Debra Winger Just Shared Her Brutally Honest Thoughts About Madonna, And They’re Not Pretty

In 1992 acclaimed actress Debra Winger shockingly dropped out of A League of Their Own. The star had just spent three grueling months training with the Chicago Cubs so that she could convince audiences in the role of a woman baseball player. Then, all of a sudden, she quit the film. She never publicly explained why, either... until now. And when Winger revealed the stunning story, superstar singer Madonna did not come out of it looking good.

Play ball

Winger had been penciled in to take the part of Dottie in A League of Their Own, which was directed by Penny Marshall. In the end, though, Geena Davis filled the role. The character had its inspiration in Dorothy “Kammie” Kamenshek, who really did play for a women’s baseball team many years ago. But Winger didn’t have a bad word to say about Davis.

No love lost

Not that that would have been too surprising. Winger is somewhat prone to feuding with her costars, after all. She famously fell out with Shirley MacLaine when making Terms of Endearment, the 1983 hit. The love they showed one another in the movie was definitely not echoed in real life! Some of Winger’s behavior showed genuine contempt for her fellow star, too.

Grinding Gere

And a year before Terms of Endearment, Winger had experienced an uncomfortable few months making An Officer and a Gentleman. She didn’t like co-star Richard Gere one bit, labeling him a “brick wall.” She liked director Taylor Hackford even less – naming him an “animal.” The star has even acknowledged she had a reputation as “difficult.” But she insisted that was not why she quit A League of Their Own.

Humble beginning

Mind you, the actress had come a long way from her days as a part-time worker in an amusement park. That job had ended when an accident left her blinded for a few months. She decided carny life was not for her and instead set her sights on show business, where she eventually found herself in minor roles and on one occasion in a more, shall we say, adult film.

Big break

In 1980 Winger had her breakthrough when she grabbed the sought-after role of Sissy in Urban Cowboy. Her next film wasn’t a success, but her voice had caught the ear of Steven Spielberg. He asked Winger to voice the alien for the original edit of his 1982 film E.T. the Extra-Terrestrial and she happily obliged, although it’s Pat Welsh’s voice that was mostly used for the final cut. 

Oscar nod

Winger even showed up in E.T., although her face was obscured by a mask. There was no hiding in An Officer and a Gentleman, though: she set the screen on fire when she appeared alongside Gere. In fact, she even caught the eye of the Academy, receiving a nomination for Best Actress for her role in the movie. 

Not so endearing

The next year, Winger was nominated again, this time for Terms of Endearment. By this stage, though, talk of her being difficult had started to spread. Still, with her acting chops and the success of her films, producers were more than happy to cast her in their movies. But she mostly gave the roles that she was offered a pass.

Faltering career

The roles that Winger did take on didn’t work out especially well, either. Because although she was praised for her parts in movies such as Legal Eagles and Black Widow, the pictures are not really in the cultural conversation anymore. So by 1992, when A League of Their Own was on the cards, you’d have thought Winger would be ready for a new taste of success. But she hadn’t count on the Madonna of it all...

Seeking success

Madonna was slated to be Winger’s co-star in A League of Their Own. She’d had an up-and-down film career herself before that point. She’d begun well in Desperately Seeking Susan. In that film, she played a woman not too far removed from herself – and it went down well with audiences. But that feeling wasn’t to last.

Shanghai stinker

A couple of flops followed, with 1986 stinker Shanghai Surprise seeing Madonna play against type as a missionary. Who’s That Girl showed her back in her groove as a kooky vagabond, but although Madonna was fine in the role, the film wasn’t all that well-received by either critics or audiences. Still, she didn’t seem to be blamed for it, given that her career continued to flourish.

On the up

Next Madonna graced Dick Tracy as a singer in 1990. Pretty apt casting given her day job, and she got to showcase some new songs in the movie. And even Woody Allen was impressed enough to give her a role in 1991’s Shadows and Fog, where U.K. newspaper The Guardian’s critic felt she “[held] her own” in company that included superb actors John Malkovitch and Mia Farrow.

Star turn

So the singer was quite a catch – no pun intended – for Penny Marshall when she was cast in the comedy A League of Their Own. Madonna was at the peak of her acting and singing powers, and Marshall doubtless expected a zesty and fun turn from the star. She got it, as Madonna nailed the role of Mae Mordabito.

Sex sells

It was downhill from there, though, for Madonna. In the next year, a steamy obsession saw her pursue projects that leaned hard a more adult kind of entertainment. The film Body of Evidence, for instance, aimed to capitalize on a trend set by Basic Instinct – but only turned audiences off. But that didn't stop the “Material Girl” from feuding with celebrities.

Cher clash

One of the longest-running tiffs is with Cher, who may not have been too happy about the new kid on the block. She admitted that she didn’t like Madonna, whom she described as “mean.” And after a trip to her house, she described her rival as “a spoiled brat.”

Patti pouts

Another famous face who turned out not to be a fan of Madonna was Patti LuPone. On Watch What Happens Live With Andy Cohen in 2017 LuPone let fly, saying, “Madonna is a movie-killer. She’s dead behind the eyes. She cannot act her way out of a paper bag.” Brutal stuff, but what another top singer had to say was maybe even worse.

Elton angry

That was Elton John, who gave Madonna both barrels at the Q Awards in 2004. She won Best Live Act, and the diminutive Englishman was incensed. He announced, “I think everyone who lip syncs on stage in public when you pay like 75 quid to see them should be shot. Thank you very much. That’s me off her Christmas card list, but do I give a toss? No.”

Gaga feud

Madonna’s ego also bumped up against Lady Gaga’s, and the result wasn’t pretty. She claimed that Gaga’s music was not much more than a copycat of her own. Her Ladyship showed class in her response, simply claiming that they were different artists, although she did note on British radio in 2016, “I just will not be compared to anyone any more.”

Jacko jilted

Another singer who found himself on the wrong side of the “Like a Virgin” star was Michael Jackon. The King of Pop told his spiritual guru Shmuley Boteach that she was “not a nice person” and a “nasty witch.” Sister Janet rode to Jackson’s defense too, telling Vibe magazine in 1994, “If I did hate [Madonna], I’d have valid reasons.”

Divas detonate

If that wasn’t enough, Madonna had a diva-off with Mariah Carey. She told Spin magazine in 1996 that Carey didn’t make “art.” Whoops, bad move dissing Mariah! She came back on MTV News that year when she said, “I really haven’t paid attention to Madonna since I was in like, seventh or eighth grade when she used to be popular, so I didn’t hear that.” Ouch!

Gwyneth grrrrr

Another famous feuder is Gwyneth Paltrow. The two were big friends until they fell out. Paltrow claimed to be delighted that her personal trainer wouldn’t be mistreated by Madonna. The diva didn’t take it well, or so an insider said. Apparently, the insider told Us Weekly magazine, “[Madonna] feels Gwyneth abandoned her. Now Madonna will do anything to make her suffer.”

Purple patch

Yet another feud occurred between Madonna and funk legend Prince. Apparently, they fell out over a dinner where Prince wasn’t eating to the “Material Girl” singer’s liking. She then called him a “little troll.” He fired back in a 2007 concert, saying that he had “more hits than Madonna’s got kids.”

Money machine

Still, Madonna’s not short of a hit or two herself, and clearly a talent for upsetting other stars has not hurt her brand. She’s worth not much short of a cool billion dollars, with money flowing in from her many businesses. Her share in Maverick, a joint enterprise with Time Warner, didn’t hurt, with the collaboration’s publication Sex bringing in $50 a copy for its 1.5 million-plus units sold.

Winger quits

So was it a feud that saw Winger leave A League of Their Own? After all, these are two ladies with a bit of a reputation for it. Well no – although Madonna was the cause of Winger’s departure. The star shared the story with U.K. newspaper The Daily Telegraph in August 2021.

Elvis film

When Winger heard that Marshall had casted the Queen of Pop, she did not take it lightly. She told The Daily Telegraph that she thought that this indicated that the film would become “an Elvis film.” And not wanting to be an adjunct to the Madonna juggernaut, she said adios to the movie.

Pay or play

With a decent eye for business herself, Winger still got paid. She explained, “The studio agreed with me because it was the only time I ever collected a pay-or-play on my contract. In other words, I collected my pay even though I did not play, and that’s very hard to get in a court.”

Film critic

And was the film ruined as much as Winger feared it might be? Not quite, although she didn’t feel it captured the tales of the real-life women on which it was based. She said, “As entertaining as [the final film] was, you don’t walk away going, ‘Wow, those women did that.’ You kind of go, ‘Is that true?’”

Lacked training

In the end, Winger was somewhat dismissive of the film, claiming that a lot of the cast didn’t seem to have trained enough. She was gracious about Geena Davis, who replaced her, though, saying she “did okay.” Madonna’s perfomance, though, was another matter. Winger’s verdict on that was, “I think [her] acting career has spoken for itself.”

Not begrudging

Winger pointed out that she had no problems with the cast. She said, “I certainly don’t begrudge any of them.” And there were some big names involved, including Hollywood giant Tom Hanks. He could have been starring alongside Demi Moore, Marshall’s number-one pick for the role of Dottie, but previous Oscar nominee Davis was obviously a perfectly decent choice.

Awards flowed

As it turned out, Davis won a nomination for a Golden Globe for her turn. And the film was a smash-hit, ranking number seven in takings for 1992. So the viewing audience seems to have been more impressed than Winger was. Even Madonna gained a plaudit, although it was for her song This Used to Be My Playground, not her acting.

Success again

After giving A League of Their Own a miss, Winger wasn’t much seen on the big screen. She could be caught in the Steve Martin-starring Leap of Faith in 1992 and A Dangerous Woman – for which she gained great acclaim – in the year after. But soon after that, she vanished from view.

Quitting Hollywood

Not that people didn’t want to hire the actress. No, she quit Hollywood willingly for some years. She was only 40, so very likely she could have looked forward to many more years of leading roles. Yet she stepped away from the big screen and her reason for doing so was quite simple.

Disillusioned Debra

It turned out that the actress was just disillusioned with Hollywood. Winger explained to People magazine in 2017, “I don’t know what Hollywood is. I’m living under the freaking sign now, and I just stare at it and laugh. Los Angeles is a place, but the idea of Hollywood doesn’t really exist for me.”

Life challenge

And on top of Winger’s disillusionment, she had a personal life to which she wanted to devote herself. She added to People, “The parts that were coming, I wasn’t interested in. I’d already done that or I’d already felt that. I needed to be challenged. My life challenged me more than the parts, so I dove into it fully.”

Pause button

It wasn’t a permanent end to her film career, though. She told People that she’d just “pushed the pause button.” She had married Arliss Howard, and she’d soon have a child with him: Babe. He was her second, her first being with Hutton. It was definitely worth her while: she was still married to Howard in 2021.

Motherhood focus

And Winger didn’t just take it easy during her break of six years. On top of mothering and taking pleasure in being at home, she did some repertory theater and work for charity and as an environmental activist. In 2010 first son Noah told The New York Times, “She’s a very good, very thoughtful mother, and I think it was hard for her to bring the commitment to her work that it requires when we were young.”

Back to work

Winger came back to the big screen in 2001 when she starred in Big Bad Love. But she found it hard. She told People magazine, “I don’t know that I would advise anyone to step back the way I did. I had a very insightful friend who warned me back when I stopped reading scripts, ‘It’s easier to change directions while you’re still moving.’ If you stop, it’s harder to get started again.”

Small screen

The actress is more often seen on the small screen these days. For four years, she tickled funny bones in Netflix comedy The Ranch. Now, at the time of writing, Winger is delighting audiences on streaming service Apple TV+, for whom she stars in the series Mr. Corman. Not that she’s completely a stranger to films: she starred in The Lovers in 2017.

Star power

As for Madonna, she went on to gain acclaim in Evita in 1996. Despite the harsh words of Winger, the pop star scored a Golden Globe for her acting in that film. But after she was given a massive critical thumbs-down for 2002’s Swept Away, she more or less quit acting, with her final film appearance being in the same year’s Bond movie Die Another Day.

Recording success

And it’s never been Madonna’s main gig: that’s still her music. She’s shifted more than 300 million records across the globe, which ranks her among the top-performing female recording artists of all time. So having a reputation as being “difficult” is not the be-all and end-all it once was.