Rosie O’Donnell reveals how she and Madonna instantly became 'sisters'

Rosie O’Donnell and Madonna's friendship began after they met on the set of the 1992 sports comedy film 'A League of Their Own'
Rosie O'Donnell opened up about her decades-old friendship with Madonna during an interview with PEOPLE (Sonia Moskowitz/Getty Images)
Rosie O'Donnell opened up about her decades-old friendship with Madonna during an interview with PEOPLE (Sonia Moskowitz/Getty Images)

LOS ANGELES, CALIFORNIA: Rosie O’Donnell has shared about her sisterly bond with Madonna in a new interview.

The comedian and the singer's friendship began after they met on the set of the 1992 sports comedy film 'A League of Their Own'. 

Rosie O’Donnell shares what made her and Madonna bond

While speaking with PEOPLE, O’Donnell recalled what exactly she told the "Queen of Pop," which immediately made them “sisters”.

Rosie O'Donnell and Madonna during Madonna and Rosie O'Donnell Backstage at
Madonna and Rosie O'Donnell at The Plymouth Theater in New York in 2003 (Bruce Glikas/FilmMagic)

“I had just seen ‘Truth or Dare’, and I had never met another woman whose mother died, and they're named after their mother, and then when you go to the gravesite, you see your name on the tombstone,” she told the publication.

The 64-year-old further shared, “The first thing I said was, ‘My mom died when I was young, and I was named after her too,’ and it was like we became sisters at that moment.”

Rosie O’Donnell's mother died when she was only 10 years old

O’Donnell was referring to Madonna’s 1991 documentary. Both were named after their late mothers. While the former talk show host lost her mother when she was 10, the record producer’s mother died when she was just five.

Madonna and Rosie O'Donnell at the Bergdorf Goodman in New York City, New York
Madonna and Rosie O'Donnell during 'Lotsa de Casha' by Madonna Book Launch Party at Bergdorf Goodman in New York on June 7, 2005 (Kevin Mazur/WireImage)

The actress further revealed that nowadays when she and Madonna meet, they “talk about the kids. We just hang out when she’s in New York.”

Rosie O’Donnell says Madonna has done 'one hell of a job' raising her children

O’Donnell also hailed the ‘Popular’ hitmaker’s parenting style. She said, “I have to say Madonna has done one hell of a job raising those children. She ran a very tight ship, and I had a very not tight ship.”

“Her kids, Lola and Rocco, would come over for a playdate when they were little, and as soon as she left, I would give them an ice pop and turn on the cartoons. They didn’t get to watch TV,” she shared.

The ‘Star Search’ star even praised Lola and Rocco as she added, “Those kids are concert pianists and artists and singers. She is pretty phenomenal. And a motherless daughter, even younger than I was when her mother died.” 

Lourdes Leon and Madonna attend the Saint Laurent Womenswear Spring/Summer 2026 show as part of Paris Fashion Week on September 29, 2025 in Paris, France. (Photo by Pascal Le Segretain/Getty Images)
Lourdes 'Lola' Leon and Madonna attend the Saint Laurent Womenswear Spring/Summer 2026 show as part of Paris Fashion Week on September 29, 2025, in Paris, France (Pascal Le Segretain/Getty Images)

Madonna is also the mother of four adopted children — David, Mercy, and twins Stella and Estere.

Rosie O’Donnell opens up about seeing daughter Chelsea in jail

Whereas O’Donnell has five children — Parker, Chelsea, Blake, Vivienne, and Clay. She shares her four oldest children with her first wife, Kelli Carpenter, and welcomed her youngest with her second wife, Michelle Rounds.

Rosie O'Donnell and Chelsea Belle O'Donnell pose at the
Rosie O'Donnell and Chelsea O'Donnell pose at the '2nd Annual Fran Drescher Cancer Schmancer Sunset Cabaret Cruise' on The SS Hornblower Infinity Cruise Ship on June 20, 2016, in New York City (Bruce Glikas/Bruce Glikas/FilmMagic)

O’Donnell even talked about her daughter Chelsea, who’s currently behind bars. “She’s sober, and that’s changed everything. She ran away at 17 to her birth mother and to a very dr*g-addled community in Wisconsin,” the comedian shared.

“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,” O’Donnell added.

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