Levon

I suppose that Madonna was not quite so happy with WTG, which some critics saw as a rip-off of La Isla Bonita and only floated on its wave of success. Maybe that's one of the reasons why they preferred to keep the song exclusively on the soundtrack, which sold fantastically, but also remembered of the flop of the movie. LAP established Madonna as a serious artist and so they decided to go with Cherish, because her then current successful studio album couldn't be represented by only two singles. Maybe they also picked Cherish to compensate for the loss of the musically similar song True Blue, which also sold better than Cherish - but five True Blue singles would have been simply overweight. By holding back a few gems (True Blue, Dress You Up, Who's That Girl, Gambler, Angel, Causing a Commotion & Keep it Together), they also supported the sale of the albums they contained. By leaving them out, they probably made more money than if they had put them all on a double album. Of course it was disappointing for many fans, but the new two tracks dried every tear.

That's right. On the other hand, with Into The Groove and Crazy for You, there might have been problems with the rights at that time and the focus for this collection was to focus on the faster songs. After all, in the final version the bigger hit Who's That Girl was kicked out for Cherish. However, maybe it was just an ordinary Japanese promo compilation that happened to come out shortly before TIC. One year before, the Japanese promo "1983 - 1989" was released (without Vogue). https://www.discogs.com/Madonna-1983-1989/release/2932457?ev=rr

Before Immaculate Collection came out there was this Japanese promo greatest hits. Maybe this tracklist was the original tracklist consideration. https://www.discogs.com/Madonna-1983-1990/release/2932474

Like A Virgin/Billie Jean Possessive Love or Scheherazade?

Who’s That Girl Spanish Eyes or Something to Remember?

Sidewalk Talk Crimes of Passion or The Game?

Erotica Physical Attraction or Living For Love?

Latte Never Let You Go or Alone With You?

At the beginning I'm Breathless was considered as a "proper album", even Who's That Girl was called "Madonna album" by Warner - Madonna just hadn't released that many albums yet and no particular differentiation was made between studio album, compilation and soundtrack. Such categorization came up later with Evita. Suddenly I'm Breathless was "just a soundtrack".

Your Honesty Freedom or Let Down Your Guard?

The album is similarly difficult as Evita, which has the strongest impact as a whole, but loses its power if you break it up into the individual songs. I miss the easiness of COADF / True Blue / Music and also the cohesion of American Life / Erotica / Ray of Light. Stuart Price might have added some more structure to the chaos, but clarity wasn't Madonna's concept this time. At the moment I only listen to Looking For Mercy, Crazy, I Rise (Laibert Remix) and Crave (Benassi Remix). It is still difficult for me to classify the album - it's a beautiful mess.

Your Honesty Santa Baby or Jimmy Jimmy?

R&R was the first Madonna release I didn't buy. On Ebay there are much better bootleg compilations than this travesty.

Technically The Immaculate Collection was already a remix album - and it's her #1 album. I'd like a concept like that for an upcoming Greatest Hits Collection, only that the songs should be pimped up a lot more. Stuart Price has already been mentioned - he would be the right man for such a "The Immaculate Collection - Revived". The super deluxe version needs a 4-CD set (incl. remixed/refreshed ballads).

Papa Don’t Preach Stay or Iconic?