Madonna

An icon of unabashed ambition and sexual magnetism, Madonna has been making headlines since the early MTV Age for her musical talents and much more. Cosmo caught up with the Material Girl in July 1987 to talk about her rising hopes for a career in Hollywood and her then-marriage to bad boy heartthrob Sean Penn. Endearingly frank and forever flirting with the wild side, some things never change: 36 years later, she remains the star we fell for then. -

Having been rendered somewhat cautious by Shanghai Surprise, Madonna didn’t leap to say yes when James Foley (who had directed Sean in At Close Range) brought her the script that subsequently became the movie Who’s That Girl—a romantic comedy in which she plays a character much like the one in Desperately Seeking Susan. “I said, ‘I like it, but it needs a lot of work.’ We went through several writers and several revisions of the script until it was just what we wanted.” Director Foley is convinced Madonna was born to be a movie star. “The form is big enough, she was made for widescreen Technicolor. And she is precociously talented. Every time I would say ‘Action!’ what she would do would make me giggle with excitement. She’s very instinctual, what comes out is unencumbered by analysis. Who’s That Girl was for me technically difficult, we shot on the streets of New York and L.A., but she helped. Everyone on a crew observes the tone the star sets, and she emanated such a sense of ease and dignity, it filtered clear down to the caterer. She’s curious as hell too—about lights, scripts, people’s names.”