Rosie O’Donnell Says Seeing What Superstardom Was Like for Bestie Madonna in the ’90s Was a 'Cautionary Tale'

Mar. 15, 2025

Rosie O’Donnell and Madonna in 1992.Photo:Sonia Moskowitz/Getty

Sonia Moskowitz/Getty

Becoming besties withMadonnain the ’90s changed the wayRosie O’Donnellthought about fame.

On the most recent episode ofDavid Duchovny’s podcastFail Better,the comedian, 62, looked back on her early brush with superstardom when she and the Queen of Pop became close during the filming ofA League of Their Own.

In the beloved 1992 film, Madonna and O’Donnell starred as All-American Girls Professional Baseball League players “All the Way Mae” Mordabito and Doris Murphy, respectively. Like their characters, the two performers became friends on set and have remained close ever since.

Madonna and Rosie O’Donnell in ‘A League of Their Own’ in 1992.Columbia Pictures/ Courtesy: Everett Collection

Columbia Pictures/ Courtesy: Everett Collection

“To be cast in a movie opposite the most famous woman in the world as the best friend — right, me and Madonna? That was like a life-altering casting session for me because it changed my whole world,” O’Donnell told Duchovny. “That kind of fame is once a generation, you know? That kind of Elvis, the Beatles, Madonna. And to be that close to it for so long and be able to get an opinion of what it does to the human being through being that close to, you know, Madonna.”

Seeing first-hand how the public interacted with the “Material Girl” singer, O’Donnell explained, was eye-opening.

“I thought that I wanted [that kind of fame],” she said, “but I thought, ‘Look at how much it takes away from her.’ We were in a elevator, and people would say to her face, ‘I like you better with blonde hair,’ because inLeagueshe had dyed her hair brown. And she’d be like, ‘Yeah, f— you.’ You know?”

Rosie O’Donnell and Madonna in 1993.Robin Platzer/Getty

Robin Platzer/Getty

“I realized how many people felt that they had the right to say whatever they wanted to her, that she had lost her humanity in the eyes of the public from being too famous,” O’Donnell continued. “And it was like a cautionary tale in a way. Not that I ever thought I would achieve that level of fame, but that any level of fame could be as toxic and demanding.”

As Duchovny noted, O’Donnell would ultimately become a household name, similar to Madonna, largely via her Emmy-winning daytime talk show,The Rosie O’Donnell Show, which aired from 1996 to 2002, and later as a co-host onThe View.

Madonna and O’Donnell have remained close friends over the years. In 2016, the pop star came to the comedian’s defense after Donald Trump made a derogatory remark about her during a presidential debate. “Mess with my girl Rosie and you’re messing with me!!!” Madonna wrote in an Instagram post at the time.

Rosie O’Donnell and Madonna in 2003.Bruce Glikas/FilmMagic

Bruce Glikas/FilmMagic

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Back in March, O’Donnell posted athrowback photoof herself and Madonna attending an Oscars party together prior to the release ofA League of Their Own— a memorable eventthe actress described to PEOPLE in 2021 as “so wild.”

source: people.com