How Childhood Tragedies Helped Bond Rosie O'Donnell And Madonna As Forever Friends

Comedian, author, actress, and television personality Rosie O'Donnell and world-famous pop icon Madonna may not seem like the most likely friends at first glance. However, the stars have actually been very close since the early 1990s when they first met while filming their 1992 sports comedy, "A League of Their Own." Ever since then, they've remained close and had each other's backs through good times and bad. 

Decades ago, when O'Donnell heard that she was going to meet Madonna for the movie, she was extremely intimidated. As it turns out, the multi-hyphenate had nothing to worry about; she and the singer quickly formed a deep connection because of their shared tragic past. Both women lost their mothers when they were young children (O'Donnell was 10 and Madonna was five), and their grief became the foundation of a long-lasting, beautiful friendship that provided them with comfort and a unique opportunity to heal.

Rosie O'Donnell opened up about her friendship with Madonna during a June 2023 interview with The Hollywood Reporter, sharing that until Madonna showed up to audition for "A League of Their Own," she never expected to meet the "Vogue" singer. "I was in baseball rehearsals for 'A League of Their Own,' the comedian recalled. "And Penny Marshall called me into the office and said (Penny Marshall voice), 'Madonna's going to come to audition. If she likes you, and she likes me, maybe she'll do the movie. Don't be nervous.'" At the time, O'Donnell was, of course, extremely nervous. She wasn't sure how she was going to connect with the pop star and didn't want to make a fool out of herself.

However, the two became fast friends when O'Donnell shared that her mother had died when she was 10 and that she's named after her. Madonna lost her own mother when she was just five, so they immediately connected. "We formed a sister thing in a real way where we stay in each other's lives and touch base," O'Donnell revealed of their relationship all these years later. Madonna even sends O'Donnell's kids birthday gifts. O'Donnell revealed, "My kids show all their friends: 'This is a gift card from Madonna!'"

When Donald Trump launched a media campaign against Rosie O'Donnell in the 2000s, Madonna was there to support her friend. The singer heard the news while she was on a remote island, and at the time, she called up O'Donnell to ask about what was going on. After the actress explained the messy situation, Madonna had her back. When asked about Trump and O'Donnell in interviews, she said, "I firmly support Rosie." O'Donnell admitted to The Hollywood Reporter that her friend's support came "at a very needed time."

In April 2023, O'Donnell stood up for Madonna when people on the internet bullied the singer about her appearance. She told Page Six that Madonna has "never had a problem standing up for herself" and added, "She knows who she is, what she wants, what she wants to look like, what she wants to wear, what she wants to say. And I think she's strong enough to weather whatever complaints people have about her now and for always." O'Donnell also shared an anecdote from the time they filmed "A League of Their Own" together. According to the actress, men would often tell Madonna that they preferred her as a blonde (she had brown hair at that point), and the singer would simply respond, "F*** you." Given O'Donnell's knack for saying it like it is, it's no wonder these two get on so well!