Madonna Confounding Expectations

Madonna Confounding Expectations  by Rosemary McKittrick

Photo courtesy of Julien's Auctions.

“It’s hard not to love the way Madonna confounds expectations: She’s survived and thrived in an industry that reviles both female aging and sexuality that isn’t male-controlled,” said writer Jessica Valenti. 

That’s one way of looking at it. Whether you admire or reject the pop icon Madonna stirs people up in the same way Marilyn Monroe did. So many different feelings around the Material Girl. Some contrary to others.

Madonna doesn’t make apologies for messy hair, sassy behavior, blonde Afro wigs, lacy gloves, burning crosses, and pointy-coned bras. On one level it all seems like a game of pretend. Or is it?

I hope that I inspire women to believe in themselves, no matter where they come from; no matter what education they have; what particular background they originate from.
— Madonna

What’s unmistakable is Madonna overcame the Beatles on the list of all-time consecutive top-five U.S. singles, 16 in a row. She was also named the world’s top-earning female entertainer.  She is no one-hit wonder

Madonna remains a strong, ambitious woman who doesn’t apologize for the way she shows up in life.

“Don’t tell me I can’t be sexual and intelligent at the same time,” she said. She invites females to rethink sexuality.

The Material Girl first showed up in New York City with about $35 dollars in her pocket and eventually moved into an apartment in the East Village. Like other struggling artists she waited tables, worked as a figure model, and acted in low budget movies. She also danced backup for local bands which allowed her to showcase her talents and rub shoulders with musicians in the industry,

If anything Madonna as singer, performer, dancer, actress, songwriter, mom, and businesswoman--is a lesson in tenacity. Pretty remarkable for a kid born in 1958 as Madonna Louise Veronica Ciccone and growing up in Bay City, Michigan. 

Madonna has been on the music scene now for over three decades and she created herself and her persona from the ground up. 

“One of the things that helps me tell a story through music is to create a character. I have to have a muse, whether it's Frida Kahlo, Martha Graham, Marlene Dietrich, or Pippi Longstocking,” Madonna said.

With roles in films like Desperately Seeking SusanDick Tracy, A League of Their Own and Evita Madonna added acting to her list of accomplishments.

Like her or not, you got to hand it to the woman. She’s come along way and shows no signs of backing off yet. 

“I hope that I inspire women to believe in themselves, no matter where they come from; no matter what education they have; what particular background they originate from,” she said.

Madonna says it has never been her nature to kickback and from her career path and choices that appears to be true.

On May 20, Julien’s Auctions featured a selection of Madonna items in its Music Icons sale.


Photograph; black-and-white, taken by Herb Ritts, 1990; 14 ¼ inches by 11 ¼ inches;  $576.

Signed Program; Who’s That Girl; 1987; signed by Madonna and her crew; inscriptions to Pilar DeMann, daughter of Madonna’s manager; 14 inches by 11 inches;  $1,024.

Signed Hat; black felt with chin strap; made by Golden Gate Hat Company; believed to have been worn for Madonna’s Blond Ambition Tour; from Dick Clark collection;  $1,920.

Worn Shoe; mid-calf right-sided black boot with rhinestone accents; worn by Madonna in her role as Susan in Desperately Seeking Susan; 1985; $5,120.

MTV Video Music Award; Moon-Man trophy; presented to Freddy DeMann for Best Art Direction in a video for Madonna’s Rain; 1993; 12 inches high; $11,250.     


Rosemary McKittrick is a storyteller.  For 26 years she has brought the world of collecting to life in her column.  Her website is a mother lode of information about art, antiques and collectibles.  Rosemary received her education in the trenches working as a professional appraiser.

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