In the early 90s, Madonna and Rosie O'Donnell seemed to come from two completely different worlds. Madonna was a superstar who was at the top of her game. She was touring the world with her successful "Blond Ambition World Tour" and had a huge hit with "Vogue."
O'Donnell was working the stand-up comedy circuit and started acting. This was way before she would get her own talk show or co-host The View. Her film debut came in 1991 when Penny Marshall cast her in A League Of Their Own. It was on the set of this film, however, that Madonna and O'Donnell's world would collide.
As it turns out, the two became friends and found that they shared a lot in common. Their friendship has remained so strong, the two are still in touch today.
Madonna And Rosie Met While Working Together On 'A League Of Their Own'
In 1991, Madonna was promoting her documentary Truth or Dare, which chronicled her 1990 "Blond Ambition World Tour." During promotion for the film, Madonna said that she wanted to delve deeper into acting.
Director Penny Marshall heard Madonna wanted to focus on acting, so she met with her to discuss A League of Their Own. Marshall spoke with Madonna about the role of Mae Mordabito, one of the Rockford Peaches.
The role introduced Madonna to O'Donnell, who played Mae's friend Doris. O'Donnell has since spoken about how nervous she was to meet Madonna.
"For 30-something years. I didn’t have any idea that I would be meeting her," O'Donnell told The Hollywood Reporter. "I was in baseball rehearsals for A League of Their Own. And Penny Marshall called me into the office and said (Penny Marshall voice), 'Madonna’s going to come to audition. If she likes you, and she likes me, maybe she’ll do the movie. Don’t be nervous.' I’m like, 'Don’t be nervous? What do you say to her? How do you connect to her?'"
According to O'Donnell, the two bonded over their shared grief of losing their mothers when they were very young.
"I told Madonna my mom died when I was 10, and I’m named after my mom, and so on her gravestone is my name as well."
The two became close friends in real life and have remained friends to this day.
"We formed a sister thing in a real way where we stay in each other’s lives and touch base," O'Donnell said. "She sends gifts to my kids on their birthdays, and my kids show all their friends: 'This is a gift card from Madonna!'"
"It's been a really, really, really grueling shoot, but I have learned a lot and I've made some really good friends," Madonna said at the time. "I think probably friends for life, a couple of the girls."
Rosie Defends Madonna After Her Provocative 'Letterman' Appearance Causes Controversy
In 1992, Madonna released her "Erotica" album and "Sex" book. The following year, her film Body of Evidence was released. The sexuality of all three projects proved to be too much for the public, who heavily criticized Madonna as a result. The singer experienced a level of backlash that had fans worried about the future of her career.
In 1994, Madonna appeared on the Late Show with David Letterman. Her appearance marked her second time speaking to Letterman, but her first appearance by herself.
Madonna called out Letterman for his constant jokes at her expense on his show. She even dropped the "f" bomb 13 times.
Madonna also made various innuendos. To top it all off, Madonna protested every time Letterman tried to go to commercial. There were even audience members who booed her and yelled at her to get off the stage.
Her appearance caused another wave of backlash in the press. In an interview with O'Donnell, the comedian said that she was told by Madonna that the producers encouraged her to swear during the interview.
"The people at Letterman had encouraged her to do that," O'Donnell told VH1. "That was not Madonna's idea. Regardless of whether or not they're going to admit it now, that's the truth."
O'Donnell even said she called Madonna the following day to confront her about the appearance.
"When I called her the next day, I'm like, 'What are you doing?' And she said, 'They told me to do it and they thought it would be funny and that they were going to beep it and that it was going to be funny.'"
Rosie Shared An Update With Fans After Madonna Was Hospitalized With A Bacterial Infection
In February 2023, Madonna introduced Sam Smith and Kim Petras' performance of their hit "Unholy" at the Grammy Awards. After she left the stage, she was trending online with many users commenting on her physical appearance. Many of the comments weren't very kind.
O'Donnell defended Madonna once again and told Page Six that she believed her friend was strong enough to handle the hate.
"You know, Madonna is one of the most famous women in the world and has been my entire lifetime," O'Donnell said. "And she would get vitriol at her at the height of her fame. I remember we were doing A League of Their Own and she had brown hair and we would be in an elevator and grown men, you know, would say to her, ‘I like you better as a blond.' And she would look at them and go, ‘You know, f–k you.’ And I thought, good for her, man, good for you."
According to O'Donnell, Madonna has "never had a problem standing up for herself."
"She knows who she is, what she wants, what she wants to look like, what she wants to wear, what she wants to say," she said. "And I think she’s strong enough to weather whatever complaints people have about her now and for always."
Later that year, Madonna was hospitalized in June with a bacterial infection. After being released from the hospital, O'Donnell shared an update with fans on the singer's condition.
"She's good," O'Donnell wrote on Instagram. "She is recovering at home. She is very strong in general."
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