Quote:
Originally posted by Wildcat
I need advice, fellow Medonsters  . This obscure record store from my city is selling used Madonna CDs for $13 each (some of them are japanese imports). The owner doesn't have knowledge of pop culture whatsoever so I wanted to ask y'all which singles are the rarest so I can purchase them a$ap
CD Catalogue
Angel / Into The Groove
Dress You Up
La Isla Bonita (Super Mix)
Who's That Girl
Causing A Commotion
Remixed Prayer Mini Album (JP)
Keep It Together
Hanky Panky
Rescue Me (Digipack)
Ultra Rare Tax (Bootleg)
Total Satisfaction (Bootleg)
This Used To Be My Playground
Erotica
Deeper And Deeper (Digipack)
Bad Girl
Rain
Bye Bye Baby
Secret
Secret (The Remixes - JP)
I'll Remember
Take A Bow
Bedtime Story
Human Nature
You'll See
Don't Cry For Me Argentina
Don't Cry For Me Argentina (Remixes)
Another Suitcase In Another Hall
You Must Love Me
Frozen
Ray Of Light
Drowned World
Beautiful Stranger
Music
Don't Tell Me
American Pie
What It Feels Like For A Girl
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Time to spend your shekels on mountains of Madonna.

You've found the mother lode! Kind of.
Angel, Dress You Up, Who's That Girl, and Causing A Commotion are all scarce and worth more than $13 apiece. I'd posit that you could easily get two or three times that for each one of these, really. Perhaps even more.
Generally, most every CD single pre-Like A Prayer will be at least somewhat rare. Almost all stock copies of the singles before then were either vinyl records or cassettes. Many of Madonna's hits of the '80s were never released as compact disc singles at all until 1995, when the German record label put out a series of 23 CDs featuring resized artwork taken from the original 7" and / or 12" maxi-single pressings. These were reissues, but on a brand new format.
The four I've mentioned above are all from this collection, as these particular titles you've mentioned weren't issued as CD singles at any other time.
I'd also recommend the Japanese releases, especially if he's selling them with their obi strips intact: Super Mix (this could be Australian, too, but it doesn't really make a difference), Remixed Prayers, Secret Remixes, and any other title he's got. Pretty much all of her releases from that country are sought by collectors, but bear in mind that an item's value can REALLY diminish without its obi!
Bye Bye Baby is kind of hard to find as it was only issued as a regular CD single in Australia and in certain European countries. The European one, pressed in Germany, is slightly more common, but they're both scarce and a bit valuable (~$25?). No matter which version he's got, it could be worth grabbing.
All of the others are quite common and can be found online quite easily and, in most cases, for a lot less. By the '90s, cassingles and vinyl records were getting to be less common as compact discs really took over the market. Naturally, with so many of them in existence today, they're not going to command premium prices. For what he's asking, I personally wouldn't buy any of the ones I've left out. You can nab them for cheaper elsewhere.
