Are Madonna And Rosie O'Donnell Still Friends?

Madonna and Rosie O'Donnell don't make for the most obvious of BFFs. However, their friendship spans back decades. The two became close after Madonna scored a role in "A League of Their Own." They both starred in the 1992 baseball flick alongside Geena Davis, Lori Petty, Tom Hanks, and Megan Cavanagh, per IMDb.

Despite Madonna's formidable diva reputation, O'Donnell wasn't scared of teasing the pop icon. And, far from being insulted, Madonna actually loved her bravado and ballsy attitude, revelling in their mock confrontations. "Rosie would sing all of 'Holiday,' and Madonna would get mad at her and say, 'Don't ever sing one of my songs again,'" co-star Cavanagh told Entertainment Weekly in 1992 (via E! News). "And the next day, [O'Donnell would] come out and sing 'Vogue.' It was so fun to watch her do that."

The actor's abrasive attitude has lost her many pals over the years. It was one of the reasons why O'Donnell left "The View" in 2007 after she got into a truly epic daytime TV fight with right-wing co-host Elisabeth Hasselbeck over then-president George W. Bush. Following her exit, O'Donnell shared in a video (via Page Six) that Hasselbeck tried calling her, but she had no intention of ever talking to her again. O'Donnell returned to the show in 2017. Still, she only lasted one season before falling out with Whoopi Goldberg and several staffers, according to Variety. So, are Madonna and Rosie O'Donnell still friends, or did another relationship bite the dust?

Rosie O'Donnell was front and center at Chifundo Mercy James' 15th birthday party. Madonna's youngest daughter celebrated by showing off her steezy flips and front-sides at a local skatepark along with her brother David Banda, twin siblings Stelle and Estere Ciccone, and friends. Mercy's mom didn't bust out with boardslides or blunts in the bowl. Instead, she stood on the sidelines with O'Donnell, both dressed in their hippest urban hoodies and shades, filming the maneuvers.

"SkatePark extravaganza for Mercy James birthday," Madonna captioned the clip on Instagram. Rosie also posted a pic of the crew. "happy birthday Mercy James #love," she wrote. Meanwhile, People reported that when Madonna kicked off her "Madame X" tour, O'Donnell was right there, even making a guest appearance at one point. When Madonna auctioned a selfie of herself, O'Donnell strode onstage and handed over a wad of cash for the photo. She also cozied up to her bestie in an after-show photo taken by Madonna's manager Guy Oseary along with Debi Mazar, Spike Lee, and Anderson Cooper.

Rosie's daughter Vivienne was as shocked as everyone else to learn her mom was BFFs with Madonna. In fact, she admitted to not even recognizing "this beautiful lady, Mo," who always turned up at family parties and brought over her brood for playdates. "I never had any idea who the f**k she was," Vivienne admitted in a TikTok video (via Access Hollywood).

Madonna's a staunch defender of Rosie O'Donnell. She has the comedian's back, and if anybody attacks her, they have the singer to answer to. O'Donnell's feud with Donald Trump is legendary. "[He] left the first wife — had an affair. [He] had kids both times, but he's the moral compass for 20-year-olds in America. Donald, sit and spin, my friend," she said during an episode of "The View" in 2007 (via People). Trump hit back hard, slamming O'Donnell repeatedly, "Rosie's a loser. A real loser," he told the publication in response. "I look forward to taking lots of money from my nice fat little Rosie."

Madonna told "Today" (via CTV News) that despite being on vacay "in the middle of the Indian Ocean," she messaged O'Donnell as soon as she heard about Trump's rant. "She's a stand-up comic. I think all stand-up comics talk about provocative things," Madonna said. "I have a feeling that if every stand-up comic was penalized for saying politically incorrect things or provocative things, I think they'd all be hung in the public square," she concluded.

Meanwhile, O'Donnell's only issue with her BFF is her late-night dinner times. "Madonna's pretty good [right now]. I'm gonna see her this weekend," she told Andy Cohen in 2020. O'Donnell explained that Madonna's a great cook, but she never gets the chance to sample her food. "They eat very late," she said. "Like 10 o'clock! She's like, 'Why can't you ever come to dinner?' Because I was sleeping then!"