The Emotional Story Behind Rosie O’Donnell’s ‘League of Their Own’ Cameo

In the sixth episode of Amazon’s A League of Their Own remake series, we meet an old friend.

Rosie O’Donnell, who starred in Penny Marshall’s 1992 film, makes an appearance as the owner and bartender of a queer-friendly speakeasy frequented by some members of the Rockford Peaches. O’Donnell played Doris, the brash and brassy sidekick to Madonna’s glamorous and boy-crazy Mae, in the original movie.

If you are a normal person like me, who has watched A League of Their Own (film version) about 63 times and can quote just about every single line, you know that Doris was the best character. That made her surprise cameo in the new series all the sweeter.

Created by Abbi Jacobson (who also stars as Carson) and Will Graham, the series expands on the premise of the film—a professional baseball league in the 1940s recruits women to keep stands filled while the male players were off at war—by layering deeper storylines of the marginalized characters that the film couldn’t, including exploring the queerness of many of the team’s players.

(Maybelle Blair, who played in the real-life league that the film and series is based on and served as a consultant on the show, came out as gay just this year—at age 95!—while her friend from those days, Terry Scott, and her partner of seven decades are the subject of the Netflix documentary A Secret Love.)

There’s an undeniable poignance to O’Donnell’s guest spot in that role in particular; the actress herself came out publicly in 2002, 10 years after the film was made. Here, she plays Vi, who serves as de facto welcome committee to queer living for Jacobson’s character, Carson. When Carson goes to Vi’s bar for the first time, Vi clocks her confused swirl of emotions: disbelief, wonder, and thrilled excitement. After their conversation, Carson almost instantly feels that everything’s going to be OK, despite her confusion over her sexuality and anxiety over what might happen if she were public about it.

The episode is an outstanding entry in an underappreciated genre: Rosie O’Donnell Is Actually a Spectacular Actress, Everyone. (Check out the HBO miniseries I Know This Much Is True as Exhibit A.) And it turns out the cameo was all the former talk show host’s idea.

While it was important to Jacobson and Graham to pay loving homage to the 1992 film—before her death, they got Marshall’s blessing to create the series—they were wary of too many on-the-nose references; chiefly, stunt casting. But, in an interview with The Daily Beast’s Obsessed, the pair says that changed when O’Donnell made a visit to the writer’s room during pre-production and pitched the idea of this character.

“I love Rosie in the movie,” Jacobson says. “There's no overt queerness in the film, even though it would have been Rosie—though she wasn’t even out at the time. But she's such an important part of American queer history. We didn’t want to do a lot of cameos, but for her to be the cameo felt right.”

While visiting the writer’s room, she pitched the creators on playing Vi and what she envisioned that the role could be, down to the wardrobe and hairstyle. Things took on added shade of poignancy, given O’Donnell’s role in the queer community, the mentorship role she voluntarily assumed with the writing staff, and the nature of the character she was going to play.

“It became the perfect, most appropriate encapsulation of the show to me,” Graham says. “It’s a show about teams that is made by a team.”

The first scene that Vi appears in, in particular, is about creating a safe space. Whether it’s a 1943 speakeasy or a hot spot in Hell’s Kitchen today, gay bars have been and still remain a hallowed sanctuary for the community. Having O’Donnell represent the origins of that was an emotional experience for everyone.

“I love queer bars and queer spaces,” Graham says. “For me personally on this show, getting to have a conversation with your ancestors on the one hand, and then your peers on the other hand about this … it was beautiful. For Carson to step into that space and realize that she's not alone and to be able to talk for the first time without worrying about being overheard, that's an experience that was described to us by some of the people that we interviewed. That felt so powerful to me.”

“The way she is revealed in the show is very much in the middle of Carson being exposed to this queer community that I do not think she thought existed,” Jacobson says. “For Rosie to be in that moment was so incredible.”

The episode was all sweet and inspirational, until, at its climax, the bar is raided by cops. Carson and her teammates scramble to run to safety without being caught—at the time, queer people arrested at communal spaces would have their names printed in the paper and be ostracized from the community. They hide out, of all places, in a movie theater that is playing The Wizard of Oz. One of the Peaches doesn’t make it out. Meanwhile, Vi is violently attacked by an officer and beaten with a baton.

They Finally Made ‘A League of Their Own’ Gay: Inside the Making of the Remarkable New Series

It’s a horrifying sequence. It’s also very real, an experience that O’Donnell knew and was eager to portray.

“The end of that episode is devastating, and is really showing the audience and Carson how dangerous it was to be queer—and how dangerous it still is to be queer in a lot of places,” Jacobson says. “That was a really important part of the queer stories we were trying to tell, so to have Rosie be a part of that was pretty special.”

When Graham was interviewing queer people who were alive at the time the story is set as part of his research, he says that many of them would have smiles on their faces—even while recounting the trauma of these raids. Survival is part of pride, and the totality of their experience is what means something to them. “I think at any point in history, we queer people find a space and a way of finding joy and celebrating with each other but there's, there's a risk to that,” Graham says.

One of his favorite stories to tell about the process of bringing A League of Their Own to life as a series is from O’Donnell. She was recounting one of her first meetings with Marshall about the project and pointed out to the director that, quite clearly to her, Doris was gay. She then did a perfect impression of Marshall’s unenthused, blunt response: “No.”

The series was a chance to make things right. And it only seemed, well, right for O’Donnell to be such an instrumental part of that.

Read more at The Daily Beast.

Get the Daily Beast's biggest scoops and scandals delivered right to your inbox. Sign up now.

Stay informed and gain unlimited access to the Daily Beast's unmatched reporting. Subscribe now.