Creating and Configuring a Playlist
If the iPod were like lesser music players, you'd have to select all the songs on the device from one enormously long list. Thank heaven Apple's engineers had more sense than to provide you such a limited interface. Among other options, you can navigate your iPod via the playlists you create in iTunes. Here's how to create a variety of playlists.
Standard Playlists
You can create standard playlists in iTunes 2, 3, and 4. Follow these steps:
1. Click the large plus-sign (+) button in the bottom-left corner of the iTunes window (Figure 2.13), or choose the New Playlist command from the File menu (Command-N on the Mac, Ctrl-N in Windows).
Figure 2.13. Click the plus sign (+) to create a new playlist.

Figure 2.14. Naming a new playlist.


Playlist from Selection
iTunes 2, 3, and 4 also allow you to create a new playlist from selected items. Here's how to create such a playlist:
1. Select the songs you'd like to appear in the new playlist.To select multiple items in a row, click the first item you want in the playlist and then Shift-click the last item. All the songs between (and including) the songs you clicked are selected.2. Choose New Playlist from Selection from iTunes' File menu.A new untitled playlist containing all the selected songs appears in the iTunes Source list.3. To name the playlist, type the name in the highlighted field.
Smart Playlists
iTunes 3 introduced the Smart Playlista playlist based on user-generated criteriaand that feature remains in iTunes 4, albeit with some interface changes. When you invoke the New Smart Playlist command in iTunes 3, you get a window that contains two tabs: Simple and Advanced. iTunes 4 dispenses with this tab structure and instead presents the Advanced interface. Smart Playlists are not available in iTunes 2. Here's how they work:
1. Choose New Smart Playlist from iTunes' File menu.If you're using iTunes 3, you'll see two tabsSimple and Advancedin the resulting Smart Playlist dialog box. To create a simple Smart Playlist, make sure that you're in the Simple section of the Smart Playlist dialog box.If you're running iTunes 4, you'll see no tabs.2. Choose your criteria.In iTunes 3, you'll spy a pop-up menu that allows you to select songs by artist, composer, or genre, followed by a Contains field. iTunes 4 offers more selection criteria. To choose all songs by Elvis Presley and Elvis Costello, for example, you'd choose Artist from the pop-up menu and then enter Elvis in the Contains field.You can limit the selections that appear in the playlist by minutes, hours, megabytes, gigabytes, or number of songs. You may want the playlist to contain no more than 1 GB worth of songs, for example.You'll also see a Live Updating option. When it's switched on, this option ensures that if you add any songs to iTunes that meet the criteria you've set, those songs will be added to the playlist. If you add a new Elvis Costello album to iTunes, for example, iTunes updates your Elvis Smart Playlist automatically.3. Click OK.A new playlist that contains your smart selections appears in iTunes' Source list.
To create an advanced Smart Playlist in iTunes 3, choose New Smart Playlist from iTunes' File menu, and click the Advanced tab in the resulting Smart Playlist dialog box.iTunes 3's advanced Smart Playlist is the same as iTunes 4's regular playlist and allows you to choose songs in many ways (Figure 2.15). You can, for example, select songs by album, artist, bit rate, comment, date added, last played, genre, or play count. Clicking the plus-sign (+) button next to a criterion field allows you to add other conditions. You could create a playlist that contains only songs that you've never listened to by punk artists whose names contain the letter J.
Figure 2.15. iTunes 4's Smart Playlist dialog box.

Proposed Playlists
Stuck for ideas on how to create smarter Smart Playlists? Sample some of these recipes:The New Music All the Time playlistSelect New Smart Playlist from iTunes' File menu, and configure the top row of pop-up menus to read Play Count is 0. If you like, enable the Limit To option, and limit the songs in your playlist by number of songs, duration of playlist, or cumulative size of the songs in the playlist (10 GB, for example). Enable the Live Updating option so that when a song has been played once, it's removed from the playlist.The iPod mini playlistWhen you plug an iPod (that's configured to update automatically) into your computer and your iTunes library contains more music than your iPod can hold, iTunes creates a playlist of music that will fit on your iPod. iTunes is the tiniest bit discerning about this playlist, in that it includes all songs on an album rather than giving you a taste of each album in your iTunes library. It's not terribly smart about using space effectively, however. It will, for example, copy AIFF, WAV, and Apple Lossless files to your iPodfiles that take up a lot of space that could be better used for storing more music files in AAC and MP3 format.For this reason, it's a good idea to create a Smart Playlist that excludes these massive songs and designate this list as the one to use when you update your iPod. To do so, create a series of conditions that read Kind does not contain. This list of conditions would include AIFF, WAV, Apple Lossless, and QuickTime. You might also want to exclude genres such as Holiday and Children's Music. 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.)When 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 playlistand will continue to be as long as you leave this option selected.The Monday Morning playlistOn the first day of the work week, it can be difficult to get the juices flowing. What you need is a heart-pumping playlist. Creating such a playlist requires a bit of planning, however. When you next browse through your iTunes music library, keep an ear cocked for tunes that are likely to get your Monday-morning groove on. When you find one of these tunes, open its Get Info window and enter Monday in the Comments field. When you're ready to compile your playlist, configure the top row of pop-up menus to read Comment is Monday.Using the Comments field is an excellent way to choose music by mood. Also consider Smart Playlists for raucous Saturday nights and hanging-around-in-bed-'til-noon Sunday mornings.The Subgenre playlistSome people find Apple's genres a little broadClassical that encompasses the music of Bach, Schubert, and Glass; and Jazz that lumps together Chet Baker with Sun Ra. Here's a technique for using an album's Comment field to create subgenres:
1. Select all the cuts on an album, and choose Get Info from the File menu to produce the Multiple Song Information window.2. In the Comments field, enter the appropriate subgenre for that music: Baroque, Bebop, Italian Opera, or Cool Jazz, for example.3. Repeat for each album in your library.
To put your efforts to work, create a Smart Playlist that uses the Comments field to distinguish musicone that reads Comment Contains Romantic, for example. To create more-specific playlists, add other terms to an album or song's Comment field. You might enter such terms as piano, concerto, and Classical to place all the piano concertos by Haydn, Mozart, and Beethoven in a single playlist.The Back Up Your Purchased Music playlistIf you lose the music you purchase from the iTunes Music Store, you lose it for good and allApple won't allow you to download purchased music a second time without paying for it. For this reason, you should routinely back up your purchased music. This Smart Playlist can help you do it.
1. 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 in 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.)2. 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 Preferences window to open the Burning window.3. In the Disc Format portion of the Burning window, select Data CD or DVD, and click OK.This option allows you to burn your iTunes files in their current format, rather than convert them to a format compatible with the audio CD standard (a format that creates much larger files).4. Select your Backup Library playlist, and click iTunes' Burn button.If the number of files in the playlist exceeds 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.5. When you've burned that playlist, Control-click it (if you have a Mac) or right-click it (if you have a PC), and select Edit Smart Playlist from the contextual menu.6. 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.7. Enable the Live Updating option, and click OK.8. If you're using a Mac, launch iCal, and create an appointment two weeks hence called Back up iTunes! Configure the appointment so that 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 window, 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 playlistThe fourth-generation iPods 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 audiobooks.The Likely Hits playlistPop albums invariably feature their strongest tracks in the number 1, 2, and 3 positions. To avoid those awful recitation-of-Elizabethan-poetry-over-soupy-strings tracks that often appear in the latter part of the album, configure the top row of pop-up menus to read Track Number is less than 4.Note:
If the album was recorded before 1980 (and, therefore, appeared originally on vinyl), consider creating a list that includes the first, seventh, eighth, and fourteenth tracks (thus grabbing the opening and closing tracks on each side of the record).The Prog-Rock Lover's playlistConfigure the top row of pop-up menus to read Time is greater than 15 minutes. Click the + button, and configure the next row of pop-up menus to read Genre is Rock (or Genre is AlternRock). Click the + button once again, and configure this row of pop-up menus to read Year is in the Range 1971 to 1979.Note:
If you're not careful, this collection could turn into The Self-Indulgent Noodling Guitar/Bass/Drum Solo from Hell playlist. To guard against this fate, you might want to add one more line of pop-up menus that reads Artist is not Grateful Dead.The Down-and-Out Country playlistCountry-music lovers know that the classics of their favorite genre have the words whiskey, truck, pool hall, and dog sprinkled throughout the librettoand that the very cream of this crop feature at least one of these words in the song title. With that in mind, create four separate Smart Playlists, each featuring one of the aforementioned magic words. Take the contents of each Smart Playlist, dump them into a master playlist, pour that playlist into your iPod, strap on the headphones, heave the dog into the truck, and head on over to the pool hall for a couple of whiskies.iTunes 4 includes four Smart Playlists: 60's Music, My Top Rated, Recently Played, and Top 25 Most Played. As their names imply, 60's Music (an homage to Steve Jobs' love for music of that decade) includes songs recorded in the 1960s, My Top Rated includes 25 songs selected at random that have a rating of four or five stars, Recently Played includes 25 songs selected at random that you've played in the past two weeks, and Top 25 Most Played includes the 25 songs you've played most often. These playlists have the Live Updating option enabled, which makes it possible for these playlists to be updated dynamically as conditions change (when you rate more songs, play different tunes, or play other tunes more often, for example).To see exactly what makes these playlists tick, Mac users can Control-click a Smart Playlist and choose Edit Smart Playlist from the resulting contextual menu. Windows users simply right-click a playlist to see this command.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. 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 ever to appear in a Smart Playlist. Sure, you could have added a "phonograph" comment to each archived song and told the Smart Playlist not to include any song with the comment "phonograph," but wouldn't 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. Now you can tell Smart Playlists to harvest songs only within certain playlists.
Playlist Helpers
iTunes 3 introduced such helpful features as ratings, the ability to pass judgment on a song by assigning it a rating of one to five stars; play count, a feature that keeps track of the number of times you've played a song in iTunes and on your iPod; and recently played, a feature that keeps track of when you last played a song. Here's a quick look at how these features enhance your iPoding experience:Ratings.
Although employing ratings is a fine way to vent your critical spleen ("I don't care how hefty a royalty it brought the composer, 'Brandy [You're a Fine Girl]' was a dreadful waste of vinyl!"), it's also quite useful. After you rate your songs, you can use those ratings as a playlist criterion.You can, for example, create a Smart Playlist that contains nothing but songs with a rating of four stars or more, thus guaranteeing that you hear nothing but your personal favorites. Or if an ill-favored cousin has planted himself on the living-room sofa for one night too many, create a playlist made up of nothing but one-star wonders, and blast it from one end of the house to the other in a repeating loop.You can assign ratings to the songs in your iTunes Library in two ways. The traditional way is to click the My Rating column in the main iTunes window and then drag the pointer to the right. This maneuver causes stars to appear in the column. Or, if you prefer doing things as inefficiently as possible, you can click a song title, press Command-I on the Mac or Ctrl-I on a Windows PC to produce the Song Information window, click the Advanced tab, and drag your pointer in the My Ratings field to produce the desired number of stars. (OK, one instance in which assigning ratings this way isn't inefficient is when you want to assign the same rating to a batch of songs. Just select all the songs to which you want to assign a rating; press Command-I on the Mac or Ctrl-I on the PC; and, in the resulting Multiple Song Information window, check the box next to the My Rating field. Now issue a rating in that field. The rating you create is assigned to all selected songs.)The other way to go about it is to assign a rating directly on the iPod. To do so, start listening to a song, and press the Select button twice. You'll be whisked to a rating screen, where you use the scroll wheel to assign the one-to-five-star rating. When you next synchronize your iPod, the ratings you've entered on your iPod are transferred to iTunes. Note that you can rate songs only on third-generation and later iPods.Play count.
The ability to keep track of the number of times you've played a song is also helpful when you want to create a playlist. One might reasonably assume that if you've played some songs more than others, those tunes hold a special place in your heart. By using play count as a smart-playlist criterion, you could take all songs that you've played more than 10 times, shove them into a playlist, andusing the batch-rating technique I mention earlier in this sidebarrate all the songs in that playlist with five stars.Or you could use play count as a way to limit the songs you've played to death. In this case, create a Smart Playlist of songs that you've never heard. Play this group of tunes when you'd like to listen to some fresh material.iTunes 3 and 4 keeps track of number of times you've played a song in the Play Count column of the main iTunes window. The iPod tracks the play count in the Top 25 Most Played playlist in the iPod Playlists screen.Recently played.
The name says it all. iTunes 3, iTunes 4, and the iPod keep track of when you last played a song. This information is reflected in the Last Played column of iTunes' main window. On the iPod, songs most recently played appear in the Recently Played playlist in the iPod Playlists screen.You can also use the recently played criterion to create a Smart Playlist comprised of fresh material (or tunes you just can't get enough of).iTunes 3, iTunes 4, and the iPod keep track of play counts and recently played status. This status won't change on the iPod, however, until you connect the iPod to your computer and update it. You can play Nick Lowe's "Truth Drug" 17 times in a row on your iPod, for example, but it won't appear in the Recently Played or Top 25 Most Played playlist until you update your iPod in iTunes. (Note that the Live Updating option must be switched on in these playlists for this feature to work.) When you update the iPod, the play-count tally increases in iTunes to reflect the number of times you've played particular tunes on your iPod.