I can't get my Mac OS 9 iTunes playlists AND music files into iTunes 9 on OS X 10.6

[mdmfennell]

I know some of you out there will probably think I'm nuts, but please read the whole message first.

I have been disabled for a number of years, and recently a friend of mine purchased for me a refurbished MacBook Pro 15" 1.83GHz Intel Core Duo laptop, which, as you might guess I love, since my last Mac laptop was the 1999 PPC G3 400Mhz that croaked about 5 years ago.

Fortunately, before that late, semi-great machine died, I was able to copy to an external drive my entire iTunes folder, which contains the "iTunes Music Library" file as well as the "iTunes Music" folder with more than 1,000 songs in it. I do NOT have any written documentation on my playlists.

Now, many years later, I have this great machine that I love, and I cannot for the life of me figure a way to import my Mac OS 9 iTunes PLAYLISTS into Mac OS X iTunes 9. Additionally, the song file folders, structured perfectly in Mac OS 9, now get recreated in truly bisarre ways in iTunes 9, where I get multiple folders by the same artist if that artist has ever done a duet with someone, and soundtracks have been broken out into individual folders by each artist on the soundtrack, instead of all the songs being placed into ONE folder with the soundtrack's name on it, as it is in the Mac OS 9 iTunes Music folder.

All I want to do is recreate my library and playlists as they were in Mac OS 9, using iTunes 9 in Mac OS X 10.6. Can someone please tell me how to do that?

Thanks.

 

[jaw04005]

Which version of iTunes are you running? The latest version for OS 9 was 2.0.4.

I’m going to assume an iTunes 2.x library can be upgraded to an iTunes 9 library. Have you tried holding down option while clicking on iTunes? Then selecting your iTunes 2 library file from your external drive?

You can turn off iTunes library management by going into Preferences -> Advanced and turning off the “Keep iTunes Media folder organized” option. However, I would recommend you let go the desire to micromanage your music library. Why do you care where or how iTunes organizes your files? Either way, you have an option.

Let us know what happens!

Update: I actually have an iMac G4 with OS 9 available. If my instructions above don’t work for you, I might play around with it tomorrow and get back to you.

 

[mdmfennell]

Thanks for responding to my post.

I was indeed using iTunes 2.0.4 in Mac OS 9.2.1.

The big[gest] difference in the two iTunes library files is that in 2.0.4, the library file is an "iTunes Database File", while in 9, it's an XML file.

I did, in fact, already have the "Keep iTunes Media folder organized" option deselected, which is how, in the new iTunes Media folder, I got several folders for the same artist if that artist worked with [an]other artist on a song. So for example, instead of having one folder for Bonnie Raitt, with subfolders for each of the three specific albums I added, I now have three different Bonnie Raitt folders: "Bonnie Raitt", "Bonnie Raitt w_John Prine", and "Bonnie Raitt w_ Sippie Wallace", which is not the case in the iTunes 2.0.4 Music folder.

And when I imported some albums that were single artist albums, they would wind up in a parent folder called "Compilations", even when they _weren't_ compilations. Unfortunately, because my circumstances prevented me from using my beloved Mac (!) for so many years, I don't know how my OS 9 iTunes Music folder came to be organised: Did I manually do everything myself and import it? (Meaning: did I import from CD into iTunes, and then get out of iTunes and sort the physical files myself? I don't recall.)

Any other suggestions or assistance would be greatly appreciated!

 

[mdmfennell]

Thanks to those of you who read my post, and to the one user who responded. As I was at the Apple Store here in Chicago I decided to learn the proper way to take care of the problem the best way I know how to learn: watch and learn. It really was merely a matter of renaming /Users/Me/Music/iTunes to iTunes.old, moving it to the trash, and copy the OS 9 iTunes folder back into /Users/Me/Music. The biggest difference is one simple naming option: /Users/Me/Music/iTunes/iTunes Media becomes /Users/Me/Music/iTunes/iTunes Music, because older versions of iTunes obviously didn't forsee anything other than "music" going into that folder.

Everything seems fine with iTunes now, but now I have another problem with Microsoft Word Test Drive self-installing that I now have to figure how to get rid of.