The Hilarious Way Madonna Helped Rosie O'Donnell Book Sleepless In Seattle

Madonna and Rosie In A League of their Own

They say show business is all about who you know. Word of mouth travels fast, so having a good working relationship with casts, crews, and directors will make or break a new star's career. One such actress who learned this early on is Rosie O'Donnell, who is currently starring in Showtime's new hit show SMILF. Rosie's first movie role was in the iconic baseball classic A League of Their Own, where she shared a ton of scenes with pop star Madonna. The two had a close relationship, which actually helped O'Donnell book her second movie: Sleepless in Seattle. I recently spoke to Rosie ahead of the release of Sleepless in Seattle's 25th anniversary addition, where she revealed how Madge helped her get the supporting role in Nora Ephron's classic romcom.

Well, I had just done A League of Their Own and I was hoping to get another movie role. But A League of Their Own was not out yet. And Nora Ephron's young son Jacob, who is now a grown gay man, he was in his teens, and he was a big fan of Madonna. So when Nora went to dinner that night and said to her kids 'I auditioned this young woman, I think I like her. Her name is Rosie O'Donnell' Jacob said 'Oh my god, she's friends with Madonna, I love her!' So I blame my gay icon friend Madonna and gay Jacob for getting me the role.

Well, that's a lesson learned. Never doubt the power of Madonna, because the legendary pop singer has enough connections and fans to help make change happen. For Rosie O'Donnell, it was merely being friends with the Material Girl that helped get her in the door to play Meg Ryan's best friend in Sleepless in Seattle.

Ultimately, Sleepless and A League of Their Own was a killer one two bunch for Rosie O'Donnell, and allowed her to ascend to the TV and movie icon she would eventually become. Sleepless in Seattle is one of the most iconic romantic comedies ever, and still has the ability to trigger feelings of love and nostalgia with its generations of fans. It also made $227 million on a $21 million budget, accruing two Oscar nominations along the way.

Sleepless in Seattle revolves around Meg Ryan's Annie Reed, with Rosie O'Donnell playing her friend and co-worker Becky. As Annie falls in love with Tom Hanks' character by listening to a radio show, Becky is her confidante and wingwoman in her quest for happiness. Rosie got one of the biggest parts in the movie, and rounded out a cast including Victor Garber, Rita Wilson, David Hyde Pierce, and Gaby Hoffman.

The 25th Anniversary Edition of Sleepless in Seattle is available now for home purchase, and will include special features and a new deleted scene. You can catch up on Season 1 of SMILF on Showtime's On Demand services. In the meantime, check out our 2018 release list to plan your next trip to the movies.

Corey Chichizola
Movies Editor

Corey was born and raised in New Jersey. Graduated with degrees theater and literature from Ramapo College of New Jersey. After working in administrative theater for a year in New York, he started as the Weekend Editor at CinemaBlend. He's since been able to work himself up to reviews, phoners, and press junkets-- and is now able to appear on camera with some of his favorite actors... just not as he would have predicted as a kid. He's particularly proud of covering horror franchises like Scream and Halloween, as well as movie musicals like West Side Story. Favorite interviews include Steven Spielberg, Spike Lee, Jamie Lee Curtis, and more.