Why Madonna May Be The Coolest Person Ever (Madonna 40th Anniversary Special)

How can one not be in awe of Madonna? Her massive global success for more than 40 years is backed by a keen intellect, deep cultural knowledge, immersion in myriad artistic expressions from highbrow jet-set and fabulous to lowbrow technicolor street. She’s fearless, transparent and candid; a strident feminist, wildly inclusive, sexually liberated and philanthropic AF. Madonna has a tireless work ethic, is incredibly organized and pushes herself to extremes. She is a dedicated collaborator giving others the space to create and thrive. When all these swirling qualities are combined it adds up to a preternatural cool.

Think about these real-life Madonna tidbits: Martha Graham gave her the name “Madame X” for her wild way of dressing. She starred in David Mamet’s “Speed The Plow” with Ron Silver and Joe Mantegna. She performed “Dress You Up” at Keith Haring’s birthday party at NYC’s house music temple the Paradise Garage. Macy’s held a Madonna lookalike contest with Andy Warhol as judge. He came to her wedding. So did Cher. Her 1987 “Who’s That Girl Tour” stop at MSG raised $400,000 for the American Foundation for AIDS Research. With her first big paycheck, she bought paintings by Léger and Frida Kahlo. She dated the brilliant Jean-Michel Basquiat. Her 2001 “Downed World Tour” title is based on J. G. Ballard’s crazily prescient 1962 novel “The Drowned World.” At Live Aid in 1985, she sang The Beatles’ “Revolution” with the Thompson Twins and Chic’s Nile Rodgers, who produced her second album. The Beastie Boys, with DJ Double R (Rick Rubin), opened her first tour. She starred in the George Harrison-produced film “Shanghai Surprise.” She covered songs by Elliott Smith, Cesária Évora and Vic Chesnutt. And that’s just a minuscule sliver of her stunning career.

“When I started out, I was sort of like a student, maybe like a little brother that didn’t have any money. I’d never seen the world. I had not traveled, I had not been to museums, I hadn’t seen art shows,” says Madonna’s manager Guy Oseary when describing how their relationship’s evolved over decades. “She held my hand through that and really helped me see things that were all new to me back then.”

Clues to Madonna’s voracious cultural appetite and intense drive can be found in her bio. She tragically lost her mother at 5 years old, some of her five siblings were artistically inclined and she was exposed at a young age to Catholic iconography. Her focus, discipline and love of dance was a pathway up, out and far beyond Michigan.

Christopher Flynn, her mentor and dance teacher while she was in high school, turned her on to art, culture and Detroit’s gay nightlife at a club called Menjo’s. “He was the first person who told me that I was beautiful or that I had something to offer the world, and he encouraged me to believe in my dreams, to go to New York,” Madonna told Gus Van Sant in Interview magazine.

Madonna moved to NYC in the early-’80s to study dance with Alvin Ailey and soaked up a universe of cultural riches. She donned dance slippers by day and Dr. Martens by night, playing in punk bands that gigged at CBGBs and Max’s Kansas City while she owned the dancefloors of legendary venues Danceteria, The Mudd Club and Paradise Garage. For a time, she lived in the Music Building, giving her entrée to the biz where she found other musicians, management and producers.

Former Village Voice columnist Michal Musto recalled sharing a bill with Madonna’s band at a venue called Chase Park when he played in a Motown cover band called The Must. “I didn’t find my experience with her all that pleasant,” Musto said by email, “but I later realized that she had the self-possession that may have been needed for her stardom. She was already acting as if she was the superstar she was destined to be, with a confidence that was astounding.

“After the gig, I started hearing a lot about her hanging out in the East Village and in the clubs. She was obviously giving out a lot of creative energy while at the same time sucking in the artistic spark in the air at that time, as well as the DIY hoist-yourself-by-your-own-petard attitude that artists relied on for survival and ultimately success. She was quite visible at clubs like Danceteria and all through the East Village and it was definitely a crucial moment in her formation.”

“She is a force, a musical force, a cultural force, a political force, at the vanguard and a role model for so many female artists,” said her longtime promoter Arthur Fogel. “She takes so many risks in her career and is upfront and doesn’t shy away from a lot of the things…With [‘The Celebration Tour’] you realize her catalog of hits, apart from everything else, the actual hit after hit after hit, she’s been such a strong musical force in the pop world for so long — it’s pretty awe-inspiring.”

And that’s coming from someone who worked with David Bowie, another legendary artist of many who inspired and influenced Madonna.