How to share iTunes playlists

I love making compilations for my friends. Since most of my friends have entered the digital age, I no longer make cassettes and I find myself moving away from the audio CDs too. Now that most of my peeps own an iPod, iTunes, or some other kind of MP3 player, I build most of my compilations as a set of MP3s that I want to share.

It doesn’t make sense to burn an audio CD for them since it can only hold a couple dozen songs and they’ll have to re-rip it to get it into iTunes. This takes too much time and lowers the quality of the MP3. Why not give them a data disk with the whole compilation or mix ready to import?

That’s what this post is about - creating and exporting playlists for your friends. I am going to focus exclusively on making and sharing compilations in iTunes. If you spend hours coming up with a perfectly flowing playlist, you want to make sure that your friends can import your list, in the proper order, without a struggle.

1) Create a new playlist
You'll want to create a new playlist in iTunes to hold the songs that you want to share. To do this, start iTunes, choose File, New Playlist, and give the playlist a name - I called mine Femme Fatale. This is the area where you will drop your selected songs and put them in the proper order. Songs will be placed in the order that you drag them to the playlist. You can drag songs up or down the list to reorder them. Once my list is populated, I spend a lot of time playing around with the song order until I am happy with the flow.

2) Fine tuning your playlist
Once you have the songs the proper order, you may want to tweak some of the songs’ start and stop times. This can be used to play a portion of a song or to trim quiet space from the beginning or end of a song. To do this, Right-click the song in the playlist, select the Options tab, and adjust the Start or Stop times. Save the changes and listen to the song to hear your changes.

3) Duplicate Songs
OK, this may take a leap of faith for some of you, but in the end, I think you’ll appreciate this technique. Since we are going to be making a lot of changes to your MP3s, you probably want to make a duplicate set to share with your friends.

Highlight all of the songs in your new playlist, Right-click on the songs, and select Convert Selection To MP3 from the menu. Depending on the number of songs in your playlist, this may take some time. This method actually converts the songs to the format you have set in your Export Settings. If you don’t see the option to convert to MP3:

- Click on the Edit > Preferences.
- Click the Advanced tab.
- Click the Importing tab.
- On the Import Using menu, select MP3 Encoder
- Change the Quality Setting to something decent (160 or above) and click OK.

This technique will also trim the songs based on the Start and Stop times you set and it will convert AAC files to MP3 for your friends with non-iPod players like the Squeezebox. NOTE: this method WILL NOT work with DRM protected songs that you purchased through iTunes. That’s another story for a later date…

4) Find Duplicate Songs
OK, we did step #3 because we are about the alter your MP3s to change their track number, album artist, album name, etc. The first thing you should do is locate the dupes. To do this, go to your iTunes Music Library (the whole library, not your playlist) and sort the library by the Date Added column. This will bring the songs you converted to the very top. Highlight all of the songs and drag them to a new, empty, playlist - I called mine Femme Fatale FINAL. Check the new playlist and, if your songs are sorted in the opposite order, click the heading on the first column (sort order) and things should look good.

5) Clean up song information
Now we get to the fiddly bits. Some of this is tedious but, it’s going to make life a while lot easier for your friends. We need to edit information stored in each of the MP3s’ tags. To do this, highlight all of the songs in your playlist, Right-click on the highlighted songs, and choose Get Info. On the Item Information screen, you’ll want to change the following:

DO NOT CHANGE “ARTIST“! Only change the “Album Artist” field.

Album Artist - change to Various or something clever like Furious Cylon Brothers
Album - Change this to the title of your compilation (Femme Fatale)
Composer - Use same as Album Artist
Compilation - Set to Yes
Track Number - Only change the second part. For example, only change the "45" in: "x of 45".
Disc Number - 1 of 1
Artwork - If you made artwork for the CD cover, paste it here

If you do not complete these steps, the songs will not group under one album name in your friends’ library.

6) Renumber songs
One last fiddly bit… one at a time, you need to select each song, Right-click on it, and choose Get Info to set the proper track number. Make sure the track number matches the Order Number in column one. This can be tedious but it doesn’t take too long. If anyone comes up with an easier method please let me know.

7) Burn a Data Disk
Ok, you’ve done all the hard work, let’s burn a disk that your friends can import into iTunes. First, you need to check your Burning options. To do this, go to the iTunes menu and select Edit, Preferences, click the Advanced tab, and select the Burning tab. Here you want to set the disk format to: "Data CD or DVD" and click OK. If you don’t do this, iTunes will make an audio CD and all of your hard work will be wasted.

Right-click on the name of the Playlist that contains your cleaned up, duplicate songs and choose "Burn Playlist to Disk". Wait a few minutes until the disk is nicely toasted.

8) Bonus Section
OK, what did all of this hard work buy you besides happy friends and duplicate songs in your library? Well, for one thing, you can easily recreate the disk for yourself, your car, other friends, acquaintances, and coworkers.

Second, if you are like me and you have a boatload of MP3s and you’ve made many playlists for friends, it becomes hard to remember what songs you gave to whom. I save all of my compilation playlists in one folder and I built a Smart Playlist that uses them to figure out which songs I have not given away or used on a compilation. This is a real godsend.

To do this, choose File, New Smart Playlist, and set the following rules:

Playlist is not Femme Fatal and
Playlist is not Femme Fatal FINAL and…

Call the smart playlist "Songs for Friends". It will only contain songs that have not been given away. If you are really crazy (like me) you can build one of these for each of your friends.