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O’Donnell and Madonna previously starred together in the 1992 movie classic “A League of Their Own.”
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Rosie O’Donnell has opened up about her friendship with Madonna — including observing her “very tight ship” parenting style.
The comedian and actress revealed details about play dates the pair’s children used to have.
O’Donnell and Madonna previously starred together in the 1992 movie classic A League of Their Own.
Rosie O’Donnell has revealed that longtime friend and A League of Their Own costar Madonna (unsurprisingly) runs a “very tight ship” as a parent.
Ahead of her upcoming guest-hosting stint filling in for the titular host on Jimmy Kimmel Live, the 64-year-old comedian and actress reflected on her decades-long friendship with the Queen of Pop — including insights into Madonna’s parenting style.
“We text, and I go to her house, and we talk about the kids,” O’Donnell recently told Entertainment Weekly‘s sister publication, PEOPLE. “She ran a very tight ship. I had a very not tight ship.”
Madonna, 67, has six children — including Rocco Ritchie and Lourdes Leon, who appears as a guest vocalist on her new Confessions II album song “The Test” — while O’Donnell has five, and the former View cohost said they’d let their families mix during the kids’ formative years.
“Her kids Lola and Rocco would come over for a playdate, and I’d give them an ice pop, and turn on the cartoons,” O’Donnell said.
She also explained how she and Madonna bonded over the deaths of their own mothers, a subject that has long worked its way into Madonna’s musical output (particularly on songs like 2003’s “Mother and Father” and 2026’s “Betrayal”).
O’Donnell said she’d “never met another woman whose mother died and they’re named after the mother,” and recounted the haunting reality of going to the “grave site” and seeing “your name on the tombstone.”
She continued, “When we met, it was the first thing I said: ‘My mom died when I was young, and I was named after her too.’ It’s like we became sisters at that moment.”
O’Donnell also opened up to the outlet about her relationship with her own children, including Chelsea, who was recently sentenced to prison after her probation was revoked in October 2025.
“She’s sober, and that’s changed everything. She ran away at 17 to her birth mother and to a very drug-addled community in Wisconsin,” O’Donnell said. “I recently visited her in prison, which was overwhelmingly emotional, but I saw the kid that I used to know. She calls every day, and we talk.”
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The star additionally spoke about raising a child with autism.
“Clay’s vulnerability has forced me to be more connected and attached and for us to be close in a way that I hadn’t been with my other kids. Autism is so miraculously curious,” the pop culture icon noted. “Clay understands very big concepts for a kid who’s only 13. They said to me once, ‘Do you realize that Cleopatra lived closer to the invention of the iPhone than she did to the completion of the Pyramids of Giza? Common knowledge.’ Hence the name of my show. I went into the bathroom and googled that, and it’s true.”
O’Donnell’s guest-hosting gig on Jimmy Kimmel Live begins in August on ABC.
Read the original article on Entertainment Weekly
