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.
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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.”