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Along with being a popstar, Madonna starred in several films from the late ’80s into the early 2000s. Among her greatest successes on the big screen was her role in the 1992 classic, A League of Their Own.

While the film is one of the era’s most beloved comedies, it seems there was plenty of comedy involving the pop superstar behind the scenes as well. 

Madonna as ‘All the Way’ Mae in ‘A League of Their Own’

Playing Mae Mordabito, aka “All The Way Mae,” Madonna was one of the biggest names attached to A League of Their Own. (Geena Davis and Tom Hanks also signed on). However, much of Madonna’s time on set was spent with newcomers Lori Petty and Rosie O’Donnell. 

Petty had just finished filming what would be her breakout role as Tyler in Point Break. She was not yet considered a big name in film. When it came time to assign makeup trailers, Petty told The Hollywood Reporter that director Penny Marshall decided Petty was the perfect fit for Madonna. 

“Penny told me, ‘You’re gonna share a makeup trailer with Madonna…'” Petty recalls. “I said, ‘Penny, what the f***? Why?'” Marshall reportedly replied, “You can handle her.” Petty continued, “It was just me and a mostly naked Madonna every day for months in the makeup truck. She was really nice, and nobody works harder than Madonna. She would run six miles before work.”

O’Donnell was another unknown A League of Their Own cast member at the time. The actress would become one of the biggest stars of the ’90s, starring in movies like Sleepless in Seattle and Now and Then. But her breakout role was as Mae’s best friend and third-base woman, Doris Murphy.

A League of Their Own actress Megan Cavanagh played Marla Hooch. She told E Online that O’Donnell and Madonna were friends onscreen and off. “Rosie was not afraid of Madonna,” Cavanagh says. “[O’Donnell] did what she wanted to do, and I think Madonna loved that.”

Oftentimes, Cavanagh recalls that meant quite a show for the rest of the cast: “Rosie would sing all of ‘Holiday,’ and Madonna would get mad at her and say, ‘Don’t ever sing one of my songs again.’ And the next day, [O’Donnell would] come out and sing ‘Vogue.’ It was so fun to watch her do that.”

Madonna as an ’80s and ’90s icon

Rosie O'Donnell and Madonna smile together at the premiere of A League of Their Own
A League of Their Own stars Rosie O’Donnell and Madonna | Sonia Moskowitz/Getty Images

Recognized as one of the biggest names in music, Madonna’s career took off in 1983 with her album, Madonna. The singer followed it up with several more successful albums before the decade’s end including 1984’s Like a Virgin,” 1986’s “True Blue, and 1989’s Like a Prayer.” 

Meanwhile, Madonna began her acting career in 1985 with Desperately Seeking Susan. The Queen of Pop did a series of less-successful movies before landing the starring role in 1990’s Dick Tracy opposite Warren Beatty. By the time she was cast in A League of Their Own, Madonna was a bona fide superstar. 

The new ‘A League of Their Own’ series

The beloved film is now being rebooted as a series, A League of Their Own. It will premiere on Amazon Prime on August 12, 2022.

As reported by Entertainment Tonight, “The reboot introduces a new generation of women who dreamed of playing professional baseball, both in and outside of the All-American Girls Baseball League in the 1940s.”

The reboot will also see the return of at least one member of the original cast: O’Donnell as a local bar owner, Vi. But there is no word yet on if Madonna will be bringing “All the Way” Mae back for a cameo.