Brilliant Playlists

As our music libraries swell to gargantuan proportions it can become increasingly difficult to manage the music we listen to (or would like to listen to if we could just find half the tunes we possess). Thankfully iTunes offers a leg up with Smart Playlists—a tool for automatically creating playlists that contain exactly the kind of music you want in iTunes and on your iPod.

Of course, Smart Playlists can’t do the job on their own. They need an agile brain behind the scenes to help them separate the good from the not-so. While I’m certain that your gray matter is up to the task, why strain the frontal lobe when people like me are paid to do the work for you. Put your feet up, crack open a cooling copy of iTunes, and let’s begin.

New Music All the Time

Where better to start than at the beginning? If you’re sick of hearing the same old stuff, create a new Smart Playlist that reads:

Play Count is 0.

Below you can limit the playlist by number of songs, the length in hours and minutes, or the amount of space the playlist consumes (in either megabytes or gigabytes). In the Selected By pop-up menu you can further narrow your choices by choosing songs by Album, Artist, Genre, Song Name, Highest or Lowest Rating, Most- or Least Often Played, or Most- or Least Recently Played (I believe the universe collapses in on itself if you choose Play Count is 0 and then select tunes by Most Often Played).

Be sure to also enable the Live Updating option. When you do so, iTunes will check to see what you’ve played either in iTunes or on the iPod when you next sync it and replace any songs in the playlist that have been played with tunes that you’ve never played.

The iPod mini Playlist

The iPod shuffle has the cool Autofill feature that automatically fills the little player with tracks that don’t take up a lot of space (we’ll look at Autofill in a bit). Unfortunately, Autofill doesn’t currently work with any other iPod models and, if you have a reasonably large music collection, it could be useful with an iPod mini.

Oh sure, when you plug an iPod (that’s configured to update automatically) into your computer and your iTunes library contains more music that your iPod can hold, iTunes creates a playlist of music that will fit on your iPod, 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 you own. 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 conditions that read: Kind does not contain. This list of conditions would include AIFF, WAV, Apple Lossless, and QuickTime—song formats that take up a lot of storage space. To avoid packing the mini with songs encoded at high bit-rates (the higher the bit-rate, the larger the file), ask the Smart Playlist to limit songs to those that weigh in at less than 192kbps.You’ll certainly want to exclude the Audiobooks genre and might also wish to skip such genres as Holiday and Children’s Music if its mid-July or you can’t bear one more round of “The Eensy Weensy Spider.” Finally, be sure that the top of the playlist reads Match All of the Following Conditions. If “any” rather than “all” is selected, the Smart Playlist won’t be exclusive enough—as long as one of the conditions is met by a song (bit rate, for example) the song can be used in the playlist.

If you have a lot of music on your computer and you’ve rated that music, consider adding a rating condition that reads My Rating is Greater than 3 Stars. Be sure to limit the size of this playlist with the Limit to option at the bottom of the Smart Playlist window. For an iPod mini this option should read Limit to 3500 MB selected by Album (you must use megabytes rather than gigabytes because the GB field won’t accept decimals, as in 3.5 GB).

Once you’ve created this playlist, select your mini in the Source menu, and click the iPod Preferences button. In the iPod Preferences window that appears, enable the Automatically Update Selected Playlists Only option, select the Smart Playlist you created for your mini, and click OK. The mini will be updated with your playlist—and continue to be as long as you leave this option selected.

shuffling Along

The Autofill feature that appears when you plug an iPod shuffle into your Mac or Windows PC is far smarter than the “how about I fill up your iPod with whatever I like” solution I mentioned earlier, but it could be smarter still. After creating several Autofill playlists, I was surprised to discover just how many songs in my music library run for less than a minute. I like Brian Wilson’s “Barnyard” and the Who’s “Tommy’s Holiday Camp” as much as the next guy, but I prefer that my iPod be filled with songs that are more than musical appetizers. Likewise, I don’t want to pack my shuffle with songs containing endless drum solos or large wav files (the one uncompressed format playable on the shuffle).

Also, having an iPod full of holiday music was great in December, but now that it’s nearing Valentine’s Day, I can do without visions of sugar plum fairies dancing through my head. And because I prefer that my exercise sessions aren’t interrupted with fits of laughter, any Spoken Word selections (which, in my collection, are made up largely of Eddie Izzard recordings) are out.

With all this in mind, my For the Shuffle smart playlist demands that playlist contain no WAV file, tracks are longer than two minutes (and shorter than eight minutes), and tracks tagged as Holiday and Spoken Word files are not included. I limit the playlist to 490MB because I want to know exactly what’s going to go on the shuffle rather than what might end up on it (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 leave the Live Updating option enabled.

Once you’ve created the smart playlist, simply select the iPod shuffle in iTunes’ source list and choose the smart list you created from the Autofill From pop-up menu. To refresh the contents of the smart playlist, just select everything in it and hit the Delete key to remove its contents. Because Live Updating is switched on, the smart playlist will be automatically repopulated with music.

In the Mood

Unless you’re the kind of person for which the party never ends, you’re going to want to listen to a far different kind of music on Sunday morning than was hammered into your brain the night before. To assist in this, you can create Smart Playlists that match your mood. And the key to doing so is iTunes’ Comments field. It works this way:

As you traipse through your music collection, find songs likely to work for you in particular situations—hung-over Sunday mornings or tunes that will get your blood racing while you exercise. When you find such songs, highlight them and choose Get Info from iTunes’ File menu. In the resulting window, click the Info tab and enter an appropriate word in the Comments field.

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.

Mood playlists have become increasingly important with the advent of the iPod shuffle. Because their storage space is so limited it makes sense to create playlists that will suit particular occasions—working out at the gym, playing on the subway on your way to a dead-end job, or learning a set of tunes for an upcoming gig. Again, use the comments field to classify your tunes and create mood playlists that you can choose in Autofill.

Be Exclusive

In iTunes 4.5, Apple enhanced the Smart Playlist 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’d digitized all your old phonograph albums for the sake of posterity but you didn’t want any of the songs on them to ever appear in a Smart Playlist. Sure, you could have added a “phonograph” comment to each archived song and told the Smart Playlist to not include any song with the comment “phonograph,” but would it be easier if you could simply tell the Smart Playlist to exclude all songs within certain playlists? That’s exactly what iTunes 4.5 and later does for you by including the new Playlist criterion. You can now tell Smart Playlists to harvest songs only within certain playlists.

Using our example, just place all the songs you’ve ripped from vinyl into a playlist you’ve 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.

The Subgenre Playlist

By default, iTunes provides one entry for “art” music—Classical—and lumps be-bop, swing, and fusion in the single Jazz genre. Anyone who’s familiar with such music understands that such labels are far too broad. If you’d like to classify this music more specifically, reveal iTunes’ browser, and open the Get Info window for an artist or album. In the Genre field, enter a more specific classification—Opera, Baroque, Romantic, be-bop, or cool jazz, for example—and click OK to close the Get Info window. Add genre entries for your other classical and jazz music.

Now configure the top row of pop-up menus in the Smart Playlist window to read Genre is Romantic (or some other Classical or Jazz subcategory of your choosing).

Backup Your Purchased Music Playlist

If you lose the music you purchase from the iTunes Music Store, you lose it for good and all—Apple won’t allow you to download purchased music a second time without paying for it. For this reason, you should routinely backup your purchased music. This Smart Playlist can help you do it.

Configure the top row of pop-up menus to read: Kind contains Protected AAC, give it a name such as Backup Library, and click OK. This places all the purchased music files in your iTunes music library into a single playlist. (Your Purchased Music playlist should contain these same songs but if you’ve reorganized your iTunes Music folder, it’s possible that some of the music you purchased won’t appear in the Purchased Music folder.)

Select Preferences from the iTunes menu on the Mac or from the Edit menu on a Windows PC and click the Burning tab. In the Disc Format portion of the Burning window select Data CD or DVD and click OK. This allows you to burn your iTunes files in their current format rather than converting them to a format compatible with the audio CD standard (a format that creates much larger files). Select your Backup Library playlist and click iTunes’ Burn button. If the number of files in the playlist exceed the capacity of a CD-R disc, don’t be concerned. iTunes will burn as many files as it can to the first disc and then ask for as many subsequent discs as necessary to back up everything in the playlist.

When you’ve burned that playlist, Control-click (if you have a Mac) or right-click (if you have a PC) on it and select Edit Smart Playlist from the contextual menu. Click the + button next to the top row of pop-up menus and configure the resulting row of menus to read: Date Added is in the Last 2 Weeks. Enable the Live Updating option and click OK.

If you’re using a Mac, launch iCal and create an appointment two weeks hence called Back up iTunes! Configure the appointment so it recurs every two weeks and set an alarm that reminds you to back up your playlist. If you’re using a PC, use the calendar within Outlook or an application such as Palm Desktop to create a similar alarm.

If you do lose your purchased music, open iTunes’ Preferences, click the Advanced tab, and be sure that the Copy Files to iTunes Music Folder When Adding to Library option is enabled. Insert each backup disc, select the Add to Library command from iTunes’ File menu, navigate to the disc, and click Open. The purchased music files will be copied from the disc to your computer and placed in your iTunes music library.

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.

Go Out and Make Some of Your Own

With these tips in hand, your iPod will be filled with the music you want, when you want it. But this is only a beginning. You have far greater knowledge of what your music library contains and how you’d like to listen to the music in it. I’ve offered a glimpse of what can be done with Smart Playlists, it’s up to you to take the next step.

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