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 is revealed in throwback interviews that give a heartbreaking insight into the lived experience both women shared. 

• Madonna's obsession with Wallis Simpson was owing to a very particular kinship she felt with the late royal.
• The Queen of Pop wrote and directed a film, W.E, about Wallis and was said to be interested in a famous piece of jewelry belonging to the late Duchess when it went to auction.
• In other royal news, The sign Princess Anne and Princess Charlotte are super alike - and we're not talking about their appearance.

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.” 

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."

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." 

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.

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.