During Her Interview With Howard Stern, Madonna Admitted She Asked Warren Beatty About His Exes While They Dated

Summary

• Warren Beatty inspired Madonna's song "Vogue" while dating her after they worked on Dick Tracy together.
• Madonna didn't mind Beatty's famous exes and even asked about them, valuing them as inspirations.
• Madonna's brother regretted writing about her relationship with Beatty, suggesting they should have married.

In 1989, Madonna divorced her first husband, Sean Penn. Shortly after the divorce, Madonna began working on the film Dick Tracy. The project would see her working alongside the legendary Warren Beatty.

The project would also lead to the two developing a romance, which would dominate headlines at the time.

While Madonna's relationship with Beatty didn't last, it is still remembered all these years later. During a 2015 interview with Howard Stern, Madonna was asked about her experience dating Beatty. Madonna's revelation about her time with Beatty shocked the host.

Madonna Told Howard Stern She Asked Warren About His Previous Famous Girlfriends

Madonna appeared on The Howard Stern Show in 2015 to promote her album "Rebel Heart." During their conversation, Stern asked Madonna about writing her hit "Vogue."

Madonna then explained how the song came to be, revealing it was prompted by a request from her then-boyfriend Warren Beatty. The two starred together in the live-action film version of the comic book series "Dick Tracy." Beatty asked Madonna to write a song for the film.

"I had seen people voguing. Warren asked me to write a song for Dick Tracy and I was thinking about all of the movie stars. Warren grew up in that era and he dated all of Hollywood, basically," Madonna told Stern.

Stern then asked Madonna if she was freaked out by dating a man who has "dated everyone." Madonna then said that she didn't mind it. In fact, she revealed to Stern that she even inquired about his famous ex-girlfriends.

"I would say things like, 'What was Julie Christie like?' 'What was Natalie Wood like?' He was with such amazing women," Madonna admitted.

Stern was shocked at Madonna's revelation. "You would say that to him?" he asked.

Stern went on, "I think most women don't want to know. It just feels kinda weird."

"But I looked up to them and admired them," Madonna explained.

Stern then asked Madonna if it was "like bragging to your girlfriend," to which she replied, "No, I asked the question. He didn't bring it up. I asked the question. I wanted him to tell me."

It then became clear that Stern mistakenly believed Madonna was asking Beatty what his famous exes were like in bed. However, Madonna was quick to clear that up.

"I wanted to know what they were like as people, not lovers," she said.

Madonna Started Dating Warren Beatty After Her Divorce From Sean Penn

Madonna and Beatty began dating following her divorce from actor Sean Penn. Penn and Madonna met on the set of her "Material Girl" music video. The two would be married eight months later on August 16, Madonna's 27th birthday, Penn turned 25 the next day.

Madonna and Penn's wedding day was filled with chaos and turmoil. For starters, paparazzi found out about the date and location after the information leaked out. Helicopters filled with cameras swarmed and hovered over the outdoor ceremony. It was said that guests could barely hear the exchange of vows.

Penn carved out an explicit insult to photographers in the sand and Madonna flipped them off. It was even rumored that Penn fired a gun at photographers during the event.

Penn was starting to become known for his violent temper and his run-ins with paparazzi got him into lots of legal trouble.

Madonna first filed for divorce in December 1987, but withdrew the filing two weeks later. In January 1989, Madonna filed again. There were also rumors that Madonna withdrew an assault complaint against Penn following an alleged incident at their home in Malibu, California.

These rumors have stayed with Penn through the years. In 2015, Penn filed a $10 million defamation suit against Lee Daniels after Daniels suggested the rumors about Penn were true. Madonna wrote a letter to the court in which she denied the allegations. Penn later dropped the lawsuit after Daniels retracted his statement and issued an apology.

In Madonna's 1991 tour documentary Truth or Dare, her relationship with Beatty was explored as he met her at several stops on her world tour. However, he was clearly uncomfortable with the presence of the cameras, uttering the now-famous line, "She doesn't want to live off-camera."

Later in the film, Madonna is asked who the greatest love of her life had been. With a slight voice crack, Madonna replied, "Sean."

Madonna's Brother Had Some Thoughts About Her Relationship With Warren Beatty

Madonna appeared on The Jonathan Ross Show in 2015 where she performed and sat down for an interview. During the chat, Ross mentioned the book "Life With My Sister Madonna," written by Madonna's brother, Christopher Ciccone.

Madonna said that she was "really hurt" by the book and "there were many years of silence" between her and Ciccone. However, she also revealed that the two reconciled and that she believes "he feels bad that he did it."

Ross then said that in the book, Ciccone mentioned Madonna's relationship with Beatty. According to Ross, Ciccone wrote that he believed Beatty was right for Madonna and she should've married him. Madonna responded by saying that while Beatty was ready, she wasn't due to her recent divorce.

"I was in 'going crazy mode,'" Madonna said.

Ciccone also spoke negatively about Madonna's second husband, film director Guy Ritchie. Ciccone accused Ritchie of being homophobic, which the director denied. Madonna and Ritchie married in 2000 and filed for divorce in 2008, the same year Ciccone's book was released.

During their interview, Madonna told Ross that her marriage to Ritchie ended because of timing. That same year, she opened up to The Sun and revealed even more.

"I did sometimes find myself in a state of conflict," she said. "There were times when I wanted to express myself as an artist in ways that I don't think my ex-husband was comfortable with."

Many noticed that Madonna's image and music became much more provocative in the wake of the divorce.

"There were times I felt incarcerated," she added. "I wasn't really allowed to be myself."