Gonzus

Which singles are It's so cool and Autotune baby be-sides to?

I wouldn't called them "obscure" since they were performed live.
I'd pick Candy Shop. The thing with this song is 1) the production sucks, it has nothing to do with her style (the whole album); 2) it's too mid-tempo, I would speed it up a bit. 3) the chorus is a banger, whereas the verses suck and don't connect with the chorus at all; 4) the lyrics are cringey. In spite of all this, I prefer this song.
When it comes to Body Shop, I found the production very good, I would say it's quite innovative sonnically. The melody is good, cohesive. But the song fails because her vocals are a girlish put-on that I find irritating very quickly. Yet, it sounds incredibly sincere, honest and tender. Just another of those Madonna's contradictions.

Body shop lyrics are embarassing ... and in any good way possible. The mood and the melody are cute so it's a shame.
Candy shop is a solid track, very Neptunes sounding, and always a stand out moment when performed (my favourite version musically is the MDNA one, in terms of performance SS and RH were both energetic and sexy). She's been able to make it something in her career even without a proper release or success.

I think DSS is a bit overrated as a film. I watched it again recently and I found it boring, slow, silly and utterly dated. Everybody's gonna hate me for this, but I have to say it. 

I know, I watched it 15 years ago. The film's dialogue is entirely sung as recitative, including casual conversation, and is sung-through, or through-composed, like some operas and stage musicals. I agree with you in that Evita is a bore, but she lobbied a LOT to get good reviews and did. 

Who's That Girl Tour. 

Who's That Girl Tour. 

She actually could have been good in Chicago. In other movies definitely not.
Let's face it,  a successful movie doesn't mean a successful acting. The Matrix could have been a hit with Madonna, but she would have been a stiff Dita with some awkward accent. 
BTW I think she only wanted to act in Chicago. They didn't offer her any role.

She was bad in Shanghai Surprise, not just the movie itself.
WTG is one of those cute comedy movies. It is mediocre, like Madonna's acting, but people gave it too much hate, considering there were many similar movies in the 80s. It is one of those fun movies where I don't care about the acting. It is a comedy, so nobody should expect actors to deliver some Oscar level acting. Worse comedy movies are done these days and aren't dragged for bad quality.

Also, Madonna has a problem with someone else telling her what to do. And when she listens, like in Evita, she is good.
If you didn't notice, she played pretty much the same characters. Young, sexy, cool... You can't be an actress and stick to the same roles that show how pretty you can be. 
There was a rumor she was insulted when Britney asked her to play her mother.

I loved this elegant, feminine Madonna

It is the truth. It is a silly movie that has a cult status. It is basic, but we usually talk about Madonna being good in it and not the quality of the movie.

LOL, the lenses, the rabbit teeth, the orange hair and the pregnancy-fat face. Her face was plump when it should have been gaunt

I loved this elegant, feminine Madonna

I loved this elegant, feminine Madonna

I can't believe no one has mentioned her in my favourite Madonna film... Bloodhounds of Broadway. She was wonderful in that role and showed some vulnerability and depth in the character she was portraying. That role and the film meant a lot to her, considering what the director was going through and she was really there for him, as I think the rest of the cast and crew were in his final weeks.
Woody Allen, Tarantino, Spike Lee, all worked with her as well later on. Swept Away was the final straw though and I think that really broke her. And that's over 20 years ago. She would be great in so many of the television roles that have come about in those twenty years. But every time she took on a role she has something to prove and that must be a terrible burden for anyone; that everyone has already made their minds up that you're going to fail. Here in the UK, they referred to her as "the plank" because she was so wooden. 
She would've been great in the silent era though; those eyes 💜

I hate you for this 

I think DSS is a bit overrated as a film. I watched it again recently and I found it boring, slow, silly and utterly dated. Everybody's gonna hate me for this, but I have to say it. 

I think DSS is a bit overrated as a film. I watched it again recently and I found it boring, slow, silly and utterly dated. Everybody's gonna hate me for this, but I have to say it. 

And Vera, from Die Another Day.

That's wahy Truth or dare is her best movie, because she plays herself to the hilt. But I think she becomes someone else in Dangerous Game.

Evita was a bore, but she was good in it. But I think Dangerous Game was her best performance ever, followed by the character she portrays in the Bad Girl video. Evita comes next, then Susan. 

I dare to say that she was good in Swept Away. And in retrospect she was not so bad in Who's That Girl. Body of Evidence was tragic, the entire film. Her performance was robotic and cold while her look/wardrobe were terrible, but the other actors were awful too. I think she was channeling Dietrich's Witness for the Prosecution. She made a fool of herself and was funny when it was not intended; the candle scene was lame and laughable and the line: "That's what I do, I fuck" was appalling. But her worst film ever was "Shangai surprise", I couldn't finished it. Dick Tracy was a bore beyond belief, but she comes off as a very convincing Marlene Dietrich (again), meaning she is a stunning presence but nothing else in that film. She actually steals the film, overshadowing the other actors.

Finally! I absolutely agree

I totally agree