The Complete Guide to Album Tagging, Art and Playlists in iTunes

Jesse Hollington
By Jesse Hollington - Senior Editor
The Complete Guide to Album Tagging, Art and Playlists in iTunes

There is a lot more power under the hood in iTunes than many people realize. Beyond simply transferring content to Apple’s line of media devices, the iTunes application is actually an extremely powerful media management system in its own right. However, getting the most out of your iTunes experience may require an investment in time to actually organize the content in your iTunes library, ensuring that the proper information is filled in for your media content and building an intelligent set of playlists to help you find and enjoy your favorite music and other content more effectively.

This article provides information for both the novice and the more experienced iTunes user to help you understand how to best catalog and organize your content in iTunes, enrich it with album art, and then build playlists that reflect your own needs and interests and then transfer that information to your iPod, iPhone or Apple TV to get the most enjoyment out of your music and video content.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Tagging your Content

iTunes uses a tag-based approach to organizing your media content rather than relying on your file and folder organization. Tags are stored in your media files and contain information such as title, artist, album and genre; this provides more data than can easily be stored in a file and folder structure and since the information is contained in the files it remains available regardless of what you name the file or where you move it to.

When you import media into your library, iTunes reads these tags and copies that information into its own database for faster access. This has the advantage of allowing you to quickly locate and browse through your media content in a number of different ways, rather than being limited to the relatively rigid hierarchy of a file and folder structure. This also applies to how your music and other content is organized on Apple’s media devices: the iPod, iPhone, iPad and the Apple TV.

Of course, for this to work properly, the necessary tag information needs to have been filled in. Tracks you purchase from the iTunes Store and other online stores and tracks that you import from your own CDs will normally include at least basic tag information. On the other hand, media content that you import from other sources may not be filled in completely or properly. Further, even with your purchased and CD-imported content, you may not like the way the information is filled in and may prefer to customize it to your own liking.

Note that tag information is stored both in the iTunes library database and within your actual media files, providing the file format supports tag information. When you make a change to the tag information in iTunes, this information is updated both in the iTunes database and in the file. This means that if you reimport these files into another iTunes library or another media management application that reads tag information, any changes you’ve made will be reflected there as well. Keep in mind that some formats, such as WAV files, do not provide any fields to store tag information; in this case the information for these files will only be stored within the iTunes database and this information will not be available when importing these files into another iTunes library or another application. Users concerned about retaining tags in lossless files are probably better to consider the AIFF or Apple Lossless formats.

Viewing and Modifying Tags

You can modify the tags for any individual track simply by selecting the track in your iTunes library and choosing Get Info from the iTunes File menu.

Generally, your music tracks should contain at least the name, artist and album information to be organized properly by iTunes. Other media types can also contain this information, however fields other than the name are not always as necessary for content such as audiobooks, podcasts, or video content. iTunes uses this tag information to display and sort your tracks in iTunes and on your media devices and by default also stores your tracks in the iTunes Media folder based on these tags.

You’ll notice that a smattering of other tags are also available here. While these are basically optional, filling them in can be particularly useful for organizing and sorting your music further. For instance, iTunes and the iPod and iOS devices provide direct support for also searching and browsing your music by the Genre and Composer tags, and the Track Number and Disc Number tags are used as a default sort order for your tracks within each album.

  • Album Artist: This field is used for the name of the artist for the album as a whole, and is useful for tagging tracks from albums that have guest artists or featured artists in certain tracks. For single-artist albums, it is usually either blank or will be the same as the Artist field for the track. This is used primarily for grouping and sorting of tracks, particularly in the Grid and Cover Flow views. Recent versions of iOS can also optionally use this field to group tracks in the artist listings on the iPhone, iPod touch and iPad.
  • Year: This normally contains the year the track or album was produced. In many cases tracks downloaded from the iTunes Store or CDDB will list the year the album was produced regardless of when the original song was produced. This can be used for sorting in iTunes and is also displayed on the Apple TV. It is not shown at all on the iPod or iOS devices.
  • Track Number: This is a two-part field to list the track number and total number of tracks for an album. This is important for sorting in iTunes and on the iPod to list tracks in their proper album order. If this field is blank, tracks are sorted within each album alphabetically instead.
  • Disc Number: Similar in concept to track number, this is used for multiple-disc albums, and is used in conjunction with the track number to sort tracks in their proper order when viewing an album listing for multiple discs. This allows you to use the same album name for all discs in a multi-disc set while still having them sorted correctly.
  • Grouping: This tag is primarily used for classical pieces to group movements of the same work together during playback. For example, if you had a recording of Beethoven’s Fifth Symphony, each of the four movements may be listed as an individual track with the title of the movement itself as the track name and “Beethoven’s Fifth Symphony No. 5 in C minor, Op 67” in the Grouping field.
  • BPM: This field can be used to enter the tempo of a track in beats per minute. It is normally blank and is not used by default but can be useful as a criteria in Smart Playlists. Although the BPM field is not populated automatically, there are several third-party tools such as MixMeister BPM analyzer ( that can be used to analyze your library and fill this information in for you automatically.
  • Composer: This field lists the composer for a track. iTunes allows you to search and group by this field, and it is also available on the iPod, iOS devices and Apple TV. Although primarily useful for classical works, you will find that many contemporary pieces also include the lyricist or songwriter in this field.
  • Comments: This is a free-form field that can be used to add comments to a track. It is searchable directly within iTunes, but is otherwise not available on your media devices, with the exception of the Apple TV where it is displayed beneath the artwork when viewing audio and video tracks. For movies and TV Shows this field can be used in lieu of the description field.
  • Genre: This simply defines the genre of a track. You can either type in your own genre or use the drop-down menu to choose from a list of genres already available in your iTunes library. This is used primarily for grouping and sorting. Tt is also used to build Genius Mixes based on genre.
  • Part of a compilation: This identifies that the current track should be treated as part of a compilation album, which affects how the track is grouped and sorted in iTunes and on the iPod, iOS devices and the Apple TV. More on this later.

Viewing and Browsing your iTunes Library

Many of these tags can be displayed in the normal iTunes media listing view as additional columns. You can customize which columns are shown in the current track listing by choosing View, View Options from the iTunes menu.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Note that not all of the view options will be applicable to all content listings. Information such as Show and Episode ID, for instance, is only relevant for TV Shows.

iTunes also allows you to filter the content in your iTunes listings by displaying the column browser. Traditionally, this has been presented as three columns, for Genre, Artist and Album, above the track listing. Choosing specific entries in each column filters the columns to the right as well as the content displayed in the main window.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

iTunes 9 introduced a new layout for the column browser and chose to enable this new layout by default, for whatever reason. Instead of presenting the three columns above your track listing, a set of columns is instead shown to the left, more akin to a file browser in Finder or Windows Explorer.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

You can choose your preferred column browser layout from the View, Column Browser menu option in iTunes.

Within the column view itself, you can choose to sort by any displayed column simply by clicking on the column heading, and can reorganize the order of displayed columns by dragging and dropping the column headings to the left or the right. Note that the “Name” column must always be displayed at the left. The Album column actually has another trick up its sleeve: clicking on this column heading will toggle between sorting simply by Album, or sorting based on Album by Year or Album by Artist, effectively providing a secondary sorting option to group your albums.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Advanced Track Options

The Options tab allows some additional settings to be modified for your tracks:

The Complete Guide to Album Tagging, Art and Playlists in iTunes
  • Volume Adjustment: This allows you to adjust the volume for the selected track. Volume adjustments are written into a gain tag that is read by iTunes and the iPod, iOS devices and Apple TV. The actual sound of the media file is not modified in any way.
  • Equalizer Preset: This allows you to specify a custom equalizer setting that will be used when playing the selected track in iTunes or on the iPod.
  • Media Kind: This sets the type of media that the track represents. For audio tracks, it can be set to Music, Podcast, iTunes U, Audiobook, or Voice Memo. For video tracks, it can be set to Music Video, Movie, TV Show, Podcast or iTunes U. This determines how the track is shown and handled in iTunes and on your media devices.
  • VoiceOver Language: This sets the preferred VoiceOver language to be used for the track on devices that support VoiceOver such as newer iPod shuffle and iPod nano models.
  • Rating: This allows you to specify a rating for the track. This can also be set on the iPod, iPhone or iPad when listening to the track, as well as set from the normal iTunes media browsing view.
  • Start Time / Stop Time: This allows you to override the start and stop time for the track. The track is not actually trimmed in any way; this value merely applies tags that tell iTunes and your media devices where to start or stop playing the track.
  • Remember playback position: This indicates that iTunes and your media devices should remember your position when you stop listening to a track. It is enabled by default for audiobooks, podcasts, iTunes U content, movies and TV shows, and disabled by default for music and music videos.
  • Skip when shuffling: This indicates that iTunes and your media devices should never play this track automatically when in shuffle mode, whether as part of a playlist or not. This is enabled by default for all non-music tracks. Note that older iPod models such as the fifth-generation iPod will still play these tracks when playing them specifically from a playlist and only skip them when using the global “Shuffle Songs” menu item.
  • Part of a gapless album: This setting is used only by iTunes and the fourth- and fifth-generation iPod nano to disable cross-fade when playing tracks that should be handled as part of a gapless album. iTunes determines automatically if tracks should be played without gaps, and this setting has no bearing on that; it is simply used to disable cross-fade between tracks on those devices that support this feature.

In addition to the tags above that can be set on the Info tab, iTunes also allows additional information to be filled in for video content. The Video tab includes tags specific to videos in iTunes, particularly TV Shows, and allows you to set information such as the TV show name, episode numbers, season number and description. The first four fields apply only to TV Shows, although the Description field is also used by Movies.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

More information on tagging videos can be found in our Complete Guide to Managing iTunes Videos.

Customizing Track Sorting

The Sorting tab provides the ability to override the order in which a given track is sorted within iTunes without changing the actual text which appears for the track. For example, say you have the album 2112 by Rush, but want the album sorted the way it’s spelled out rather than sorted with the rest of the numbers at the bottom of the track listing. You could change the album tag to read “Twenty One Twelve” and the album would sort correctly, but it would also be displayed as such and no self-respecting Rush fan could ever possibly do such a thing. Instead, you could simply enter “Twenty One Twelve” in the Sort Album field and iTunes would sort the album as if the real Album field actually contained that text, while still displaying the correct album name as “2112” in the track information.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

This can be particularly useful for tracks with names, artists or albums that begin with numbers. For whatever reason, back in iTunes 7.3 Apple decided that it would be a good idea to sort numerical titles at the end of the listings, rather than their previous location at the beginning. This allows you to override this behaviour either by sorting these titles phonetically as illustrated above, or simply by prefixing them with the letter A to force them to sort back at the beginning.

Tagging Multiple Tracks

In addition to changing the tags for a single track, you can easily modify the tags for several tracks at once simply by selecting more than one track in iTunes before choosing the Get Info option.

The file information dialog box will show a slightly different layout, displaying the fields that can be applied to all of the selected tracks. Fields that already have the same information in all tracks will be filled in. To change a tag for the selected tracks, simply fill in the appropriate field and ensure the checkbox to the left of the field is selected.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

For whatever reason, some of the fields appear in slightly different places when viewing multiple item information. For instance, the Rating field appears on the “Info” tab instead of on the “Options” tab, and the Part of a Compilation field appears on the “Options” tab instead of the “Info” tab. Options that normally appear as checkboxes are shown instead as drop-down Yes/No menus to make it more clear which setting will actually be applied to the selected tracks.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

The Sorting tab is also available when viewing multiple items, making it simple to override the sort order for an entire artist, album, composer or show. Prior to iTunes 8, setting the sort order for multiple tracks was a considerably more convoluted process involving setting the order for a single track and then re-applying that setting to other similar tracks.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Adding Lyrics to your Music

The Lyrics tab allows you to paste in lyrics for any given track. This is a free-form text field that you can type any information you want into, and some users prefer to fill this in with other information such as extended artist info or information from an album’s liner notes. Keep in mind, however, that this field is set per-track and there is no corresponding field that can be applied to an entire album.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Lyrics can be displayed in iTunes and on recent model iPods and iOS devices. The Apple TV does not provide any support for lyrics, nor do iPod models prior to the fifth-generation iPod or very early iPhone firmware versions.

Numerous utilities also exist for both the Mac and Windows platforms that can display your lyrics while listening to your tracks or search the Internet and add lyrics to your tracks for you. These range from Mac OS X and Yahoo dashboard widgets such as Sing that iTune! (Mac OS X widget:, Windows Yahoo Widget, to full-featured applications such as iTunes Lyrics Importer (Windows, and GimmeSomeTune (Mac OS X, Note that compatibility of these and similar utilities varies with different versions of iTunes, and due to copyright issues there has been a frequent cat-and-mouse game to block access from these utilities to the various online lyrics services they rely upon.

Organizing Compilation Albums

If you have a large iTunes library and you’re concerned about keeping your tracks grouped into proper albums, you’ll likely find that you have several albums with tracks performed by different artists. In iTunes terms, these are called “Compilations” and include albums like movie soundtracks or compilations of music from an era or a theme (ie, “Top Hits of the Eighties”). Since iTunes and the various Apple media devices group your music primarily by artist, this can create a situation where you have a bunch of tracks that aren’t as cleanly organized as they should be. For instance, it’s not uncommon to have one-hit wonders or other obscure artists from these types of albums cluttering up your artist list.

iTunes allows you to mark these albums as “Part of a Compilation” to help identify them more easily and filter out those artists from your normal listings. Note that you also have to tell iTunes and the iPod to actually use this tag as part of its grouping for your tracks, otherwise it’s simply ignored.

To organize your tracks by compilation in iTunes, choose View, Column Browser, Group Compilations. In older versions of iTunes the Group Compilations when Browsing option was found on the “Advanced” tab in your iTunes preferences.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Enabling this option will display a new section, “Compilations” at the top of your Artists listing in the iTunes browser. All of your albums with tracks identified as being part of a compilation are displayed in this section.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Note that if all of the tracks in your library by a particular artist are tagged as part of a compilation, that artist is hidden from the artist listing. This helps filter out the more obscure artists for which you may only have one or two tracks buried on a compilation album. On the other hand, if you have even one other track by the same artist that is NOT marked as being part of a compilation, the artist is still listed separately in your artist listing with all tracks by that artist shown under their name, including those that are marked as part of a compilation.

This behaviour works in the same manner on the iPod classic and third-, fourth- and fifth-generation iPod nano. These iPod models determine whether to group content by compilation based on whether the Compilations menu option is displayed, set under Settings, Music Menu, Compilations. When the Compilations menu option is enabled, the behaviour is the same as in iTunes itself: artists are only shown in the Artists menu if they have at least one song on the iPod that is NOT marked as being part of a compilation, however if the artist is shown, then all tracks by that artist will be shown under the Artist’s name.

iPod models prior to the iPod classic and third-generation iPod nano used a separate “Compilations” setting under the Settings menu. This setting behaves a bit differently from the current behaviour: When enabled, tracks marked as being part of a compilation are never displayed under the Artist name, regardless of whether the artist has other non-compilation tracks on the iPod or not.

Prior to iOS 5 the iPhone, iPod touch and iPad did not support any ability to filter compilations or album artists at all. Although these devices do include a Compilations section, the Artist listing is not filtered—all artists are always shown on the Artists menu, regardless of whether they are part of a compilation or not. iOS 5 adds a new “Group by Album Artist” setting that can be found in the Music settings that works in a similar manner; this setting groups the artist listing and related albums based on the Album Artist information rather than the Artist tag, regardless of whether the tracks are flagged as belonging to part of a compilation or not. A similar “Use Album Artists” setting can be found in iTunes on the View, Column Browser menu.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Not also that the concept of compilations only applies to music tracks, and has no effect in regard to other types of content such as audiobooks, podcasts, movies and TV shows.

Syncing Tag Changes to the iPod

As long as you are using automatic synchronization, any changes made to tags in your iTunes library are automatically synchronized to your iPod, iPhone or iPad during the next sync. Although this technically only requires a change to the device’s content database, the tracks themselves will also be re-copied so that the device contains the latest versions of the actual files with their embedded tags. This can be invaluable for disaster-recovery purposes, as it means that should you ever need to recover content from your iPod without the assistance of the content database, the files themselves will still include enough tag information to rebuild your library.

When managing content on your device manually, however, your iPod, iPhone or iPad is treated as a separate library from your iTunes library, and changes made in one place do not automatically replicate to the other. In this situation, you should either make your tag changes directly on the device itself by selecting the tracks on your device from within iTunes and choosing to edit the file properties from there, or by making the changes in iTunes but being certain to manually re-copy those tracks back to your device when you are finished.

Adding Album Artwork

With the release of the first iPod with a color screen in 2004, Apple also introduced the ability to display album artwork on your iPod and in iTunes alongside your other song information. Today with Apple’s iOS devies and the Apple TV the display of album artwork is an almost compulsory part of the experience. Tracks downloaded from the iTunes Store naturally include album artwork already embedded within them, as will most tracks from other online music services. For tracks you import from your own CDs or other sources, however, you’ll have to go out and fetch the album artwork yourself.

You can view the artwork for a given track either by opening the Get Info dialog for the track and looking at the Artwork tab, or by displaying the artwork panel in the bottom-left corner of your iTunes window, which can be toggled on and off using the fourth button at the bottom of the screen.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Clicking on the title in the artwork panel will toggle between displaying artwork for the currently selected track (“Selected Item”) or for the track that is currently playing (“Now Playing”). If more than one artwork image is available, arrows will appear to the left and right of the title to allow you to view the additional album artwork images for the selected or now playing track. Clicking on the artwork image itself in the artwork panel will open the artwork image in a separate, full-size window.

Adding Artwork Automatically

The good news is that iTunes can assist you with the process of adding artwork to your tracks, at least somewhat. Since the iTunes Store already has a huge catalog of tracks, Apple has chosen to make the artwork from those tracks available to your own music, and can automatically search through your music library, compare it against the iTunes Store catalog, and automatically fill in any missing artwork. There is no cost for this service, although you must have an iTunes Store account to use it.

By default, iTunes will go out and try to fetch album artwork automatically for any new tracks you import as long as you have set up an iTunes Store account. This option can also be enabled or disabled from within your iTunes preferences, under the General section.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

You can also manually tell iTunes to go out and search for missing artwork for any given track on-demand simply by right-clicking on a track and choosing Get Album Artwork from the context menu. Similarly, choosing Get Album Artwork from the Advanced menu in iTunes will initiate a search through your entire library for missing artwork, downloaded and adding any artwork that it finds in the process.

Keep in mind that iTunes won’t be able to fetch artwork for all of your tracks, since it can only find artwork for those tracks that are available on the iTunes Store. Further, it uses information such as song, artist and album name to look up this information, and if the information in your library does not match the information on the iTunes Store, then iTunes will not be able to identify the artwork for those tracks. Further, it’s entirely possible for iTunes to get the artwork wrong, particularly for more obscure albums or albums with more common names (e.g., “Greatest Hits” or “Singles”).

If you find that iTunes has applied incorrect artwork to a track, or want to clear it out for whatever other reason, you can easily do this by right-clicking on the track(s) that you want to clear the artwork for and choosing “Clear Downloaded Artwork” from the context menu. iTunes will prompt you to confirm that you want to do this, noting that only automatically downloaded artwork will be removed, and not artwork that is actually embedded within the file itself.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Like other information about your media files, album artwork images can be stored as tags directly in the media files. iTunes also keeps a cached copy of this stored artwork in its own database to improve performance. Artwork automatically downloaded from the iTunes Store, however does NOT get written to the actual file tags, but is only stored in the iTunes database. This means that if you import these files into another iTunes library or another media management application, the artwork will be missing. In the case of iTunes, this is usually of little concern, since you can easily just fetch the artwork again from the iTunes Store if you’re setting up a new iTunes library. If you’re really concerned about having the artwork embedded in the actual files, however, there are third-party tools such as the Embed Artwork AppleScript available from Doug’s AppleScripts for iTunes.

Adding Artwork Manually

While allowing the iTunes Store to provide album artwork is likely the easiest solution for getting your artwork filled in, it is not a comprehensive solution since it’s likely that at lest some of your tracks will not be available on the iTunes Store. Fortunately, it is fairly simple to add in your own artwork to individual tracks or groups of tracks, either manually or through the use of third-party software.

The simplest way to add artwork to a track or group of tracks is to use the artwork panel itself. Tracks that do not already have artwork assigned to them will display a placeholder instead of the artwork image, noting that you can simply drag in artwork to have it added to these tracks. Drag in a JPG file, or even an image directly from a web browser, and it will be added to the selected track(s). To add artwork to an entire album, simply select all of the tracks in that album and then drag the artwork into the panel in the bottom-right corner. You can also right-click on the artwork panel to paste in an image from the system clipboard.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Note that you can use this method to add artwork to tracks that already contain artwork as well, however the dragged artwork will be added to the selected tracks as secondary artwork, rather than replacing the artwork that is already in the track. Note that secondary artwork images can only be viewed in iTunes—they are not available on the iPod, Apple TV or iOS devices.

If you want to actually replace the existing artwork, the easiest method is to use the multiple file information dialog box. Simply select multiple tracks, choose File, Get Info from the iTunes menu, and then either drag or paste the artwork into the “Artwork” field which appears here. Note that you cannot right-click on the artwork field, but you can highlight it and use the CMD-V (Mac) or CTRL-V (Windows) keyboard shortcuts to paste in new artwork.

Artwork added in this manner will replace any existing artwork in the selected tracks.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

This same method can be used to remove artwork from selected tracks. Simply check off the Artwork field without actually pasting in any new artwork, and iTunes will remove all existing artwork from the selected tracks. Unlike the Clear Downloaded Artwork this method removes embedded artwork as well as automatically downloaded artwork.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Alternatively, you can modify the artwork for a specific track by opening the properties for that track and selecting the Artwork tab. The images contained in the selected track will be shown, along with a slider to zoom in or out on the images, and buttons to either add additional images or delete existing ones. The Add button will open the file browser to allow you to add an image from a file; it does not offer the ability to paste images in from the clipboard or via drag-and-drop. This does, however, provide an alternative method to remove artwork from a specific track before adding in a new image using the artwork panel in the main window.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

All artwork that you add manually is actually embedded in your media files, providing the file format supports tags, as well as being cached in your iTunes library database.

Note that album artwork is not just used for music. All other content types support album artwork as well, including audiobooks, podcasts, movies and TV shows. iTunes does not provide the ability to automatically download artwork for types of content other than music, however, regardless of whether the selected content is also on the iTunes Store. For non-music content, you will need to add artwork manually.

As with adding lyrics, a number of third-party utilities are also available to scour the Internet and add artwork to your tracks automatically. Most of the better tools for this purpose are commercial and must be purchased separately, but can be useful for those with large iTunes libraries who want to ensure their artwork is as complete as possible. A couple of possibilities to check out include iArt (Windows, $10, and Cover Scout (Mac, $30,

Syncing Album Artwork to your iPod, iPhone or iPad

Although previous versions of iTunes provided the ability to choose whether or not artwork was synced to and displayed on your iPod, this option was removed in iTunes 9—artwork from your iTunes library is always synced to your iPod, and there is no way to disable this other than removing the artwork from the iTunes library itself.

At least partly for performance reasons, the iPod and iOS devices do not actually read the file tags themselves to display your artwork. Instead, iTunes creates pre-sized bitmap images of your album artwork to store on your device, and places this in a separate artwork database which is read by the device. The artwork embedded in your media files is completely ignored by these devices.

While this approach normally means that artwork can be loaded much more quickly, particularly on older Click Wheel iPod models that do not have the processing power of a handheld computer, it also means that it is possible for this artwork database to become corrupted or out-of-sync with the rest of your iPod music library. In this case, you will sometimes find that either artwork for a given track is not shown at all, or the incorrect artwork is shown. With previous versions of iTunes, this could be fixed on Click Wheel iPod models simply by disabling and re-enabling the option to sync artwork, however with recent versions of iTunes you will instead need to remove and re-transfer the content to refresh the artwork images. If the problem is widespread on your device, it may be simpler to just Restore the iPod and reload your content from iTunes. The good news, however, is that with recent versions of iTunes and newer iPod models, this issue seems to occur a lot less frequently than it has in the past, especially if you are only using iTunes to manage the content on your device rather than third-party PC or Mac iPod utilities.

As with managing other tags, if you are managing the content on your device manually, artwork changes made in iTunes will not be transferred to the device. You will either need to add the artwork directly to files on the device itself through iTunes, or re-transfer any tracks with updated artwork manually back to your device.

Using Playlists

iTunes offers a very comprehensive set of playlist options for grouping your favorite tracks together, either just for listening to them or as a means to choose which tracks get synchronized to your iPhone, iPod or iPad. These options range from the simple standard playlist that you create and add tracks to manually to the more advanced Smart Playlists and Genius Playlists that can select content from your library automatically based on your listening preferences. Playlists can contain any type of media content from your iTunes library, and can also be grouped into folders.

Standard Playlists

The simplest type of playlist in iTunes is the basic standard playlist. These playlists contain content that you have specifically added to them, and are sorted and organized manually. There are several ways to create a normal playlist: You can choose New Playlist from the File menu in iTunes or click the Plus button found in the bottom-left corner of the iTunes window to create an empty playlist. Alternatively, you can highlight a set of tracks and create a new playlist containing those tracks by choosing New Playlist from Selection from the File menu.

Once you’ve created a playlist, adding additional tracks is simply a matter of dragging-and-dropping those tracks from elsewhere in your iTunes library into the playlist. You can also drag a genre, artist or album directly from the column browser onto a playlist to add all of the tracks in that selection. iTunes will detect if you’re adding duplicate tracks to an existing playlist and notify you of this. You can then choose to either skip the duplicates but add the unique tracks, cancel the add operation entirely, or add all of the tracks to the playlist, including the duplicates of the tracks that are already in the playlist.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

To remove content from a playlist, simply select the track(s) you want to remove and hit the DELETE key. This will remove the tracks from the playlist, but not from your iTunes library. If you want to delete a track entirely from your iTunes library from within a playlist, hold down the OPT key (Mac) or SHIFT key (Windows) when pressing the DELETE key, and iTunes will prompt you to remove the track from your iTunes library in addition to removing it from the playlist.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

You can also add a given track or set of tracks to a playlist by right-clicking on the track and choosing the Add to Playlist option from the context menu. A list of all of the playlists in your iTunes library will be displayed in a sub-menu; simply click on a playlist from the sub-menu and the track(s) will be added to that playlist.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

A Show in Playlist submenu is also available which will display the playlists that already contain a given track. Selecting a playlist from this sub-menu will open the chosen playlist with that particular track highlighted.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Smart Playlists

One of the more powerful features in iTunes is the Smart Playlist. Rather than simply creating a static playlist of your favorite tracks, a Smart Playlist is basically a saved search that can automatically select tracks for you based on a number of criteria that you specify. You basically build the conditions of the playlist, and then iTunes uses the tag data within your tracks to dynamically search your iTunes library on-the-fly and fill that playlist with content that meets those conditions.

To create a new Smart Playlist, chose New Smart Playlist from the iTunes File menu. You can also create a new Smart Playlist by holding down the OPT key (Mac) or SHIFT key (Windows) and clicking on the new playlist button in the bottom-left corner of the iTunes window.

A basic Smart Playlist dialog box will be shown allowing you to choose the criteria to build your Smart Playlist.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

As a basic Smart Playlist, you could simply fill in your favorite artist name and let iTunes select all tracks by that artist for you.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

However, you could almost as easily do this with a standard playlist. Where Smart Playlists become much more powerful is in their ability to not only use multiple criteria, but to also use other information that iTunes keeps track of, such as the number of times you’ve played a given track, the last time you listened to a track, and even the last time you skipped a track. iTunes and your various Apple media devices all record this information as you listen to your music and store it in their database, allowing you to build much more sophisticated and useful Smart Playlists.

For instance, let’s suppose you wanted to build a Smart Playlist of all Jazz music that you had not listened to in at least thirty days. You could simply specify that the Genre should contain “Jazz” and then click the plus button to add an additional criteria line and set it to Last Played is not in the last 30 days.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Of course, if you have a really large collection of Jazz, you might want to limit it only to songs you haven’t heard yet. Again, easily done by adding another line of criteria: Plays is 0.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

However, this may still create a playlist that is too large to synchronize to the average iPhone, so perhaps you want to limit it to a certain size? This is where the Limit to option can be particularly useful.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

The Limit to option can select a limited amount of content based on size in megabytes or gigabtyes, number of items, or play time in either minutes or hours. For example, this could be useful to create a timed mix for a workout:

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Note the use of Playlist is Workout Mix in the above example. This shows how a Smart Playlist can be based on content from an existing normal playlist or Smart Playlist. In this case, the “Workout Mix” playlist would contain a larger list of tracks that are appropriate for working out to, and the Smart Playlist would simply select the least-recently-played 30 minutes worth. If you wanted to get more sophisticated and had put some appropriate information into the BPM field, you could select a good workout mix based on automatically choosing some upbeat music.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Although the BPM field is not populated automatically, there are several third-party tools such as MixMeister BPM analyzer ( that can be used to analyze your library and fill this information in for you automatically.

iTunes 9 also introduced an important enhancement for creating more sophisticated Smart Playlists based on mixed criteria. In older versions of iTunes it was not possible to create a single Smart Playlist that mixed both AND and OR criteria in the same list. For example, if you wanted a Smart Playlist that selected music from more than one genre (ie, Rock OR Pop) that was high rated and you hadn’t listened to recently, you actually had to build two separate Smart Playlists: One to select the content from Rock OR Pop, and then a second one to select the first Smart Playlist and apply the other criteria to it. Thankfully, as of iTunes 9 you no longer need to jump through such hoops and clutter up your library with needless intermediate playlists. You can now create criteria groups to accomplish the same thing in a single playlist. To do this, simply use the ellipsis button (…) to add an additional criteria group, which can be set to match ANY or ALL of the rules in the sub-group.

The ellipsis button for adding a condition group initially appeared as a third button, but as of iTunes 10.4 it is now “hidden” behind the plus button—hold down the OPT key (Mac) or SHIFT key (Windows) and the plus button will change to an ellipsis, which you can then click to add a condition group.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

This example would select all tracks that have not been played in the past two weeks with a rating of greater than three stars and a genre tag containing either Rock OR Pop. The Smart Playlist would be further limited to only 1 hour of music, selected randomly.

As you can see, there are extensive possibilities for some very creative Smart Playlists. These can be particularly useful for keeping your content fresh if you have a very large iTunes library and a smaller iPod or iOS device. Simply create some Smart Playlists that use criteria such as rating, play count and last played for your favorite genres or artists, limit those playlists by size or length and then choose to sync those playlists to your device. As you listen to the music on your iPod, information such as play count and last played date are tracked on the device and when you next sync with your iTunes library, any tracks that no longer meet the Smart Playlist criteria are automatically removed from your device and replaced with fresh tracks that you haven’t listened to recently.

iTunes provides an extensive list of criteria you can use to build your Smart Playlists, including many of the tags we’ve already discussed, as well as other information that iTunes tracks such as dates added, modified, last played or last skipped, counts on number of times played or skipped, and even which playlist a given track is contained in.

The Complete Guide to Album Tagging, Art and Playlists in iTunes

Note that older iPod models released prior to 2007 do not track skip count and last skipped date, so these criteria may be less useful to you if you’re using one of these older devices.

In theory, Smart Playlists should also dynamically update on your iPod, iPhone, iPad or Apple TV wherever possible, although this behaviour has been at least partially broken on iOS devices since iOS 3.1. Further, not all criteria in a Smart Playlist may be available on the device. For example, if you’re basing a Smart Playlist on another existing playlist, that playlist must also be synced to the device.

By Jesse Hollington Senior Editor
Jesse Hollington was a Senior Editor at iLounge. He's written about Apple technology for nearly a decade and had been covering the industry since the early days of iLounge. In his role at iLounge, he provided daily news coverage, wrote and edited features and reviews, and was responsible for the overall quality of the site's content.