Prince, Madonna, and Michael Jackson were all born within three months of each other.
Three Midwestern babies born in 1958 grew up to change the course of pop music and culture forever. Prince Rogers Nelson was born on June 7 in Minneapolis, Minnesota; Madonna Louise Ciccone was born on August 16 in Bay City, Michigan; and Michael Joseph Jackson was born on August 29 in Gary, Indiana. Each of the future genre-busting superstars was welcomed into a big family: Eventually, Prince had eight siblings, Madonna had seven, and Jackson had 10. Jackson was the first to begin his performing career, at age 5. Six years later, he made his television debut as the youngest member of the Jackson Five when the group sang “It’s Your Thing” at the Miss Black America Pageant. Prince debuted at 21 on American Bandstand, singing "I Wanna Be Your Lover" and "Why You Wanna Treat Me So Bad?”; Madonna made one of her earliest TV appearances on the same show four years later, performing “Holiday,” and telling Dick Clark of her wish to “rule the world.”
In addition to exhilarating music, era-defining music videos, and various business ventures, all three made films. Precocious Jackson appeared in the first movie of the group, 1978’s The Wiz, a straight-from-Broadway reimagining of The Wizard of Oz featuring an all-Black cast (Jackson played the Scarecrow). In 1985 — the year Prince and Madonna briefly dated — Prince won an Oscar for Best Music, Original Song Score for his first film, the semi-autobiographical Purple Rain. Meanwhile, shortly after Madonna (in a Marilyn Monroe-inspired look) took Jackson as her plus-one to the 1991 Academy Awards, she shot A League of Their Own, a tribute to the all-female baseball teams that entertained fans during World War II. (The so-called Queen of Reinvention has also appeared in dozens of other films over the years.)
Costume designer Penny Rose dressed Madonna in 85 outfits when she portrayed Argentinian actress, activist, and First Lady Eva Perón in the 1996 film Evita. Those clothes were accessorized with 45 pairs of shoes, 56 pairs of earrings, and 39 hats. In a savvy branding tie-in, Bergdorf Goodman began selling Perón-inspired hairpieces, and Madonna — pregnant with her first child, Lourdes Leon, during filming — even channeled her alter-ego for the cover of Vogue. Madonna won a Golden Globe for her performance in director Alan Parker’s musical biopic (an adaptation of the Andrew Lloyd Webber musical), and Rose received a BAFTA nomination for her costumes.
