More on playlists and syncing music to an iPod shuffle

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I get lots of questions about playlists: how to create them, how to work with them, and how to organize them. In this week’s column, I look at several questions related to playlists, and I also tackle a bonus question about syncing music to an iPod shuffle.

Q: I listen to a lot of electronic music, and have various DJ sets and albums on my iPod, but I’d like to simplify the way they’re organized. For example, I have four Dave Seaman mix albums, and each album contains around 30 tracks, but at the moment they are all in the playlist “dave seaman.” Can I have a “dave seaman” playlist, and then within that playlist have the albums in separate lists so that I don’t have to scroll through 90-odd tracks to find the album I want to play?

Yes, you can do this with a playlist folder, which is similar to a folder in the Finder, in that it can contain other playlists and subfolders.

In iTunes, choose File > New > Playlist Folder. This adds an empty folder called untitled folder. You can double-click that default name and give the folder a better name. When you click this folder, it looks like a playlist but it’s not.

You can add playlist folders to house your playlists.

Next, find the playlists you want and drag them onto the folder. You’ll see that they show up inside the folder, in an indented list, indicating that they reside inside the folder. (If they aren’t indented, that means they didn’t actually make it into the playlist and instead appear just below the folder in the Playlists list; you’ll need to drag them onto the folder again.)

After you’ve added playlists, you can click the folder to see its contents in the order of the playlists. So, all the tracks from the first playlist will appear first, then the tracks from the second playlist, and so on. You can play music from this folder by clicking the Play button (a right-pointing arrow), or you can click an individual playlist to access only the tracks it contains.

Q: I would like to give a friend a playlist I’ve made in iTunes. Is this possible? I would like for my friend to be able to download it to his iPhone.

Sharing playlists that contain music from the iTunes Store used to be possible from within iTunes, but for some reason Apple removed the feature (even though it left up a page that describes how to do so).

You can view any track that's available in the iTunes Store by clicking this menu in your iTunes library.

Now, unfortunately, the only thing you can do is to gift each track individually. To do this, hover your cursor over a track until you see a right-pointing arrow after its name. Click this arrow, and then click Show in iTunes Store.

Next, in the iTunes Store, look for the button to the right of the track name that shows a price. Click the arrow to the right of the price, then choose Gift this Song. You’ll have to repeat this process for each song, and it may take a while if the playlist is long.

Q: My wife and I each have a car with an iPod nano as a music source. Each iPod contains the same music and playlists, but my wife plays from one playlist, and I play from another. Playlist 2 was originally duplicated from playlist 1. If I uncheck a song from one of the playlists, it also gets unchecked on the other. Likewise, if I check the song anew in one playlist, it is then activated on both.

Is there a way to prevent this? Does this behavior apply only to the songs created from the playlist duplication, or does it apply to all songs we each added separately to each playlist?

Both iTunes and iOS devices ignore unchecked songs when playing playlists. So when you uncheck a song, iTunes won’t play it, and you and your wife won’t be able to play it in your cars.

This is a library-wide setting. If you uncheck a song, it will be unchecked in all playlists. If you want to avoid playing a song in one playlist, then delete the song from that playlist; doing this won’t affect the other playlist.

If you display the iTunes sidebar, you'll see your iPod or iOS device in the Devices section. You can then browse your Music library, and drag any music to the device’s icon.

Q: I have an original iPod shuffle with about 200 songs on it, selected from my modest music collection stored in iTunes. Every so often I want to change the songs on the iPod, deleting some and adding new ones from my Music library in iTunes. I used to be able to plug my shuffle into my iMac, open iTunes, and bring up my shuffle songs alongside my Music library. That feature disappeared in an iTunes revision.

How can I compare two song listings (one on the iPod shuffle and the other in my Music library, in my case) side by side so I can select and copy songs from Music to the shuffle as I used to be able to do?

It sounds like you used to open one window that displayed the contents of your iPod shuffle and another that showed your Music library. Unfortunately, iTunes 11 removed the ability to display two separate windows simultaneously.

The closest approximation to this is to display the iTunes sidebar: Choose View > Show Sidebar. You can then navigate your Music library, and your playlists, and drag any items from one of those sources onto the iPod shuffle’s icon in the sidebar.

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At a Glance
  • Pros

    • Refreshed interface
    • Up Next offer a new way to queue up music
    • Improved MiniPlayer, iTunes Store integration
    • Simplified playlist creation


    • Sort options limited in different views, many view options are hidden or inconsistent
    • Searching very slow with large libraries
    • No artwork window or option to change the size of album art in Albums view
    • No option to open multiple windows
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