We start in 1984, the year after she exploded onto the scene with her debut album, “Madonna”.
The “Like a Virgin” years
From “Madonna and Teena Marie: The Voice, Its Power, and Its Subtleties,” by J.D. Considine, published November 24, 1984:
Her voice isn't powerful, but it is remarkably expressive, allowing her to convey a depth of personality that goes well beyond the specifics of her material. On the title song of her new album, "Like a Virgin," she neatly skips past the lyrics' simple metaphor of being reborn through true love and, with a nudge and a wink, transforms it into a delicious bit of naughtiness.
Part of the trick is in the way she uses her voice, applying a girlish coo for such lines as "Like a virgin, touched for the very first time," but swelling to full power when she sings, "Yeah, you made me feel I've nothing to hide." Because Madonna allows us to hear the woman behind the girl, the conceit of the lyric becomes believably charming.
Jam out to a Material Girl Spotify mixtape here.
Madonna’s rising career
From “Personalities,” by Chuck Conconi, published May 13, 1987:
It may not come as a stop-the-presses surprise to anyone, but a publicist for Madonna says her marriage to the bad-tempered Sean Penn is rocky. The couple apparently have not legally separated and are attempting to work things out. Penn is presently having legal problems and could be sentenced to six months in jail for violating a probation order by punching a film extra in the face ...
Madonna later said of her marriage to Penn: “I was completely obsessed with my career and not ready to be generous in any shape or form.” The year their divorce was finalized, she released “Like a Prayer”:
The provocative years
Watch her interview with David Letterman in 1994, in which she makes disparaging comments about Charles Barkley, encourages Letterman to sniff a pair of her underwear that she had brought him as a gift, and drops multiple f- and s-bombs, here.
From “Man guilty of stalking Madonna” by wire reports, published January 9, 1996:
A man who threatened to slice Madonna's throat from ear to ear was found guilty today of stalking the pop star... A jury convicted drifter Robert Dewey Hoskins on all five counts -- one count of stalking Madonna, three of making threats against her and one of assaulting her bodyguard at the star's Hollywood estate... On Thursday, Madonna's bodyguard described how he shot and wounded Hoskins, who climbed the wall around the pop star's estate, jumped into a pool and threatened to kill her.
The “Ray of Light” years
From “Madonna and DiFranco: Two CEOS diversify,” by Richard Harrington, published March 1, 1998:
Such a transformation makes sense. Where the material on "Bedtime Stories" seemed to shift Madonna's focus from sex to romance, "Ray of Light" represents a further evolution from scandal to serenity, from materialism to maternalism, and from self-centeredness to selflessness (she's been doing a lot of reading in Hinduism and Kabbalah, the Jewish mystical tradition).
This is Philosophical Madonna who, approaching 40, still touches lightly on such familiar topics as romantic obsession, sexual desire and the price of fame, but also has thoughts on spiritual catharsis, enlightenment, positivity and karma. She even sings a whole song in Sanskrit (the ecstatic "Shanti/Ashtangi").
Overtaken by Britney
From “Madonna: Saddle Up!” by Bill Werde, published on November 7, 2000
Before the show, beneath spotlights and a pulsing marquee that blared MADONNA in enormous red letters, the singer's fans squawked her early hits for the television crews... "I'm so happy to be onstage again," she told the crowd. "But I'm nervous. It's been a while." The singer hasn't done a full tour since 1993, and opted Sunday night for the relative intimacy of Roseland, which holds just 3,000 people. She has expressed a preference to return to the small clubs she played early in her career, for a tour that is very tentatively planned for next year.
In a gesture that seemed deliberately ambiguous, Madonna took off her jacket to reveal a sleeveless black T-shirt emblazoned with "Britney Spears" in sequins. Later, Britney still on her mind, she dedicated a performance of her gentle ballad "What It Feels Like for a Girl" to the reigning teen queen of pop. Madonna closed the night--and drew deafening cheers--with a performance of the album's title song, which is also her current hit single.
From “Behold the Immaterial Girl,” by Robin Givhan, published April 6, 2008:
The pop star is almost 50, which seems to be the leitmotif of the accompanying story -- as if we are compelled to check in with Madonna to see how she is handling each turning point in her life. Over the years, the magazine has dutifully recorded in words and elaborately styled photos Madonna's early success, her failed first marriage, the publication of "Sex," her hankering for film stardom, motherhood, Malawi and, of course, her magnificent physical upkeep...
Shockingly, Madonna has gotten boring. Our Madonna -- the rule-breaking, professional provocateur, endearing egoiste, subject of countless maligned college courses on postmodern female sexuality, patron saint of a generation of young women who relied on pop culture psychobabble to excuse their exhibitionist tendencies -- has become a cliche. She's just another aerobicized pop singer with a cause.
Madonna should not have French-kissed Britney Spears. She shouldn't have talked so much about yoga and her macrobiotic diet, and she certainly shouldn't have discussed either topic with that distracting British accent... We have nothing left to ask Madonna.
Still got it
From “The Age of Madonna: Touched for a Very Long Time,” by Hank Stuever, published August 10, 2008:
Madonna, OMG, you are 50...You have said again and again that you never read newspapers or magazines, even though you are always in newspapers and magazines, so this is in some way wasted space and energy... Then again, she needn't be present for us to talk about her. This has always been the key element to how Madonna has spent half her life, deliberately deaf in the center of the buzz. Madonna turning 50 is not about Madonna. As ever, it's about the rest of us, who are always caught watching Madonna do whatever it is Madonna currently does, even if when whatever Madonna is doing is nothing more than growing old.
"So what are you going to do when you get older, Madonna? Are you going to be going on 50 and still get up onstage and shake your booty, like Cher? What happens when your body goes?"
"Then I'll use my mind."
-- From an interview with Madonna, in Vanity Fair, October 1992