GhostOrchid

So madonnaunderground.nl published this dutch promo sheet advertising the upcoming Madonna greatest hits album. As noted here, Who's That Girl was originally supposed to be in, with only one new song included. 
Looking back, I wish she kept it, with 2 new songs, and Cherish kicked out.
Would you keep Who's That Girl instead of another song that made it in and if yes, which one would you kick out?

copies of artwork, no music was pressed at that stage

Actually, the reason why Holiday never got a video is because of the promotion strategy that Sire run for the album in that period .
After Holiday proved to be more successful than Lucky Star in the clubs, they decided to push Holiday to radio and stores (only in 7" form and without the cover art so the sales would go towards the album, but would be enough for it to chart on Hot 100). That would cover the dance/r&b market. 
And for the video part of album promotion they opted for Burning Up. MTV at that time was rock/new wave oriented and they got Jellybean to re-remix Burning Up in more of a rock style, for the video release to be serviced to MTV in October '83. And that was supposed to cover the rock/new wave market.
So the reason why we never got the Holiday video is because Burning Up is its video. That was the initial strategy.

This only confirms to me, I need a new era with proper costuming. How she gonna slay like this on her day off and then go back to wearing a basic red satin negligee on stage. I don't get it. 
 
Madonna on stage

 
Madonna hanging out

 

The Popular video proves that the MDNA face dildo works.  Lol. She looks amazing.  

Am i deaf or why can't i hear the Vogue sample in it? 

Why should I care about what a One-Hit-Wonder thinks about the Queen of Pop Madonna?

Sticky & Sweet tour 100%.
Was lucky enough to see it live from the fan pit, without watching any clips prior and not knowing what to expect and I was mindblown.

She's in her 'later era Picasso' phase. The art of the ugly

She's in her 'later era Picasso' phase. The art of the ugly

I quite like these. I think people are more likely to wear t-shirts with these on them than actual photographs of Madonna.

I quite like these. I think people are more likely to wear t-shirts with these on them than actual photographs of Madonna.

Maybe he made them 

Confessions and both rounds of Sticky & Sweet had the set lists printed in them.
After that, no.

Yeah, I like them as well.  It's very artsy fartsy.  Reminds me of a lot of Rocco's art. 

I agree. I would make this whole collection my 2024 uniform. 

all the songs that are performed in the show are probably mentioned in the tour book. she wanted to keep them a secret until the 1st show is over

I quite like these. I think people are more likely to wear t-shirts with these on them than actual photographs of Madonna.

Ok thanks 🙏 

Oh I agree with you, my favorite producers are Pat and Shep. True Blue, LAP and ROL are in my top 5.
I'm just saying that it's not entirely due to his musical genius. She wanted those kind of songs and he was there.
Imagine that back in 1992 she told Shep -"listen, i want 14 songs of Vogue and Rescue Me, I want to rule the charts and pop radio".  He would now be the most celebrated person by those same fans.

Someone made a good point that they deliberately left it out for the first show so that the track list isn't revealed

True, except we do know based on the interviews her collaborators gave over the years. 
Especially Pat who elaborated on every single song they did together, there's a recent interview on youtube when he was promoting his Madonna-inspired live shows. Yes, he would start with something on his piano, but she would lay a melody over it.

Madonna chooses a collaborator based on what she wants to achieve with a particular song/recording. She wanted catchy pop- she got Pat on board. She wanted raw material with deep beats- she told Pettibone how she wanted it done. 
Melodies are Madonna's own, as confirmed by almost everyone she ever worked with, and the lack of them on Erotica was a deliberate choice. Pat is an amazing musician and collaborator, but he was also lucky that those were the type of songs she wanted at the time.

Erotica is in my top six albums of all time, along with Madame X, Rebel Heart, Music, American Life, and Bedtime Stories. All 10s. The album that I have the least connection to is Confessions. I tried and tried and tried to get into it to no avail. There’s definitely something wrong with me, cause it’s universally liked.