tap lessons led to
cheerleading in high school, cheerleading to serious ballet studies, ballet to an

20 MADONNA PEOPLE
 HAPPY TO BE BACK
As a Rochester
Adams High School
sophomore in Rochester
Hills, Mich., Madonna
(far right) flashed a smile
during a homecoming
event in 1974.

SHE’S GOT SPIRIT

Madonna had the
ambition but lacked the
blonde locks when she
performed with
the junior varsity
cheerleading squad
at Rochester Adams
High in 1974.

WHO’S THAT GIRL ?

Far right: Even as a
teenager in small-town
Michigan, Madonna had
a sense of style that set
her apart from her peers.

escape from her traditional religious upbringing.
“Ours was a strict, old-fashioned family,” Ma-
donna told People back in 1985. “When I was tiny,
my grandmother used to beg me not to go with men,
to love Jesus and be a good girl. I grew up with two
images of a woman: the virgin and the whore. It was
a little scary.”
Mentor and ballet teacher Christopher Flynn
gave Madonna a glimpse beyond the borders of her
midwestern suburb, introducing her to art, classical
music and gay dance clubs in Detroit pulsing with
the beats of the flourishing disco culture. Flynn, who
died in 1990, spoke of her to People as “a very worldly
sort of woman even as a child. We would go to gay
bars, and she and I would go out and dance our asses
off. People would clear away and let her go.”
In 1976 the 17-year-old—a straight-A student—
graduated Adams High a semester early and headed
to the University of Michigan in Ann Arbor on a dance
scholarship. A year later she won another scholarship,
this time to the Alvin Ailey American Dance Theater’s
New York City summer workshop. New York hooked
her. With a loving push from Flynn, she dropped out
of college and stormed the city.
Her dance skills opened doors—musical-theater
auditions got her singing; her strong sense of
rhythm made her a natural drummer. Madonna’s
curiosity, ambition and determination did the rest.
Between day jobs, including stints at fast-food
joints and the famed Russian Tea Room, she con-
nected with every corner of the city’s wild arts
scene. She performed with professional modern

22

dance companies. She acted in a low-budget art film.
She sang and played drums and guitar in a series of
rock bands, including Emmy (“Burning Up”). She
dated painter Jean-Michel Basquiat and befriended
artists Andy Warhol and Keith Haring.
In the ’80s Madonna started to write her own
songs. With on-again, off-again boyfriend Ste-
phen Bray, she produced a four-song demo of her
originals. Then she slipped future boyfriend Mark
Kamins one of those tracks while he was deejaying at
legendary club Danceteria. Kamins spun it, and the
crowd liked what it heard: “Everybody” was a sim-
ple, hypnotic throb that bridged disco and new wave.
“She had this incredible sense of style,” Kamins
told Time magazine in 1985. “She had an aura.”
Kamins connected Madonna to Sire Records
EARLY YEARS
founder Seymour Stein, the music executive who
had signed the Ramones, the Pretenders and Talk-
ing Heads. Stein played the complete demo. Then
he played it again. Then he invited Madonna to
his hospital room, where he was recovering from
a heart infection. (Stein, who remained close with
Madonna throughout her career, died in April.)
“When she walked into the room, she filled it
with her exuberance and determination,” Stein told
People. “It hit me right away. I could tell she had the
drive to match her talent.”
Madonna had spent half a decade grinding it out
in punk dives, dance troupes and Dunkin’ Donuts.
She wasn’t going to wait any longer.
The debut single for Sire Records was a polished up
version of “Everybody” produced by Kamins. The DJ
MADONNA PEOPLE 23
 STRIKE A POSE:
By the spring of 1979,
Madonna had become
a New York club kid who
spent as much time
dancing in discos as she
did onstage.

24
 EARLY YEARS

‘I HAVE ALWAYS BEEN

RESOURCEFUL , WHETHER IT
WAS CONVINCING MY
FATHER TO LET ME STAY
OUT L ATE OR GETTING OUT
OF PAYING A CAB FARE IN
NEW YORK WHEN I DIDN’T
HAVE ANY MONEY’
—MADONNA , 1985

didn’t really know how to produce. Madonna,

who had no training as a singer and had never
been in a professional studio, belted out the
jam in one take. And yet, the two amateurs
delivered a dance anthem.
Released Oct. 6, 1982, “Everybody” missed
the Billboard Hot 100 singles chart. But it
INVENTION AND
REINVENTION: hit No. 3 on the U.S. Dance Club Songs chart.
Madonna’s style Enough to serve as a proof of concept. Sire
evolutions started long wanted an album.
before she hit the charts.
In early 1979 she
straddled punk and
new wave.

BURNING UP:
Having cycled through a
series of underground
rock bands and modern
dance troupes,
Madonna took center
stage as an upcoming
pop star in 1983.

25
 THE ’80S

D I D M A D O N N A M A K E M T V, O R D I D M U S I C
V I D E O S M A K E H E R ? D E B AT E A W AY !
W H AT ’ S I N A R G U A B L E : S H E D O M I N AT E D
T H E D E C A D E L I K E N O OT H E R
By JED GOTTLIEB

madonna invented the ’80s.

An arguable assertion? Perhaps. But Madonna, more than any other artist
of the MTV era, perfected its defining unification of sound, vision, hype, pop
and personality.
After disco was declared dead, Madonna’s 1983 self-titled debut album
made the world dance again. Blending ’70s club music with synth pop and
R&B, the album spun off hit after hit—“Borderline,” “Holiday,” “Lucky Star”—
and went on to sell 10 million copies worldwide. A blockbuster, Madonna
barely teased what was to come.
At MTV’s first Music Video Awards on Sept. 14, 1984, Madonna insisted
on performing a then-unreleased song, “Like a Virgin.” And she wanted to
perform it wearing a white wedding gown and veil, a bustier, garters and a
“BOY TOY” belt buckle. The only thing people remember about the show is
Madonna. (Try to name another moment from that night.)
A few weeks later the “Like a Virgin” video doubled down on the
provocativeness. Shot on the canals of Venice for an outlandish estimate

26 MADONNA PEOPLE
 DRESS YOU UP
In 1984 Madonna went
global. Here she takes
over London, or at least
a corner of it, during a
photo shoot at the city’s
Holborn Studios.

27
 BRACE YOURSELF
Before Madonna’s
Like a Virgin album appeared
in 1984, she posed in
Amsterdam. A French stylist,
Maripol, had introduced her
to what became her
signature rubber bracelets.

28

VIDEO STAR
Madonna and then boyfriend DJ John “Jellybean” Benitez at the opening
of New York nightclub Private Eyes on July 17, 1984.
of $150,000 (about $438,000 in 2023), the video
featured Madonna purring and dancing on gondo-
las while a circus lion roamed the set (as an armed
trainer stood close by “just in case”). “Like a Virgin”
became her first No. 1 single, spending six weeks at
the top spot.
Madonna whiplashed her look from disco-punk
bohemian to silver screen glamor for “Material
Girl.” Another big-budget affair, the video paid hom-
age to the 1953 Marilyn Monroe musical Gentlemen
Prefer Blondes while poking fun at wealth-obsessed
yuppies. The No. 2 hit celebrated Madonna’s sub-
versive nature.
Both the lyrics to and videos for “Material Girl”
and “Like a Virgin” showed off how Madonna ex-
THE Õ80S
celled at pairing satire with Top 40 glory. Any critic
who labeled her as vapid, disposable or materialistic
missed how sly and subversive she could be—even
at the start of her career. “Whether it was ‘Material
Girl’ or ‘Like a Virgin’ or whatever, you can’t take
anything I say literally,” Madonna reflected in a
2022 Paper magazine interview. “Everything I say is
said with irony or tongue-in-cheek or there are mul-
tiple meanings. . . . The confusion and the mystery
and the wink and the smile were all very important
elements, not only in the music and the record but
in terms of establishing me and what I stand for as
an artist.”
Madonna crafted 1984’s Like a Virgin with super
producer (and Chic alum) Nile Rodgers, who had
MADONNA PEOPLE 29
 CELEBRATE
Hours after wrapping up the final concert on 1985’s Virgin tour at Madison Square Garden,
Madonna and band let loose at an afterparty at the New York City club Palladium (above).
Madonna channeled Marilyn Monroe while filming the video for “Material Girl” in 1985 (right).

previously brought forth David Bowie’s Let’s
Dance. The album’s hooks, charm and cheeki-
ness pushed it to sell more than 21 million
records worldwide.
By 1985 Madonna was everywhere: at the
movies, playing a free spirit in director Susan
Seidelman’s hit film Desperately Seeking Susan;
headlining her first tour; and that July 1985
onstage at the Live Aid concert before an audi-
ence of 89,484 people at Philadelphia’s John F.
Kennedy stadium, in a show broadcast to 1.9
billion in 150 countries. For that performance
she wore an uncharacteristically modest stage
outfit of a flowered pantsuit and high-collared
blouse—perhaps a reaction to having early pre-
fame nude art-modeling photos published with-
out her consent in both Playboy and Penthouse
earlier that year. “I’m ain’t taking s--- off today,”
she quipped.
In August she found time to marry actor Sean
Penn at a friend’s home in Malibu with a starry
guest list that included Tom Cruise, Cher and
Andy Warhol. In love, she next delivered an al-
bum, True Blue, with the unabashed declaration
“Open Your Heart.” But she was still Madonna
and morphed again. She ditched the diamonds,
lingerie and rosary beads of the Virgin era and
debuted a bleach-blonde pixie cut for the “Papa
Don’t Preach” video, in which she played an
(Continued on page 34)

30 MADONNA PEOPLE
 THE ’80s

‘BRUCE
SPRINGSTEEN
WAS BORN
TO RUN.
I WAS BORN
TO FLIRT’
—MADONNA ,
TO PEOPLE, 1985

31
 THE ’80s

32 MADONNA PEOPLE
 CRAZY FOR HER
A Madonna-wannabe
contest at a London
nightclub in 1985.

33
 ONSTAGE AT LIVE AID
Madonna performed on a bill that included Duran Duran,
Led Zeppelin and Tina Turner at the Philadelphia edition of
the landmark July 13, 1985, charity concert.

(Continued from page 30)

unwed pregnant woman butting heads with
her father (Danny Aiello). Noting in a 1986
New York Times interview that it was a work
“that everyone is going to take the wrong
way,” Madonna managed to anger members of
Planned Parenthood, which suggested it glori-
fied teenage pregnancy, and to delight conserva-
tives, who interpreted the song as an antiabor-
tion anthem.
All fine by her. As Madonna told the Times,
“I like challenge and controversy—I like to tick
people off.” Controversy was the currency that
had, in part, fueled her ascent. So it came as a
shock to suffer her first failure, the 1986 box
office bomb Shanghai Surprise, costarring her
husband, Sean Penn. Critics also panned her
(Continued on page 39)

34 MADONNA PEOPLE
 THE ’80s

CLASS OF ’85
Backstage at JFK Stadium during
Live Aid, Madonna posed with
(back row, left to right) Keith Richards,
Daryl Hall, John Oates, Ron Wood,
(front row, left to right) Tina Turner,
Mick Jagger and Bob Dylan.

35
 THE ’80S

‘EVEN WHEN I WAS

A LITTLE GIRL , I KNEW
I WANTED THE WHOLE
WORLD TO KNOW
WHO I WAS, TO LOVE
ME AND BE
AFFECTED BY ME’
—MADONNA , 1985

36 MADONNA PEOPLE
 WATCH OUT!
Madonna came home on Aug. 7, 1987,
to headline the Pontiac Silverdome in
Pontiac, Mich., where she performed
“Open Your Heart” with 13-year-old dancer
Chris Finch. The date was part of the
Who’s That Girl tour promoting her True
Blue LP and Who’s That Girl soundtrack.

37
 EXPRESS
YOURSELF
In 1989 Madonna
spent millions and
oversaw every detail
to create one of her
most iconic videos.
The work resulted in
three MTV Video
Music Awards wins.

38

LIKE A PRAYER
The album, the song and the video were all inescapable in 1989, pushing the star’s fame—
and infamy—to unprecedented levels.
(Continued from page 34)
1987 screwball comedy throwback Who’s That Girl
(which has since earned a cult following). But she
boomed with every music release. Over 18 months
in ’86 and ’87, she tallied seven Top 5 singles, three
smash albums (True Blue, the remix LP You Can
Dance and the Who’s That Girl soundtrack) and a
series of must-see videos that embraced androgyny
and gay culture while evoking art-house cinema and
Hollywood archetypes.
But every controversy and career triumph was
purely a prologue to the title track of her 1989
album Like a Prayer. In January 1989 Madonna
THE Õ80S
signed a $5 million deal with Pepsi. On March 2 she
teased the new single in a feel-good two-minute TV
commercial for Pepsi. The next day MTV debuted
something very different. The full video for “Like
a Prayer” included stigmata, a stabbing, an inter-
racial love story and Madonna dancing in front of
burning crosses.
Pepsi canceled the ad and its sponsorship of
Madonna’s upcoming tour. Pope John Paul II con-
demned the video. But “Like a Prayer” became
a phenomenon. The single spent three weeks at
No. 1. The video won MTV’s 1989 Viewer’s Choice
Award, a category sponsored by Pepsi.
MADONNA PEOPLE 39
 THE ’80s

BECAUSE IT WAS THE ’80s

With David Lee Roth,
celebrating the Van Halen frontman’s
birthday on Oct. 10, 1984.
(Not, for the record, as a couple.)

40 MADONNA PEOPLE
 FRIENDS AND A LOVER
Madonna was joined by artist Keith Haring and comedian Sandra Bernhard at a benefit to raise money for rain forest conservation in 1989
(above). The star and then husband Sean Penn at an AIDS benefit in Los Angeles in 1987 (below).

She made headlines again when the price tag

for her next project, the “Express Yourself”
video, ran into the millions, making it one of the
most expensive ever produced.
Directed by David Fincher—who went on to
make Fight Club and other acclaimed films—and
meticulously overseen by Madonna, the video
used Fritz Lang’s 1927 science-fiction epic Me-
tropolis as inspiration to create an intensely erotic,
unfailingly beautiful work of art. Equally impor-
tant: It featured Madonna reclaiming the crotch
grab as a symbol of women’s empowerment.
Like a Prayer proved Madonna was a dynamic
artist: mature and playful, earnest and satirical,
poppy and experimental. It dealt with religion
and death, her childhood and her 1989 divorce
from Sean Penn. The album ensured that Ma-
donna exited the decade as the world’s definitive
pop star and provocateur. But she wanted to be
all that and a Hollywood icon.
42 MADONNA PEOPLE
 THE ’80s

IN HER ELEMENT
Madonna meets the press at the
12th Annual American Music Awards
on Jan. 28, 1985, at the Shrine
Auditorium in Los Angeles.

43
44 MADONNA PEOPLE
AT THE
MOVIES
BEING MORE
THAN A MUSIC
STAR WAS ALWAYS
THE PLAN
As soon as her videos
got her noticed, Madonna
leaped to the big screen
in (clockwise from
opposite) Desperately
Seeking Susan (1985
with Rosanna Arquette),
Bloodhounds of Broadway
(1989 with Jennifer
Grey), Who’s That
Girl (1987 with Griffin
Dunne), Shanghai
Surprise (1986, below with
producer George Harrison
and costar Sean Penn)
and Vision Quest (1985),
in which she played a
singer who delivered the
hit “Crazy for You.”
 1. PEPSI BOWS OUT AFTER
“LIKE A PRAYER” BACKLASH, 1989
A saint statue brought sexily to life, an
interracial kiss, burning crosses—Madonna
and director Mary Lambert knew the pots
they were stirring with the “Like a Prayer”
video. Still, they had, Lambert told Rolling
Stone, “underestimated the influence and
bigotry of fundamentalist religion.”
When Pepsi used the song for an ad with
different imagery—Madonna recalling
her childhood—religious-right groups
boycotted. The soda company
pulled the spot, while Madonna doubled
down, telling The New York Times: “Art
should be controversial.”
Perhaps. But not commerce.

10 CONTROVERSIES

CAUSING A
COMMOTION
N O T H I N G ’ S R E A L LY S H O C K I N G N O W , B U T A T T H E T I M E ,
M A D O N N A M A D E P R O V O C AT I O N PA R T O F T H E A C T

46
 2 3

4
2. “LIKE A VIRGIN” AT THE FIRST VMAS, 1984
Madonna wanted a white Bengal tiger beside her.
MTV balked at the jungle cat, but the young star
delivered something more ferocious. After
descending from a 17-ft.-tall cake in white lingerie,
Madonna writhed against the stage. Her manager
was told that her “career was over with.” Instead,
MTV would eventually call it “one of the most iconic
pop performances of all time.”

3. MADONNA PLAYS A PREGNANT TEEN, 1986

Though she was 27 when she filmed “Papa Don’t
Preach,” Madonna (a pro-choice proponent) played
a girl still living at home with her dad (Danny Aiello)
when she gets “in trouble deep” and makes up her
mind to keep the baby, potentially making teen
motherhood as attractive as her black bustier. “She
has more impact on young teenagers than any other
single entertainer since the Beatles,” said the head of
New York City Planned Parenthood. “That’s what
makes this particular song so destructive.”

4. MTV BANS “JUSTIFY MY LOVE”, 1990

How to go viral before the Internet: Make a steamy
video that, despite arty black-and-white footage
directed by Jean-Baptiste Mondino, doesn’t disguise
its hints of S&M and bisexuality or its flash of nudity.
Second, get MTV—the network that played Mötley
Crüe’s stripper-heavy “Girls, Girls, Girls” roughly a
billion times—to refuse to air it. Third, sell the clip on
videotape at $10 a pop, letting the inevitable news
coverage do the work of promoting it. Voilà!

MADONNA PEOPLE 47
 ARE YOU SHOCKED?
5

5. BLOND AMBITION’S
SIMULATED SOLO SEX, 1990
Pope John Paul II urged a
boycott. Canadian police stood
by to arrest her. Her own dad
said he could have done without
some bits. People still talk about
the tour’s “Like a Virgin,” which
included mimed masturbation.
Less discussed: how Madonna—
once she had everyone’s
attention—used her stage to
advocate for safe sex.

6. SEX, THE BOOK, 1992

Yes, Sex was a book. It was a
book full of nude pictures of
Madonna, whips and chains,
same-sex eroticism and risqué
snapshots of celebs from Isabella
Rossellini to Vanilla Ice. But it
was really a pop culture event.
Fans spent $75 million to buy
every copy of the one-time print
run of 1.5 million.
6

7. MADONNA TO DAVID
LETTERMAN: “#@$!”, 1994
“You realize this is being
broadcast, don’t you?” asked the
exasperated host. Oh, she did.
Foulmouthed and funny,
Madonna began by giving her
panties to Letterman. It got
worse, or better, from there.
For some it was a career low—
but one with high ratings.

8. KISSING THE GIRLS, 2003

A champion of same-sex love
and of tempests in teapots,
Madonna smooched (yawn)
both Britney Spears and Christina
Aguilera at the MTV Awards.
A camera fixed on Spears’s ex
Justin Timberlake caught the
only big reaction to the stunt.

48 MADONNA PEOPLE
 8

10

9. TV DEEMS A GUY RITCHIE-

DIRECTED CLIP TOO VIOLENT, 2001
Madonna and then husband Ritchie’s
collaboration on “What It Feels Like for a
Girl,” in which she played a woman on a
violent, vengeful spree, was too much for
MTV and VH1. Each aired the video only
once before pulling it.

10. ON THE CROSS, 2006

On her Confessions Tour, Madonna, in a
crown of thorns, placed herself on a mirrored
cross. Religious groups boycotted. NBC cut
the image from a concert special. “It is no
different than a person wearing a cross or
‘taking up the cross,’ as it says in the Bible,”
said Madonna. “My performance is neither
anti-Christian, sacrilegious or blasphemous.
Rather, it is my plea to the audience to
encourage mankind to help one another.”

49
 THE ’90s

I N A B R E AT H L E S S D E C A D E , M A D O N N A I N V I T E S
A L L TO V O G U E , R E VA M P S C E L E B R I T Y D O C S ,
W I N S A N AC T I N G AWA R D , M A K E S T H R E E S T U D I O
A L B U M S—A N D R EI N V EN TS H ER SEL F A S A M O M
By JED GOTTLIEB

“i know that i’m not the best singer, and I know I’m not the best dancer, but
I’m not interested in that,” Madonna admitted in the 1991 documentary Truth or
Dare. “I’m interested in pushing people’s buttons, in being provocative and in be-
ing political.” Point well taken. During the ’90s she sang, she toured, she danced,
she acted, but, memorably, she pushed a ton of buttons while finally finding the
perfect film part for herself: Madonna.
Truth or Dare was a landmark event. This was before The Osbournes made
celeb reality TV a genre, eons before now-common pop star docs like Beyoncé’s
Homecoming or Taylor Swift’s Miss Americana. Then the highest-grossing docu-
mentary of all time, the film, directed by 26-year-old newcomer Alek Keshishian
and executive-produced by Madonna, took audiences behind the scenes of her
Blond Ambition tour for a racy, raw look at the art and chaos swirling around her.
It combined everything Madonna excelled at—giving live performances choreo-
graphed for maximum controversy, delivering diva attitude offstage—even as
it deepened her mystique. Here was Madonna at her mother’s grave. And here,
explaining to her father that “I can get you tickets any night” of her tour. It also

50
 IN A NEW LIGHT
After making movies—and a
baby—Madonna capped the
decade with the acclaimed
1998 album Ray of Light
and, in the video for the title
track, a new Earth-mother
disco-queen persona.

MADONNA PEOPLE 51
 THE ’90s

‘MADONNA SAID
TO ME THAT
PEOPLE TALK
ABOUT HOW
FAME CHANGES
YOU BUT NEVER
ABOUT HOW IT
CHANGES PEOPLE
AROUND YOU’
—ROSIE O’DONNELL

52
 HOLLYWOOD
PLAYGROUND
Madonna (center) and
actress Rosie O’Donnell
(right) attended the
New York City premiere
of A League of Their
Own on June 25, 1992.

A SOFTER IMAGE
Madonna in Paris in 1994 as she promoted Bedtime
Stories, an album on which she worked with artists like Björk.
It was a No. 1 hit on Billboard’s Dance Club Songs chart.

celebrated same-sex love by making costars of

her tour dancers, most of whom were openly gay
men—then a rarity at the movies. (It would be
two more years before Tom Hanks and Antonio
Banderas played a couple—who never kiss on-
screen—in Philadelphia.)
But Truth or Dare was just a slice of the second
decade she dominated. “She’s a phenomenon,”
Warren Beatty said. The actor-director (who
appears in a Truth or Dare cameo as Madonna’s
then boyfriend) cast her as singer Breathless
Mahoney in his 1990 film adaptation of Dick
Tracy. What he got was, in his words, “a huge
personality, diligent and disciplined and a
spectacular dancer and performer” and a smash
soundtrack powered by the No. 1 hit “Vogue.”
The Stephen Sondheim-written ballad “Sooner
or Later” that she sings in the movie earned the
composer an Oscar.
Parallel with her music career, Madonna con-
tinued to knock on Hollywood’s door. Finding
ideal projects proved difficult, though. For every
small miracle (sassy, swing-dancing “All the
Way” Mae Mordabito in 1992’s A League of Their
Own), there was a bomb (1993’s Body of Evidence,
for which she alone should not have to shoulder

MADONNA PEOPLE 53
THE ’90s

EROTICA
Right: Madonna made
“Express yourself don’t
repress yourself” her
motto in the ’90s, which
is evident in this scene
from the set of her 1995
“Human Nature” video.

SOMETHING TO
REMEMBER
Opposite: Madonna
made her videos
cinematic experiences.
Here she filmed 1994’s
“Take a Bow” in Ronda,
Spain, inspired by the
era (if not the geography)
of Evita.

COME ON, VOGUE

Below: Madonna
on the set of her video
shoot for the 1990
smash single.

the blame; Willem Dafoe was a willing costar).

But in Evita (1996) Madonna found an acting role
she could pour all of her talents into. With precision
and authenticity, she brought forth Eva Perón’s cult of
personality. Across Alan Parker’s opulent Broadway
adaptation, she delivered stronger-than-expected
vocals, having prepared at length with composer
Andrew Lloyd Webber. Onscreen she and Antonio
Banderas had so much chemistry they made a tango
in a slaughterhouse sexy. Evita earned some strong
 ‘PEOPLE SEE
EVA PERÓN AS
EITHER
A SAINT
OR THE
INCARNATION
OF SATAN.
I CAN
DEFINITELY
IDENTIFY
WITH HER’
—MADONNA , 1996

reviews, won an Oscar (for Eva’s new song “You Must
Love Me”) and three Golden Globes, including one
for Madonna’s performance. (Two decades later
Broadway powerhouse Patti Lupone, who created
the role onstage, offered a dissenting view, telling
TV’s Andy Cohen she felt Madonna was “a movie-
killer . . . dead behind the eyes.”)
But the Madonna of the ’90s could not be brought
down by dissenters—and there were critics with some
substantial platforms coming for her then.
The Vatican called her Blond Ambition tour “one of
the most satanic shows in the history of humanity.” But
that didn’t stop it from breaking sales records—if any-
thing, it probably goosed the numbers. MTV banned
Madonna’s most erotic clip yet, “Justify My Love,” so
she turned around and sold hundreds of thousands of
copies of it as a video single for $10. By today’s stan-
dards “Justify” no longer shocks (it’s a nursery rhyme
compared with, say, Cardi B’s “WAP”), but decades ago
(Continued on page 59)

MADONNA PEOPLE 55
 THE ’90s

‘I DON’T THINK
OF WHAT
I’M DOING
AS GENDER
SPECIFIC.
I AM WHAT I AM,
AND I DO
WHAT I DO’
—MADONNA , 1990

56
 TRUE BLUE
Madonna made
some new fans when
she crossed paths with
a French rugby
team at the Ritz on
Sept. 30, 1993.

MADONNA PEOPLE 57
 THE ’90s

GRAMMY GOLD
Ray of Light made
Madonna a big winner
at the 41st Grammy
Awards in 1999.
The blockbuster
album propelled her
to four wins, including
Best Pop Album.

58
 HOLLYWOOD NIGHTS
Madonna and then beau Carlos Leon, with whom she had recently welcomed daughter Lourdes,
arrived for EvitaÕs 1996 premiere in Los Angeles (left). The next year,
Madonna won a Golden Globe for Best Actress in a Leading Role—Musical or Comedy (right).

(Continued from page 55) a then-34-year-old Madonna released a new LP,

Madonna was often called upon to explain herself.
“I grew up feeling incredibly repressed,” she told
People at the end of the decade. “My rebellion hap-
pened, instead of in my teens, when I was 30. I just
wanted to go, ‘Don’t tell me what to do just ’cause I’m
a girl. Don’t tell me I can’t be sexual and intelligent
at the same time.’ ”
Madonna emerged from every uproar and puri-
tanical condemnation more popular than ever—and
even more determined to keep stirring up tumult by
brazenly confronting those straitlaced values. But
that wouldn’t always be the case. In October 1992,
Erotica, and a coffee-table book titled Sex filled with
arty yet graphic photos by Steven Meisel.
The Sex book, spiral-bound between metal covers,
featured loads of nudity, soft takes on S&M culture,
some toe-sucking and plenty of stars: actress Isabella
Rossellini in drag, rapper Big Daddy Kane
and model Naomi Campbell in a mock threesome with
Madonna, and (because it was still the ’90s) Vanilla
Ice. Critics savaged it. Eager fans snapped up all 1.5
million copies in a few days, and the now-out-of-print
book became a collector’s item of the highest order.
(Continued on page 62)

MADONNA PEOPLE 59
 ‘EVERYTHING
WE DO BECOMES
AN EVENT’
—JEAN PAUL GAULTIER,
ON HIS COLL ABOR ATION WITH
MADONNA , 1990

60 MADONNA PEOPLE
 FASHION FEVER
DREAMS
With French designer
Jean Paul Gaultier, who
created Madonna’s
Blond Ambition tour
costumes (including the
famous cone bras), at
the 1994 launch of
Gaultier’s perfume.
Inset: Gianni Versace
gave the bridal bouquet
to Madonna at one of his
shows in 1995.
 ‘THE THOUGHT
I KEPT HAVING WAS,
“MY GOODNESS,
IF IT WASN’T FOR
ME, MADONNA
WOULD BE
WEARING
SOMETHING ELSE” ’
—ARTHUR GOLDEN ,
AUTHOR OF 1997 ’S MEMOIRS
OF A GEISHA

RED ALERT
Madonna performed
“Nothing Really
Matters” from Ray
of Light at the 41st
Annual Grammy Awards
on Feb. 24, 1999.

(Continued from page 59)
Narrated by Madonna as dominatrix alter ego
Mistress Dita, the album Erotica generated its own
heat. And not just for naughtiness. In the past Ma-
donna cherry-picked pop styles to make excellent
but hodgepodge LPs. Erotica streamlined the sonics
by channeling the pulsing, pounding and thumping
underground dance music. The house beats paired
nicely with Madonna’s sex-positive, sex-forward,
sex-all-the-time vibe. But coos, commands and
breathy vocals on top of atmospheric synthesizers
and computer clicks somehow left some listeners
cold: Erotica peaked at No. 2, a bewildering miss for
a woman accustomed to being on top.
When she stopped by Late Show With David
Letterman on March 31, 1994, and dropped 14
f-bombs, many portrayed her not as smart, sexy
or shrewd—but as desperate. Later that year she
released Bedtime Stories, a lush LP infused with mel-
low neo-soul and electro-pop. Despite some critical
love for collaborations with Björk and a crew of star
producers that included Babyface, the album stalled

62 MADONNA PEOPLE
 THE ’90s

RED CARPET
In a Jean Paul Gaultier
outfit, Madonna left the
Cannes Festival Palace
in France after a
screening of her Truth or
Dare documentary on
May 13, 1991.

63
 at No. 3. Still, it got her mental state across: “Did I
say something wrong? Oops, I didn’t know I couldn’t
talk about sex,” she sings in “Human Nature.”
If Bedtime Stories showed a softer side, it may have
been that her priorities were shifting. After split-
ting from Sean Penn and a few A-list romances, she
enjoyed a surprising romance with personal trainer/
64 MADONNA PEOPLE
actor Carlos Leon. On Oct. 14, 1996, their daughter
Lourdes Maria was born, and everything changed.
“This is the greatest miracle of my life,” Madonna
told People. The new mom would be only briefly out
of the spotlight. And then in 1998 Madonna returned
with the album Ray of Light, singing, “Now that I
am grown/ Everything’s changed/ I’ll never be the
 THE ’90s

THIS IS YOUR
LIFE (IN DRAG)
The star made
friends with some
Madonna-esque drag
performers as well as
Lauryn Hill and Paul
McCartney (below)
at the 1999 MTV
Video Music Awards in
New York City.

‘I FEEL JUST AS HUNGRY

TODAY AS I DID
THE DAY I LEFT HOME’
—MADONNA , 1999

same/ Because of you,” on the track “Nothing

Really Matters.”
She had changed, of course. If she had spent
the ’80s in pursuit of fame and most of the ’90s
chasing controversy through the marriage of
sex and religion, the Madonna who entered the
2000s was focused more on family—and love.

65
 THE ’90s

66 MADONNA PEOPLE
BACK TO
THE BOX
OFFICE
HITS OR MISSES,
MADONNA SWUNG
FOR THE FENCES
The singer appeared in a
wide range of comedies and
dramas (clockwise from
opposite): Dick Tracy (1990,
with, among others, Warren
Beatty in yellow and Al
Pacino, seated), A League of
Their Own (1992), Body of
Evidence (1993, with Willem
DaFoe), Girl 6 (1996, with
Spike Lee and Theresa
Randle), Shadows and Fog
(1991, with John Malkovich),
Dangerous Games (1993,
with Harvey Keitel) and Four
Rooms (1995, with a cast
that included Tim Roth, in
hat, and Antonio Banderas),
a New Years comedy at a
Los Angeles hotel.

67
 1. DESPERATELY
SEEKING SUSAN
(March 29, 1985)
Lying in a trashed
Atlantic City hotel
room, Madonna invents
the selfie with a Polaroid
camera. This is how
director Susan
Seidelman introduces
her title character in
Desperately Seeking
Susan. Some critics said
Madonna succeeded in
the role of a nightclub
gypsy by playing herself;
others said it announced
her as an actress. Who’s
right? Who cares? It is
an unmissable debut.

ICONIC
DON’T-MISS
MOMENTSA W AY F R O M T H E C O N C E R T S TA G E ,
MADONNA HAS TURNED IN SOME ESSENTIAL
P E R F O R M A N C E S F R O M S N L T O B R O A D W AY

68 MADONNA PEOPLE
 2

2. INTERVIEW ON AMERICAN BANDSTAND, 1984

Alone on the Bandstand dance floor—bouncing, twisting and
clearly lip-synching to “Holiday”—Madonna oozed charisma.
After the performance, which aired Jan. 14, 1984, host Dick
Clark tried to start his interview, but the giddy crowd wouldn’t
stop screaming. When Clark finally got to ask her what her
dreams are, the 25-year-old star bit her lip, halfway between
adorable and unstoppable, and replied: “To rule the world.”

3. TRUTH OR DARE, 1991

Madonna’s public persona could eclipse the fact that she is an
actual person. Alek Keshishian’s documentary Truth or Dare
was a fascinating reminder. It began as a concert film, but life
behind the scenes with Madonna and her dancers and singers
proved as compelling a spectacle as their show. She let cameras
capture her suffering with laryngitis, enduring an unrequited
crush on Antonio Banderas and awkwardly meeting up with,
then dismissing, a childhood friend. A producer of the film, she
might have nixed those scenes. But no. As her then beau
Warren Beatty put it: “She doesn’t want to live off-camera.”
3

4. MADONNA DEBUTS ON BROADWAY, 1988

Alongside veteran actors Joe Mantegna and Ron Silver, Madonna
proved (again!) she can play more than herself. In its review of
Speed-the-Plow, David Mamet’s Tony-winning satirical takedown
of Hollywood culture, The New York Times cheered Madonna’s
performance as an alluring secretary, describing it as “intelligent,
scrupulously disciplined comic acting.”

69
 5. SATURDAY NIGHT LIVE, 1992
Madonna and Roseanne Barr joined Mike
Myers for his “Coffee Talk With Linda
Richman,” a show, “dedicated, as ever, to
Barbra Joan Streisand.” As they kvelled about
their icon and her Oscar-nominated film The
Prince of Tides, they got an unexpected visit
from Streisand herself. “Hello, gorgeous.”

6. “VOGUE” AT THE VMAS, 1990

The video for “Vogue” featured 1940s
movie glamor and voguing, a dance born of
Harlem drag balls. She could have re-created
it onstage, but Madonna and crew instead
turned up in Marie Antoinette finery—equal
in artifice but wholly new and surprising.

7. EVITA, 1996
The part was not written for her. (Elaine Paige created it onstage.) She wasn’t a Broadway
belter. She didn’t even have a great track record at the box office. But somehow
Madonna was a perfect movie fit for Eva Perón, two oft-maligned icons of excess and allure.
It remains her greatest scripted performance.

70
 ESSENTIAL PERFORMANCES

8. SUPER BOWL XLVI, 2012

This halftime show packed a lot into
12 minutes: Spartan soldiers, break-dancers,
parkour masters, drum lines, an impish
slackliner and musical assists from
LMFAO, M.I.A., Nicki Minaj and Cee Lo
Green. Amid it all Madonna, in towering
thigh-high boots at 53, made a medley
of five hits look effortless.

9. “LIKE A PRAYER,” MET GALA, 2018

It’s hard to thrill a jaded fashion crowd.
But that hooting and hollering you
heard was coming from an elated group
that included Rihanna, Cardi B and Kim
Kardashian, who fangirled out for
Madonna’s unannounced performance,
a mash-up of Gregorian-esque chants,
modern electro-pop and Leonard Cohen.
8

MADONNA PEOPLE 71
 THE 2000s

O N A J O U R N E Y O F S E L F - D I S C O V E R Y T H AT
I N C L U D E D N E W FA I T H A N D A C H A R I T Y,
M A D O N N A E X PA N D E D H E R FA M I LY A N D E A R N E D
TH E R ECO G N ITI O N O F H ER RO CK PEER S
By JED GOTTLIEB

“i’ve gone through all my sexual rebellion,” Madonna told People in 2000.
“I worked it out of my system.” In place of sexual rebellion, there was now a
devoted yoga practice, the study of Kabbalah mysticism and mothering her young
daughter Lourdes. “She’s so much calmer, so much more centered than she used
to be,” observed her friend Rosie O’Donnell.
She was also, in her 40s, back on top professionally. Ray of Light married layers
of buzzing techno, ambient-humming synthesizers and flourishes of Middle East-
ern and Indian musical motifs, with newly introspective lyrics. “I traded fame for
love without a second thought/ It all became a silly game, some things cannot be
bought,” she sings on the opening track, “Drowned World/Substitute for Love.”
Ray of Light sold more copies than any of her ’90s studio albums and earned four
Grammy Awards. Throughout her most personal and intimate reinvention, she
remained in complete control. “At the Grammys it was a little implicit that there
was a guy behind it all,” Ray of Light coproducer William Orbit told Rolling Stone
in 2000. “And it’s really far from that. The one with all the equipment is assumed
to be pressing all the buttons. She presses all the buttons.”

72 MADONNA PEOPLE
 “DON’T TELL ME TO STOP”
In 2001 Madonna threw a
Madison Square Garden party,
ringing in her third decade of
pop dominance in the town that
gave her a first break. The tour
featured 2000’s album Music.
73
 FILM FRIENDS AND LOVERS
Madonna and Rupert Everett as BFFs who have a baby in The Next Best Thing, 2000. Right: Guy Ritchie’s 2002 remake of Swept Away
was a stylish flop; Madonna starred with Adriano Giannini (son of Giancarlo Giannini, the male lead in Lina Wertmüller’s 1974 original).

In her personal life, more change. In 1999, at a
party thrown by her friends Sting and wife Trudie
Styler, Madonna had met British movie director Guy
Ritchie, who was riding high on his cult gangster noir
hit Lock, Stock and Two Smoking Barrels. “My head
didn’t just turn, my head spun round on my body,”
said Madonna. “I was taken by his confidence. He was
sort of cocky but in a self-aware way. He’s a risk-taker,
and he’s got a hungry mind.” An intense romance led
the couple to marry in late 2000, months after the
birth of their son Rocco. The new parents nested in
London, where Madonna, recorded 2000’s Music,
which came out in September—in between the baby
and the wedding. (Madonna is nothing if not an
admirable multitasker.) Perhaps missing home, the
expat star focused on Americana: Cowgirl hats and
acoustic guitars mashed up with club-ready European
techno. Around the same time, she recorded a cover of
Don McLean’s “American Pie.” With younger artists
from Britney Spears to Christina Aguilera to Destiny’s
Child nipping at her heels on the charts, Madonna,
as a critic for the Austin Chronicle put it: “shimmies
into get-the-hell-out-of-Dodge duds, cocks her index
finger like a gun and blows away the competition.”
Next she prepared for the 2001 Drowned World
tour, her first since 1993’s the Girlie Show. The lineup
would lean heavily on material from Ray of Light and
Music and featured Madonna playing guitar onstage
for the first time. Thrilled to see a concert of new
songs, fans gobbled up tickets at a feverish pace; five
nights at New York’s Madison Square Garden went
quickly, and the younger stars were put on notice:
Madonna wasn’t giving up her pop queen crown easily.
While 2003’s American Life disappointed (with fans
and sales numbers), 2005’s Confessions on a Dance
Floor bounced through a full hour of joyous disco jams.
The single “Hung Up” became her biggest hit by hitting
No. 1 in 41 countries. Her films were flailing, but her
concerts remained a hot ticket. In 2006 her Confes-
sions Tour became the all-time top-earning tour by a
female artist. Three years later Sticky & Sweet set the
record as the highest-grossing run ever by a solo artist.

74 MADONNA PEOPLE
 THE 2000s

‘THE IDEA WAS THAT THE WIFE

AND I WOULD MAKE SOME SASSY
LITTLE ART MOVIE, BUT WE
GOT THE S--- KICKED OUT OF US. . . .
IT’S A GOOD FILM. I’M LEFT
SHAKING MY HEAD’
—GUY RITCHIE, 2002

75
 THE 2000s

HOMEGROWN
Promoting her 2003 album
American Life, Madonna
performs a set (with guitarist
Monte Pittman) at New York’s
Tower Records in 2003.

76
 PAIR OF QUEENS
The Queen of Pop met Elizabeth II at London’s Royal Albert
Hall in 2002 for the premiere of the James Bond movie Die
Another Day, for which Madonna recorded the theme song.

During her travels Madonna visited Malawi, a

developing African country in which more than
half a million children had been orphaned by the
HIV/AIDS epidemic. She founded a charity, Rais-
ing Malawi, to assist kids there, and in 2006 she
and Ritchie adopted a son, David Banda. (David’s
mother had died from childbirth complications;
his father, Yohane Banda, who had placed him in
an orphanage, met with Madonna and Guy Ritchie
and consented to the adoption.) The story made
headlines: Had a celebrity flouted local adoption
laws by not establishing residency? Did David’s
father understand the arrangement? “I expect
‘IT WAS LIKE A to be given a hard time about many of the things
WHOLE NEW WORLD. I do. I know they are provocative, and I prepare
I’M A L ATE BLOOMER, myself,” said Madonna in response to the dustup.
BUT HEY, BETTER “But I did not expect the media, the government
L ATE THAN NEVER’ or any human rights organizations to take a stand
—MADONNA , ON against me trying to save a child’s life.” The adop-
LEARNING THE GUITAR tion was finalized, and three years later, after she

MADONNA PEOPLE 77
 THE 2000s

‘[EARLY ON] I THOUGHT EVERYTHING WAS

ABOUT HAVING EVERYONE ADORE
YOU. . . . SOMEHOW I FELL INTO MUSIC’
—MADONNA , 2003

READY FOR HER CLOSE- UP

Madonna, who had recently released Confessions on a Dance Floor, thrilled a Coachella festival
crowd in Indio, Calif., 2006. Below: In New York City she made a new fan, 18-month-old
Jeremy Zorek, at a reading and signing of her bestselling children’s book The English Roses, 2003.

and Ritchie divorced, Madonna would return to

Malawi, where she was building a girls’ school, to
adopt a daughter, Mercy James. “Helping people
is like tattoos,” Madonna would tell People. “Once
you get a tattoo, you keep getting them. It’s addict-
ing. You see the difference you’re making in one
person’s life, so what’s the big deal if I help one
more person and one more person?”
Perhaps hoping to reach more kids, Madonna
added children’s author to her résumé by writing
a series of storybooks. The first, titled The Eng-
lish Roses, topped the The New York Times Chil-
dren’s Picture Books bestseller list. Of course she
was still Madonna and didn’t forget the grown-
ups. She wrote and directed her first movie, Filth
& Wisdom, about three London flatmates: an
aspiring Ukrainian rock star who moonlights as
a dominatrix, a dancer earning rent by strip-
ping and a pharmacist who longs to help African
children. Filth debuted at the 2008 Berlin Film
Festival and earned the sorts of reviews that
would not necessarily inspire a woman to quit

78
 WORKING IT
Madonna and Missy
Elliott teamed up for a
fall 2003 campaign for
the Gap (above).

MADONNA PEOPLE 79
 A FILM EVERYONE
CAN SEE!
Madonna, Guy Ritchie
and children Rocco and
Lourdes arrive at the 2007
London premiere of
Arthur and the Invisibles,
in which Madonna
voiced the character of
Princess Selenia.

80
 THE 2000s

ROCK STAR
Madonna invited Justin Timberlake to join her on her 2008 hit
about climate change “4 Minutes.” He returned the favor,
inducting her into the Rock and Roll Hall of Fame in 2008.

her day job, which naturally Madonna did not.

She released Hard Candy, her 11th studio LP and
seventh to reach No. 1, in 2008. With its single
“4 Minutes,” she surpassed Elvis Presley to become
the artist with the most Top 10 singles—the song
was her 37th to make that Billboard list. She inked
a $120 million deal with concert promoter Live
Nation to handle all her future music and music-
related businesses. At the same time, in her first
year of eligibility, she was inducted into the Rock
& Roll Hall of Fame. She was introduced by Justin
Timberlake in an innuendo-filled speech. (Madonna
was always “a woman on top,” he noted to chuckles.) less, that I was chubby, that I couldn’t sing, that I was
But the artist herself seemed genuinely moved by a one-hit wonder. They inspired me because they
the vote and from the podium thanked the many made me question myself repeatedly, pushed me to
people who had been her champions—and those who be better, and I am grateful for their resistance.”
had been her harshest critics. Through the years, At 49, Madonna remained the world’s biggest pop
she said, people had charged that she was “talent- star, while also becoming a legend.

MADONNA PEOPLE 81
 ‘I REMEMBER THINKING, “I HAVE
SO MUCH, AND I DON’T
FEEL LIKE I’M DOING ENOUGH” ’
—MADONNA , ON HER REASONS
FOR STARTING R AISING MAL AWI

82 MADONNA PEOPLE
 THE 2000s

USING HER SPOTLIGHT

Madonna at the premiere
of her documentary
I Am Because We Are,
which brought attention to
the AIDS crisis in Malawi,
the African nation where
she has focused her
charitable work.

83
 “BITCH, I’M MADONNA”
The Queen of Pop has
earned the right to do
(and sing) what she wants.
Often what she wants
to do is dance, as at this
2022 DiscOasis event
in New York City.

84
 MADONNA
TODAY

H AV I N G R E A C H E D T H E L I F E -A C H I E V E M E N T E R A ,
M AD O N NA ACCEPTED TH E ACCO L AD E S WITH
G R AT I T U D E — A N D J U S T K E P T O N
By JED GOTTLIEB

“the most controversial thing I have ever done is to stick around,”

Madonna said at an event honoring her as Billboard’s 2016 Woman of the Year.
She had entered the era of career-capping accolades, at a time when many art-
ists slow down, reflect and appear in public mainly to accept their laurels.
A generation younger than the still-at-it Rolling Stones, Madonna, then 58,
was nonetheless grateful to have come that far. “Michael [Jackson] is gone,” she
told the crowd. “Tupac is gone. Prince is gone. Whitney is gone. Amy Wine-
house is gone. David Bowie is gone. But I’m still standing. I’m one of the lucky
ones, and every day I count my blessings.”
As a young woman with a few hits, Madonna had told Dick Clark in 1984
that she planned to “rule the world.” She made good on her promise and,
in an industry that values youth and novelty above all, endured through a will
to hold the spotlight, even as stars from Britney to Beyoncé to Billie Eilish came
up in her wake.
“I felt like I wanted to follow the footsteps of Madonna and be a powerhouse and
have my own empire,” Beyoncé said on why she founded her own entertainment

MADONNA PEOPLE 85
 ‘I WOULD
LIKE TO THANK
MY MOTHER. . .
THIS IS THE
STORY OF THE
JOURNEY OF
A FEMALE SOUL’
—MADONNA , AT THE
NEW YORK CIT Y
PREMIERE OF W.E .

86 MADONNA PEOPLE
 MADONNA TODAY

and management company. Many newer art-

ists have sung her praises and credited her with
inspiring their own paths. Adele said Ray of Light
influenced her writing on 25. Taylor Swift pointed
to Like a Prayer as helping to create 1989. One fan,
Nicki Minaj, literally went on record with her feel-
ings, declaring, “There’s only one queen, and that’s
Madonna, bitch” at the end Madonna’s track “I
Don’t Give A,” which featured the hip-hop star.
While she accepted a new generation’s debts of
gratitude, Madonna still preferred to compete with
those acts for chart positions and pop primacy. In
2012 alone, she released her fifth-consecutive No. 1
album, MDNA, and a record-extending 38th Top
10 single, “Give Me All Your Luvin’. ”
She was canny about appearing alongside
younger artists, to both mix it up creatively and
broaden her reach. At the Super Bowl she shared
the stage with Minaj, M.I.A. and others. Together
they drew more viewers than the game itself.
For 2015’s LP Rebel Heart, she worked with
Kanye West, Diplo and more new collaborators,
earning some appreciative nods from critics, if not
the sort of sales she’d grown used to enjoying. Still,
the corresponding tour found Madonna in a light-
er mood onstage—a confetti canon and a ukulele
figured into her act—while TV audiences caught
her gamely promoting the album by twerking in
the passenger seat during “Carpool Karaoke” on
The Late Show with James Corden.
Her 14th studio album, 2019’s Madame X,
recorded in Lisbon, where she has a home, was
embraced as a successfully oddball departure, mix-
ing Latin rhythms with techno. A reviewer for The
(Continued on page 91)

DIRECTOR’S CHAIR
In 2010 Madonna helmed the
historical romance W.E.
with James D’Arcy and
Andrea Riseborough
(of To Leslie) as the Duke
and Duchess of Windsor.
MADONNA TODAY

POP ROYALTY
Rihanna, Alicia Keys,
Madonna and Beyoncé
show some love at
a 2015 launch party for
streaming service Tidal.

GET TOGETHER
Back row, left to right: Debi Mazar, Gloria
Steinem, Madonna and (front row) Amy
Schumer attended the Women’s March on
Washington on Jan. 21, 2017.
 FEARLESS
Taylor Swift lends a hand
on Madonna’s single
“Ghosttown” during the 2015
iHeartRadio Music Awards
at the Shrine Auditorium
in Los Angeles.

MADONNA PEOPLE 89
 MADONNA TODAY

OPEN YOUR HEART

Madonna with
two of her kids, David
and Mercy James,
in 2013 at a classroom
at Mkoko Primary
School, one of the
schools her Raising
Malawi organization
helped build.

‘IT’S INEXPLICABLE.
IT’S LIKE SAYING,
“ WHY DO YOU FALL
IN LOVE WITH
THE PEOPLE YOU
FALL IN LOVE WITH? ” ’
—MADONNA , ON BONDING
WITH HER CHILDREN

90
 TEAMWORK
Madonna and her children Mercy James (left) and
David Banda (right) with BuildOn director Maurice Muchene.
BuildOn worked with the singer’s charity Raising Malawi to
build schools in the country.

(Continued from page 87)

Guardian called it “her most bizarre album ever”
even as he awarded it four stars.
During this period she also became a mother of
six, by adopting twins Stella and Estere from Ma-
lawi. There in 2017 she opened the Mercy James
Centre for Pediatric Surgery and Intensive Care,
the country’s first children’s hospital. The ribbon
cutting was a family effort. Son Rocco, a budding
artist, painted a mural at the site. David performed
a dance with boys from a local school, and daugh-
ter Mercy—the facility’s namesake—gave a moving
speech. (Oldest child Lourdes was away at col-
lege, “but she was there in spirit!” Madonna said.)
She seemed proud but unconcerned with them
emulating her professionally. Rather, she told
People at the time, “I want my kids to be loving,
decent, compassionate human beings. I try to set a
good example. But it’s been a roller-coaster ride.”
She is, it should be noted, an icon also of work-life
balance. That song with the shout-out from Nicki
Minaj finds Madonna singing: “Wake up, ex-wife/
This is your life/Children, on your own/Turning
on the telephone/Messages, manager/No time for
a manicure/Working out, shake my ass/I know
how to multitask . . .”
As if to prove the point, in January 2023,
Madonna announced the Celebration Tour. She
surprised fans with the news via a star-studded
video—Lil Wayne! Jack Black! Bob the Drag
Queen!—that coyly riffed on the Truth or Dare
documentary. The black-and-white clip closed
with Amy Schumer saying, “Madonna, I dare you
to do a world tour!” Days after the video, hundreds
of thousands of Madonna lovers rushed to ticket-

MADONNA PEOPLE 91
 MADONNA TODAY

FAMILY ACT
Madonna and son Rocco,
then 12, perform on opening night
of the 2012 MDNA North America
tour in Philadelphia.

92
 BRING THE KIDS
Above: with son
David at the 2014
Grammys. Top right:
with daughters Estere,
Mercy and Stella at the
opening of a hospital
the star funded in
Malawi, 2017. Right:
with Rocco and Lourdes
at a 2022 Tom Ford show.
ing sites to sell out three dozen dates. The shows were
later postponed when Madonna underwent treat-
ment for an infection.
In June she dropped a new collaboration with the
Weeknd and Playboi Carti, “Popular,” followed by a
duet with Sam Smith, “Vulgar.” The singles gave her
a Billboard chart presence in five decades. Add that
to the pile of milestones: highest-grossing female
touring performer of all time and bestselling female
recording artist. Not to mention three—count ’em!—
ex-communications by the Vatican (at least by her esti-
mation in 2022, when she reached out to Pope Francis
on Twitter). Madonna, who turns 65 in 2023, earned
the right to take a holiday. She has spent 40 years writ-
ing, recording and performing music that some might
dismiss as disposable pop. But at each stage she has
served sharp hooks and sing-along choruses, along with
bursts of wisdom, defiance and inarguable genius that
you can dance to.
She has outlasted critics who called her a passing
craze. She defied sexism and, later, the double-whammy
of sexism and ageism. At the 2023 Grammys to intro-
duce the first openly transgender winner (Kim Petras),
Madonna felt the wrath of trolls talking about her ap-
pearance. On Instagram she railed against “a world that
refuses to celebrate women past the age of 45 and feels
the need to punish her if she continues to be strong-
willed, hardworking and adventurous.” Then she just
kept on, as she had since her early days when she slid
her personal philosophy into a track on the Like a Virgin
album singing: “It doesn’t matter who you are/ It’s what
you do that takes you far/ And if at first you don’t suc-
ceed/ Here’s some advice that you should heed/ You get
up again, over and over . . .”
MADONNA PEOPLE 93
 MADONNA TODAY

‘IT WAS A WONDERFUL

FAMILY REUNION
AND QUITE THE FASHION
THROWBACK’
—EYOB YOHANNES, ST YLIST FOR
MADONNA’S 2018 MET GAL A LOOK

CONFESSIONS
Madonna and designer Jean
Paul Gaultier at the 2018 Met
Gala when the theme was
“Heavenly Bodies: Fashion and
the Catholic Imagination.”

94 MADONNA PEOPLE
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95
 WE’VE GOT A GREAT
SHOW FOR YOU . . .
In on the joke, Madonna used her first time hosting Saturday Night Live,
in 1985, to send up how prying eyes and paparazzi swarmed her
wedding that year to Sean Penn. (The groom was played in “home
videos” by then-SNL cast member Robert Downey Jr.) Madonna also performed
and capped her monologue by quashing a rumor: “I’m not pregnant.”

96 MADONNA PEOPLE
 The ’80s: Desperately
Seeking Susan
(with Rosanna Arquette).

The ’90s:
the Blond
Ambition tour.

MADONNA THE QUEEN OF POP IN 130+ PHOTOS

The Story of Her Rise and 40-Year Reign • More Than 50 Chart Hits
• Her Style & Dazzling Shows PLUS Life Offstage: a Mom to Six

Today: on tour,
new music.

The 2000s:
“American Pie.”