On September 17 2001, Madonna appeared on the cover of People magazine as part of the Best and Worst Dressed feature.
People magazine had this to say about Madonna’s great fashion choices in 2001:
Madonna wore midriff-baring Dolce & Gabbana cowgirl pants to Europe’s MTV Music Awards last fall—just three months after giving birth to son Rocco. Britain’s Times later praised the star for baring “her potbelly” during her concert tour, declaring, “The truly hip are taking a leaf out of Madonna’s book and learning to love their tummies.”
On August 29 2005, Madonna appeared on the cover of People Magazine with the caption: Bone Breaking Fall.
Madonna had planned to celebrate her 47th birthday on a warm summer afternoon at her country home outside London, relaxing with her husband and children and horseback riding with her assistant.
And then: boom.
On Aug. 16 the singer took a spill on an unfamiliar horse, suffering three cracked ribs and a broken collarbone and hand. Her husband, Guy Ritchie, drove her to a local hospital, where she was treated and released a few hours later. Fortunately she’s almost finished wrapping up her new album, which she shot cover art for last Thursday and is due out in November. That said, “I’m sure she’ll be very restless,” says rep Liz Rosenberg. “She’s usually doing lots of things at once: Pilates, riding her bike. I think it will be tough on her.” At the very least, she can count on the neighbors to pull her a sympathetic pint or two. “She is well-liked by the locals round here,” says Tim Birks, landlord of Madonna’s local pub the King John Inn. “A lot of people will be wishing her a speedy recovery.” So will she get back on the horse and ride again? “Knowing her, she’ll be riding next week,” says Rosenberg. “She is a fearless girl.”
On July 27 1992, Madonna was featured on the cover of People magazine and in a feature article about the previous 50 years of teen idols.
Here’s a snippet of what People had to say about Madonna in 1992:
Not Just a Mirror of the Times, Madonna Is a Hall of Mirrors: Temptress, CEO, Atomic Blonde, Fatal Attraction—She Struts a Multitude of Selves Across the Stage – From Brando to Axl, the boys have always had somebody to act out their fantasies of rebellion and stand in for their forbidden selves. Then, in 1984, the girls got Madonna. So what if she had a Betty Boop voice and a smidgen of fat around her navel? She also had lyrics that would have made a black-and-white cartoon blush scarlet. “Unlike the others, I’ll do anything,” she sang in the video Burning Up: “I’m not the same/ I have no shame.” No wonder the nuns at her Michigan grade school used to tape her smart mouth shut. Top it off with clothes that seemed hijacked entirely from Frederick’s of Hollywood. Madonna was the material girl all right, and the material she paraded was spandex, Lycra and nylon net. For millions of teenagers, Madonna was the girl of their disobedient dreams. She had power; they had none. She was free, while they still needed Mom’s permission to stay out past 10. Madonna could afford to call herself a boy toy. This was one puppet who pulled her own strings. Her ambition had muscles; her will had the glint of chrome. Susan Seidelman, who directed Madonna in her first hit film, Desperately Seeking Susan, understood her appeal: “Funkiness mixed with amazing confidence—that’s a real powerful combination, especially for teenage girls.” For some big boys too. Did Sean Penn give her trouble? She dumped him like a smart cookie shaking off a crumb. Warren Realty was the permanent playboy? A few months with Madonna and he went running for the quieter life of wedded bliss—with another woman. “I’m tough, ambitious, and I know exactly what I want,” Madonna once said. “If that makes me a bitch, OK.”
On July 14 2008, Madonna and Guy Ritchie were featured on the cover of People Magazine with the caption: “Madonna & Guy Ritchie – Is It Over?”
Here’s a snippet of the article inside by Joe Artolomeo:
For the past five months, it’s been the same story: While Madonna is on one continent making music, working on her Malawi documentary or planning her upcoming tour, her husband, Guy Ritchie, is in another part of the world tending to his own needs. Every few months they reunite—for a photo op, at least. The weekend of June 28 was no different. Madonna was in New York City taking a break from rehearsals to attend services at the Kabbalah Centre with her kids Lourdes, Rocco and David; meanwhile, in London Ritchie was also attending Kabbalah services and spending time with family friend Trudie Styler. On Monday, June 30, he boarded a flight bound for New York City—and his wife. This time the reunion had a sense of urgency. The British press had spent the past five days reporting that Madonna, 49, and Ritchie, 39, had consulted separate divorce lawyers (she chose Fiona Shackleton, who represented Sir Paul McCartney, said The Times and the Daily Mirror), a story that had first surfaced in early June. They pointed out that neither was wearing a wedding band and noted that during their last public appearance at the Cannes Film Festival, the couple appeared unhappy. When asked if Madonna and Ritchie are breaking up or even just having problems, Madonna’s rep Liz Rosenberg—who only recently insisted the couple were still happily married—told PEOPLE, “No comment.”
On July 8 1985, Madonna was featured on the cover of People magazine with the caption: “Can Madonna get Sean to the alter?”
On March 6 1989, Madonna was featured on the cover of People magazine, as part of an anniversary celebration (15 years) issue.