In the 1980s and 1990s, Madonna was such a big star that people started comparing her to Marilyn Monroe. Madonna had the hit songs, of course—such as Like a Prayer and Vogue, to name a couple. But as the reigning sex symbol of the MTV generation, she had a a cultural influence that went beyond her album sales.
This collection of photos from the height of her fame shows her on stage but also highlights the company she kept. Here she is pictured with, among others, Warren Beatty (her costar in the movie Dick Tracy and also a one-time flame), Sean Penn (her husband from 1985 to 1989), Rosanna Arquette (her costar in the movie Desperately Seeking Susan), Jellybean Benitez (the DJ who produced Madonna’s early music) and actors Joe Mantegna and Ron Silver (her costars in the 1988 Broadway production of David Mamet’s Speed-the-Plow).
This collection also includes a photo of Madonna with Michael Jackson, the rare pop star who could meet her on equal footing. The two attended the 1991 Academy Awards together, which led to breathless speculation that they might actually be a couple. Madonna later told VH1 that their Oscar night date came about in a casual way: “Michael was like, ‘Well, who are you going to go with? I looked at him and said, ‘I don’t know. You want to go?’ And he said, ‘Yeah, that’d be great.’” While their relationship seems to have been mostly friendly and professional, Madonna did say that they kissed at one point, with her playing the initiator.
But even if the reality is that there wasn’t all that much to their relationship—they never made any music together either, despite apparently discussing the possibility—it’s not hard to see why the mere idea of their union gripped the imagination. A relationship could have led to an American version of a royal wedding. Thus does the photo of these two icons attending the Academy Awards remain the best-selling image of Madonna in the LIFE print store.
It is one of many wonderful photos of Madonna in the LIFE archives, and here is a sampling of some favorites. Especially when she was on stage, she could strike a pose like there was nothing to it.
Madonna and Michael Jackson (left) arrived at the Shrine Civic Auditorium for the 63rd Annual Academy Awards ceremony, March 25, 1991.
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Madonna performed at the MTV Video Music Awards at Radio City Hall in New York, 1984.
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Singer Madonna with record producer Jellybean Benitez at tge opening of the club Private Eyes, 1984.
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Madonna with Rosanna Arquette, the costar of her 1985 film “Desperately Seeking Susan.”
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Madonna with singer David Lee Roth in the mid 1980s.
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Madonna out for a run with a trainer, 1987.
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Madonna in concert, 1987.
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Madonna with actor Sean Penn, her husband from 1985 to 1989.
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Madonna in concert, 1987.
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Madonna in concert, 1987.
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Madonna with Ron Silver (left) and Joe Mantegna (right), her costars in the Broadway production of the David Mamet play Speed-the-Plow, 1988.
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Madonna in concert, 1988.
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Madonna performed in Los Angeles during her Blonde Ambition tour, 1990.
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Madonna in concert, 1990.
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Madonna with her boyfriend, model Tony Ward, at the premiere of the 1990 film Goodfellas at the Museum of Modern Art; Ward appeared in videos for the Madonna songs “Cherish” and “Justify My Love.”
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Madonna with Rosie O’Donnell, her costar in the 1992 movie A League of Their Own.
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Madonna performed at Madison Square Garden, 1993.
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Former flames Warren Beatty and Madonna at the nightspot Moomba for the premiere party of the 1997 motion picture Two Girls and a Guy.
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Bob Dylan and Madonna in the late 1990s.
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Madonna in concert, 1990.
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