The thing about Madonna is that she is well known for not really caring to look at the past very much. Always moving forward, so to speak. Her song has a very nostalgic vibe to it which I would assume she doesn't care to revisit.
As for her supposedly not really enjoying the making of the film - I always felt she was unfairly judged for that (gosh, the reader responses online are just brutalsome for the sake of just trashing her for being Madonna). She was venting to a friend at the time. One tiny note of frustration leaks out to the world and she got a lot of hate directed at her for that. Granted, according to Jon Lovitz, filming was brutal. The players were out in 100 degree plus heat often. Madonna was known to be on the set hours before many people and often staying a few hours after she was not needed. I heard she'd actually run a few miles first thing in the morning before the heat set in.
Madonna has since made amends of sorts with Chicagomaking nice with Oprah and visiting the city on every one of her world tours every 3 years.

Maybe revulsion - she is on record as having definitely
NOT
enjoyed making the film.

I feel the song has a deep emotional feeling for Madonna.
"A real man would rather bow down to a strong woman than dominate a weak one"

"This use[d] to be my playground" by Madonna. Strange, that is one song she has never [been] known to perform in concert.
I don't think it would be nearly as effective without the visuals.

The ending and when I hear "This use to be my playground" by Madonna. Strange, that is one song she has never known to perform in concert.
"A real man would rather bow down to a strong woman than dominate a weak one"

every time the scene comes up with stillwell angel making the bus driver quit.

Thread ender.

Cry, no, I bawled like a baby I thought it was very poignant I love this film But I'm a huge fan of all of these ladies, especially Madonna

I cry every time I see it. One of my mother's friends was a member of the league and was a consultant on the film, so I think of my mom a lot when I watch this movie.
"Life is what happens when you're busy making other plans" - John Lennon

YES! Every time I watch the telegram scene, I ball out! Also when Shirly can't read the names on the list, was also a little sad.

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The Marla Hooch and father scene(s) is the only part that makes me tear up.
http://ricoswaff.com/

Between you and me, this is one of two movies I've ever choked up over. My eyes tear up and my throat makes these noises.. Well I never get emotional and cry watching movies, but this one, and Chaplin (1992) are the exceptions. I choke up when they begin to sing (We are the members of..), and when the credits start rolling to "This Used to Be My Playground". The same goes for "Chaplin", when "Smile" is sung.. It's the music and the way it's used in movies that makes me emotional. I also weep during concerts and even when I put on certain cd's. Music is the ultimate emotional rollercoaster for me, always was..

The reunion at the end. Every friggin' time. Even just thinking about it. sniffs I may have to buy this movie.
It's the same with "Glory." I hear a little of that music and I'm done.
Probably because I saw both films at a young age.

Telegram scene. Every time.
I want the doctor to take your picture so I can look at you from inside as well.

Yes! From the time Stillwell tells Dottie that Evelyn died to the end credits I am the BIGGEST mess. I know it's coming, and that makes it even worse. And when Dottie sees that Jimmy died the year prior. Stillwell's face after he gets his picture taken with that cut-out of his mother, when he turns around and looks at her. heartbreaking. Then seeing them together, and the picture going from modern to that first season - I lose it. I pretty much only watch dark, tragic films, but few of them get me anywhere near the level of ugly crying that "A League of Their Own" does.

A few scenes choke me up, as I think it's one of the better movies out there. One scene in particular is when the boy (all grown up) gets his picture taken with a poster of his mom in the Hall of Fame.

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Yeah telegram scene is pretty bad.
But that Marla Hooch comment cheered me right up

I am a guy and I get emotional during some scenes but not the telegram scene because I think as someone else mentioned the guy delivering it was so unbelievable it ruins the scene for me. The reunion was emotional though as well as the scenes with Marla and her dad.

I cried when I saw Marla Hooch's face for the first time.
"Little bastard shot me in the ass!"

I cried when Betty found out that her husband had been killed in action.

Sure didand I'm a guy. That mail scene was (and still is) heart renching. The way the camera panned the faces of the women - with each one fearing the worst - was a masterpiece in film making.
In real life, this is happening somewhere in our country while our young men and women are engaged in combat operations in Afghanistan. A spouse, a parent, a sibling, will be getting that awful notification. We should always remember those who gave their lives for our nation.
Going back to the movie, I put "A League of Their Own" in my top-10 sports movies of all time. Great acting by all. You really feel for the characters.

I tear up a couple times during this movie. Very underrated as a film.
You're not real

Seen this movie a dozen times and still cry every time. The telegram scene starts it, then when Bob returns, the Kit & Dottie farewell scene after Dottie's team loses, and basically the last 10-15min at the reunion I'm bawling.