When [director] Penny [Marshall] told Rosie [O’Donnell] that Madonna might join the cast, “I was like, holy shit,” Rosie says. “I couldn’t wrap my head around [it].”Penny instructed Rosie to bond with the Queen of Pop. “Rosie,” she said, “tomorrow Madonna’s coming in here. If she likes you and likes me, she’ll do the movie. Don’t mess up.”

How intimidating. Madonna was one of the most famous tabloid fixtures in the world, possibly second to Princess Diana. As a veejay in New York, Rosie wondered how a fellow esoteric comedian, Sandra Bernhard, had managed to crack Madonna’s inner circle. Wasn’t that strange? Madonna was so iconic and inaccessible. Yet Sandra broke through the ice and forged a close public friendship. Would Rosie be able to pull that off and fulfill Penny’s extraordinary request?

Before meeting Madonna, Rosie watched Truth or Dare. In the exhibi- tionist she recognized a common origin story: they both came from big Catholic families, and both were named after mothers who died young, from the same disease. Rosie had never met another adult woman who lost a mother that way.

“Hey, I saw your movie last night,” Rosie told Madonna.

“You did?”

“Yeah. And I’m named after my mother and she died of breast cancer, and I’m the oldest girl in the family.”

Boom. From then onward, they were like siblings. Penny dubbed them “Ro and Mo,” a moniker that stuck. “You’re going to be best friends,” she ordered. “Mo, you teach her how to set her hair, and Ro, you teach her how to play ball.”

Screenwriters Lowell Ganz and Babaloo Mandel got to work, beefing up their script with comedic Ro and Mo bits. With Mo onboard, Mae became brassier, more streetwise.

On June 9, 1991, the LA Times dished the unsourced news that Columbia Pictures hoped Madonna would play Kit to Debra Winger’s Dottie—a sign that within the studio, Mo supporters thought she should have a bigger role. A subsequent report corrected that she was just one of the girls.

Debra was livid. She threatened Penny, saying that if she hired Madonna, “it would be a long, hot summer,” according to [former Columbia Pictures head] Frank Price. Debra made it clear that she was going to be very difficult. Penny had blocked her from hiring new screenwriters, but Madonna was worse. Madonna was the last straw. She resented what she viewed as shameless stunt casting, a cheap and cynical betrayal of honest filmmaking. That made Penny, the betrayer, a sellout. “You’re making an Elvis movie!” she complained. When Debra agreed to do A League of Their Own, she hadn’t asked for cast approval, which she usually got. The perk was a sore subject. CAA represented both Debra and Madonna; in the mid-’80s, the former briefly left the agency to protest how it stuffed Legal Eagles with fellow client Robert Redford.

While Price surmised that Debra was jealous of Madonna, nobody mentioned Madonna’s interview in the May 1991 issue of The Advocate in which she dissed Debra’s dramatic performance in Bernardo Bertolucci’s epic The Sheltering Sky, a financial failure for Warner Brothers the previous winter. “Debra Winger was so wrong,” she told the magazine. “Oh, it was so wrong, so wrong. It was so unsexy. It was horrible.”

If Debra felt disrespected, that article certainly might have fueled her anger. In any case, Penny didn’t want to spend a long, hot summer dealing with her. “No one tells me how to cast my movies,” she griped. She asked Price for help. “Let me take care of it,” he said.

Price notified Debra’s agent, Rick Nicita, that he planned to replace her and wanted to settle her out of her deal. Debra requested a meeting to plead on her behalf. She entered Price’s office alongside Nicita and her lawyer, Barry Hirsch. Price listened as she spoke with very little interruption. “Debra, I’ve heard you for an hour,” he said. “And all I’ve heard is self-justification: how right you were in what you did. And I don’t happen to think you were right. Neither does Penny. And we can’t take the chance of bad behavior on the set.”

Columbia paid Debra about $3 million to go away.

Madonna’s arrival transformed the show into a three-ring circus. Freddie Simpson didn’t recognize her at first. Her hair was dyed brown, and she seemed smaller in person. Madonna changed her look at the speed of light, though her “Material Girl” video, in which she impersonated Marilyn Monroe, cemented the chameleon’s image as a sexy platinum blonde. Throughout her evolution, the thirty-two-year-old persisted in pushing buttons. A League of Their Own presented fresh targets. She kept her costars on their toes. What outrageous thing would she say next? Which truths would she point out?

In Chicago, Madonna worked harder than anyone her castmates had ever met. She rose at 4 a.m. and jogged eight to ten miles, then trained with Coach Hughes from eight to noon, then headed to the dance studio to rehearse Mae’s jitterbug number, the highlight of a complicated set piece at the fictional Suds Bucket nightclub. On the practice field one day, she told the actresses: “If anybody stays and plays until we can’t see the ball anymore, then I’ll take you to dinner.”

Megan Cavanagh, the fourth lead in her role as Marla Hooch, did not know how to act around Madonna. And Lori Petty felt awkward just saying her name.

“What are we supposed to call you?” she asked. “Because calling you ‘Madonna’ is like calling you ‘The Empire State Building,’ and I can’t do that.”

When Madonna brought a boom box on the premises, she set it down and said, “Any of you girls break it, you’re buying a new one!” “You’re richer than most third-world nations,” Rosie told her. “Don’t ask these little twenty-year-olds to pay for your boom box.”

If Mo was Queen Bee, then Ro was court jester, unafraid to razz her in good fun. Mo liked to push her body to the brink; Ro hid under the proverbial bleachers when Penny made them run three laps around the field’s perimeter. While Penny wasn’t watching, Ro would stop running and then join back up for the third lap. Penny, knowing Ro was cheating, would place her hand on Ro’s back. No sweat? She’d make Ro finish the dreaded drill.

“Penny was always screaming at me that I was playing baseball like a dancer,” Mo recalled later. “But I couldn’t help it.”

If Madonna decided that she liked you, then you felt lucky, chosen. In rehearsals for the Suds Bucket dance sequence in which the Peaches cut loose, she didn’t choose her partner, Eddie Mekka, who had played Carmine “The Big Ragoo” Ragusa on Laverne & Shirley. Penny hired Mekka, of whom Madonna disapproved. He doesn’t know how to partner, she griped to Lou Conte, their scene’s choreographer. He’s breaking my hands.

She was a tough critic. She also told Conte: “Geena Davis is the most uncoordinated person I’ve seen in my life. I don’t know how she’s gonna do this.”

At five feet, three inches tall, Eddie stood about a foot shorter than Madonna. He’d performed on Broadway, earning a 1975 Tony nomination for Best Actor in a Musical for his leading role in The Lieutenant. Good, steady gigs were hard to get after Laverne & Shirley went off the air; the work dried up. Penny, bless her, was giving him another life, but Madonna made him nervous. She much preferred the gifted Tony Savino, who led a jitterbug workshop for extras at the movie’s Prairie Street offices. When the principal cast arrived without advance warning, Savino found himself teaching dance steps to Geena and Rosie and, holy shit: Madonna. She disappeared behind a column, then reemerged, barking, “WHO’S IN CHARGE HERE?”

The room went silent. Nobody moved. Karen Frankel Jones, an original member of Chicago’s elite Hubbard Street Dance Company, pointed a finger at Savino. “He is,” she said.

Madonna and Savino started hanging out. She invited him to a birthday dinner for her assistant, Melissa Crow, at the Rosebud, an Italian restaurant on Taylor Street. He sat next to Madonna and Shep Pettibone, who produced her hit songs “Vogue” and “Express Yourself.” When Madonna excused herself to go to the restroom, it seemed that all the surrounding women diners followed her inside: that annoyed her. Melissa, an unpretentious sweetheart, opened gifts from Tiffany, and they headed to their next stop, the Baton, a nightclub north of Wrigleyville where drag queens performed. Savino knew the Baton’s owner and alerted him that Madonna and her entourage were on the way there. Rosie, Madonna’s newest wing-woman, and Coach Hughes, whom she teased for being “boring,” were along for the ride. As they took their seats on the upper level, the show began: Mimi Marks, a legend in her own right, started to perform “Vogue,” dressed as Madonna. Hughes advised the real Madonna to tip her.

Mo looked at Savino. “Do you have dollars I can tip?” she asked.

Are you kidding me? Savino thought. You’re the richest woman in the world and you’re hitting me up for money?

“I’ll pay you back,” she said as he handed her about $10 in cash. She walked down the stairs and toward the stage and tipped Mimi, who cried, “Oh, my god!” When Madonna returned to her seat, the audience glimpsed her heart-shaped face and screamed.

What is my life at this second? Savino wondered. This is unbelievable.

The lovely Ann Cusack, whom the girls affectionately called “Annie Cue,” brought her famous younger brother, actor John Cusack, to the Baton. The Cusacks hailed from Evanston, home to Northwestern University, on the city’s North Side.

“He showed up and he was, like, sitting with Madonna and hitting on her,” Savino recalls. “I’m, like, dude, really? This is not gonna happen.”

Another night, on July 7, Madonna wanted to go dancing—for fun, not work. She asked Savino to pick her up at the Zebra Lounge, a retro piano bar in the upscale Gold Coast neighborhood. Tracy Reiner was celebrating her twenty-seventh birthday there. Savino went inside and extracted Madonna and a sexy companion, who was very likely the model Tony Ward, having appeared in her racy music video for “Justify My Love.” Earlier that year, People magazine reported that she and Ward, her boyfriend since 1990, had called it quits. Whatever their relationship status, “He was stunning,” Savino says.

The three piled into Savino’s Toyota Tercel. “You need to get a car with stronger air-conditioning,” she said.

He drove them to a Black gay bar on Halsted Street, but when they arrived around 8 p.m., the place was empty. It was still early. Madonna and Savino freestyled on the dance floor; he cringed as the DJ started to spin “Vogue” in too-obvious homage. Her fellow actresses left the Zebra Lounge and followed them there, taking over the bar. Later, Savino drove Madonna back to her hotel, the Four Seasons, where Penny also stayed along with Geena, Tom, and Jon Lovitz, who used the code name “Edna Poopaleedoop.” Mo (who used “Louise Oriole”) wanted a frozen yogurt, so Savino made a pit stop at a yogurt shop on busy Rush Street. While people recognized her, she wasn’t mobbed. Chicago knew when to leave a diva in peace.

Adapted excerpt from NO CRYING IN BASEBALL: The Inside Story of A League of Their Own: Big Stars, Dugout Drama, and a Home Run for Hollywood by Erin Carlson. Copyright © 2023. Available from Hachette Books, an imprint of Hachette Book Group, Inc.