Madonna's obsession with Wallis Simpson revealed as the Queen of Pop shares heartbreaking reason she feels connected to the late royal

Madonna's obsession with Wallis Simpson shows her deepest vulnerabilities as well as a shared passion for the finer things in life

Wallis, Duchess of Windsor (1896-1986) outside Goverment House in Nassau, the Bahamas, circa 1942. The Duke of Windsor served as Governor of the Bahamas from 1940 to 1945 AND Madonna attends the Costume Institute Gala for the "PUNK: Chaos to Couture" exhibition at the Metropolitan Museum of Art on May 6, 2013 in New York City.
(Image credit: Ivan Dmitri/Michael Ochs Archives/Getty Images AND Jennifer Graylock/FilmMagic/Getty Images)

Madonna's obsession with Wallis Simpson is revealed in throwback interviews that give a heartbreaking insight into the lived experience both women shared. 

Madonna at the Tom Ford Spring 2023 Ready-to Wear show.

(Image credit: Nina Westervelt/WWD via Getty Images)

It's easy to look at throwbacks like Wallis Simpson’s bizarrely luxurious menu for a special event and her controversial marriage to Prince Edward and - whether you like her or not - believe that she didn't give two hoots about what anybody thought.

Some may say the same about the Material Girl singer, who's carved her own creative path throughout her decades-long career - seemingly not giving a damn and being judged harshly in the process.

Madonna feels so connected to Wallis that she even made a film that juxtaposed the affair between King Edward VIII and the American divorcée with a contemporary romance between a married woman and a Russian security guard.

Speaking to Reuters Television back in 2012, Madonna gave an insight into why she feels so connected to the Duchess of Windsor.

“I could understand a lot of aspects of Wallis Simpson’s life, having people...view you from the outside, make judgments about you, have opinions about you, write things about you that are untrue," she said, "and not feel like you are able to defend yourself, that sometimes kind of makes you feel helpless.” 

The Duchess of Windsor, Wallis Simpson, at her greenhouse in Bois de Boulogne near Paris, France 1974.

(Image credit: Wolfgang Kuhn/United Archives via Getty Images)

Although the singer is far from a shrinking violet, the extent of the constant barrage of criticism she receives would be hard on anyone - just like it must have been on the late Duchess.

"Obviously I can relate to her life on certain levels," admitted Madonna. "I think that a lot of people who are public figures have the same experience."

Duke & Duchess Of Windsor At Their Temporary Home - Ashdown Forest, Sussex.

(Image credit: © Hulton-Deutsch Collection/CORBIS/Corbis via Getty Images)

After Madonna married British director Guy Ritchie, she packed her bags and moved to the UK. She was dubbed 'Madge' and seemingly took to living a quieter life, for a time. 

It was during this time that she was stunned by the outrage provoked by Wallis' name, she told Harper's Bazaar, and in writing the movie that she really noticed the connections between herself and the Duchess. 

"I think my behavior and my lifestyle threaten a lot of social norms, like the movie does," she said. "I think there are a lot of parallels and connections." 

Guy Ritchie And Madonna Arrive At The World Premiere Of 'Rocknrolla' At The Odeon Cinema, Leicester Square.

(Image credit: Antony Jones/UK Press via Getty Images)

Their connections may also be more style based as it's rumored that when a selection of Wallis' jewelry went to auction at world-famous auction house Sotheby's, Madonna tried a few pieces on.

She's said to have taken a particular interest, per the Guardian, in the Cartier panther bracelet - which sold for a record-breaking $5.6M/£4.5M.

A Cartier onyx and diamond panther bracelet from 1952 estimated at £1,000,000 - £1,500,00 is displayed at Sotheby's on September 23, 2010 in London, England. The Jewels of the Duchess of Windsor collection will be auctioned in London on November 30, 2010. The collection, originally auctioned in 1983, comprises 20 pieces owned by Wallis Simpson, The Duchess of Windsor.

(Image credit: Peter Macdiarmid/Getty Images)

Sotheby's description of the piece detailed its, "articulated body designed to encircle the wrist and to assume a stalking attitude, pave-set with brilliant and single-cut diamonds and caliber-cut onyx, the eyes each set with a marquise-shaped emerald."

Though they couldn't possibly confirm who bagged the bracelet, many reported that the Queen of Pop made the purchase after all.

Aoife Hanna
Junior News Editor

Aoife is an Irish journalist and writer with a background in creative writing, comedy, and TV production.

Formerly woman&home's junior news editor and a contributing writer at Bustle, her words can be found in the Metro, Huffpost, Delicious, Imperica and EVOKE.

Her poetry features in the Queer Life, Queer Love anthology.

Outside of work you might bump into her at a garden center, charity shop, yoga studio, lifting heavy weights, or (most likely) supping/eating some sort of delicious drink/meal.