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As our iTunes libraries swell to gargantuan proportions, it can become difficult to manage the music we listen to (or would like to listen to if we could only find it). Thankfully, iTunes offers a leg up with the Smart Playlists feature, which lets you create dynamic playlists containing exactly the kind of music you want in iTunes and on your iPod. But to do their job well, smart playlists need your help.

New Music All the Time

iTunes’ Play Count feature keeps track of how many times you listen to individual tracks. If you’re sick of hearing the same old stuff and want to start exploring the deeper recesses of your music library, start by creating a smart playlist that reads Play Count Is 0 (See top screenshot). Then you can limit the number of songs in the playlist or the playlist’s length (in either hours and minutes or by the amount of space the playlist consumes). In the Selected By pop-up menu, you can further narrow your choices by telling the playlist to pick songs by Album, Artist, Genre, Song Name, Highest or Lowest Rating, Most or Least Often Played, or Most or Least Recently Played (although the universe may implode if you choose Play Count Is 0 and then select Most Often Played). Be sure to enable the Live Updating option, so iTunes will check to see what you’ve played (in iTunes or on the iPod) when you next sync your iPod. It’ll then replace any listened-to songs in the playlist with tunes you’ve never played.

Be Exclusive

In iTunes 4.5, Apple enhanced the Smart Playlist feature in an important way. Previously, there was no easy way to keep sections of your library from appearing in a smart playlist. For example, let’s say you’ve digitized all your old records for the sake of posterity but you don’t want any of the songs on them to ever appear in a smart playlist. Sure, you could add a “vinyl” comment to each archived song and tell the smart playlist not to include any song with that comment, but wouldn’t it be easier if you could simply tell the smart playlist to exclude all songs within certain playlists? Well, with iTunes 4.5 and later, you can.

In this example, just place all the songs you’ve ripped from vinyl into a playlist called From Vinyl. Then configure a smart playlist so that it reads Playlist Is Not From Vinyl. From there, you can further narrow down your choices by including or excluding other playlists.

Shuffle Along

The Autofill feature Apple created for the iPod shuffle works more intelligently than a “how about I fill up your iPod with whatever I like” solution—but it could be smarter. For example, I like Brian Wilson’s “Barnyard” as much as the next guy, but I prefer that my iPod be filled with songs that are more than seconds-long musical appetizers. Likewise, I don’t want to pack my shuffle with songs contained in large WAV files (the one uncompressed format it supports), with holiday music during the summer, or with comedy routines when I’m heading to the gym.

So I built a smart playlist made up of tracks that were longer than two minutes (and shorter than eight minutes), that were not WAV files, and that were not tagged as Holiday or Spoken Word (See bottom screenshot). By limiting the playlist to 490MB, I was able to see exactly what was going to go on the shuffle (if you leave the Limit To option disabled, Autofill will choose a subset of tracks from a potentially much larger playlist of songs). As with my other smart playlists, I left the Live Updating option enabled.

Once you’ve created a smart playlist you like, select the iPod shuffle in iTunes’ source list and choose the new playlist from the Autofill From pop-up menu. To refresh the contents of the smart playlist, just select everything in it and press the delete key. Because Live Updating is switched on, the smart playlist will automatically repopulate with music.

View Your Purchased Music

Although the Purchased Music playlist that iTunes creates the first time you buy something from the Music Store should contain all your purchased songs, it doesn’t always. Reinstalling iTunes or reconfiguring your music library can confuse the playlist and make it forget that you bought those songs. However, you can create a smart playlist that never forgets. Configure the top row of pop-up menus in a new smart playlist like so: Kind Contains Protected AAC. Give it a name such as Backup Library, and click on OK. All the purchased music files in your library are now in one playlist.

The iPod Mini Playlist

Many people—especially those who own iPod minis—wish that the iPod shuffle’s Autofill feature worked with other iPod models. If your iPod is set to update automatically, and if your iTunes library contains more music than your iPod can hold, iTunes will create a playlist of music to fit—but iTunes isn’t discerning about what it puts in that playlist. It’s just as happy to copy huge AIFF, WAV, Apple Lossless, and audiobook files to your iPod as it is to grab the tiniest MP3 and AAC files. If you want to pack as much music as possible onto your mini, you need something smarter.

With that in mind, create a series of Kind Does Not Contain conditions for AIFF, WAV, Apple Lossless, and QuickTime files—which take up a lot of storage space. Then, to avoid packing the mini with songs encoded at high bit rates (the higher the bit rate, the larger the file), limit your playlist to songs that weigh in at less than 192 Kbps.You’ll certainly want to exclude the Audiobooks genre as well. Finally, be sure that the top of the playlist reads Match All Of The Following Conditions.

If you rate your music, consider adding a rating condition that reads My Rating Is Greater Than number of stars. Be sure to limit the size of this playlist with the Limit To option at the bottom of the Smart Playlist window. For a 4GB iPod mini, this option should read Limit To 3500 MB (you must use megabytes rather than gigabytes because the GB field won’t accept decimals, as in 3.5GB).

Once you’ve created this playlist, select your mini in the Source menu and click on the iPod Preferences button. Now enable the Automatically Update Selected Playlists Only option, select the smart playlist you created for your mini, and click on OK. Now the mini will update with your playlist.

In the Mood

Unless you’re the kind of person for whom the party never ends, you’re going to want to listen to a far different kind of music on Sunday morning than on Saturday night. A great way to do so is to use iTunes’ Comments field to create smart playlists.

As you traipse through your music collection, find songs for particular situations—mellow sounds for hungover Sunday mornings, or energetic tunes that will get your heart pumping while you exercise. Select multiple songs and choose Get Info from iTunes’ File menu. In the resulting window, click on the Info tab and enter an appropriate word in the Comments field (

, for example).

When you’re ready to compile your playlist, configure the top row of pop-up menus to read Comment Contains whatever, where whatever is the mood or situation you’d like a playlist for—Comment Contains Exercise, for instance. Because of its limited storage space, mood playlists are great for the iPod shuffle.

The Audiobooks Playlist

The fourth-generation iPods, iPod minis, and iPod photos place audiobooks in their own special playlist. If you have an earlier iPod, you can fake an audiobooks playlist. Just configure the top row of buttons to read Genre Contains Audiobook.

[ Contributing Editor Christopher Breen is the author of Secrets of the iPod and iTunes , fifth edition (Peachpit Press, 2005). ]

Probe the depths of your iTunes library by access-ing tracks you’ve never listened to.The iPod shuffle’s Autofill feature is nice, but you can do better with a smart playlist.
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