Organize Your Music and Create Playlists
You’ve got your favorite music in your library, but you’d like to organize it better. In this chapter, I’ll show you how to make playlists, the key to setting up your listening sessions. I’ll look at using tags to create smart playlists automatically with your favorite tunes. I also cover some special topics that will help you with tasks like finding your media files on your disk, managing a large music library, and finding duplicates.
On Playlists
You can listen to your music by album, or by selecting song after song. You can play all the music by a specific artist, or you can shuffle your entire library. But the Music app reveals its biggest strength when you make playlists.
A playlist is a list of songs that you play together, one after the other, with a first song and a last song. Pretty basic; kind of like a CD.
But playlists are more than that. A playlist is a self-contained unit, one with a bunch of tracks you can always play in order or in shuffle mode; a group of songs that you can listen to while dining or when chilling outside; or your favorite lively songs to listen to when you work out.
A playlist can be the equivalent of an album, a double-album set, a live concert, or an opera. It can be a compilation of favorite songs by different groups, or a selection of music for a special occasion. It can even contain all your songs, if you want. With smart playlists, you can create endless playlists that keep adding music as you listen. And a playlist can also include videos from Apple Music.
Let’s distinguish between two types of playlists:
Standard: Standard playlists are groups of songs that you organize manually. The key word here is manually: as you’ll see ahead, smart playlists are automatically created from rules you select, but standard playlists require that you choose every track they contain, and their play order. Standard playlists are also static; they don’t change as you play them, unless you intervene or play them in shuffle mode.
Smart: Smart playlists are dynamic. You choose rules, and Music scans your library for files that match these rules, based on the tags your files contain. (Hence the importance of tagging your media correctly.) In essence, the rules in a smart playlist tell Music to search your library for items that match them.
Create a Standard Playlist
You create a standard playlist by choosing File > New > Playlist, or pressing ⌘-N. Music adds the playlist to the sidebar, and highlights its name. By default, Music names the new playlist Playlist (or, if that name exists, Playlist 2, and so on). Type a name for the playlist, and then press Return to save the name.
It is possible to create multiple playlists with the same name, but try to give your playlists unique names so you can tell them apart. To later change the name of a playlist, find it in the Playlists sidebar, click it, wait a moment, click it again, and type a new name.
Select the new playlist in the sidebar to work with it (Figure 55).
To add items to a playlist, you have two options. The first option has you looking at your Music library as you normally would. When you find an item that you want to add to your playlist, you drag it to the playlist entry in the sidebar. With this way of working, you can’t see what’s in your playlist while you add to it. With the second option, you can see both your library and the contents of your playlist at once.
Drag Items to a Playlist in the Sidebar
You can drag items to a playlist in the sidebar:
Browse your library any way you wish: Albums view, Artists view, Songs view, etc. You can also use the Search field to find items. Drag the items you want to the sidebar and drop them on the new playlist: you can drag songs, albums, artists, or entire genres.
When you’ve finished adding items to the playlist, click it in the sidebar and check that all the right tracks are added.
Open the View Options window (⌘-J) and choose a sort order, such as by Artist, Name, or Year. Or leave the sort order as Playlist Order to either listen in the order in which you’ve added items or to customize the order manually by dragging items up and down in the list.
For more sorting options, choose Songs from the View As pop-up menu. The View Options window expands, and you see your playlist as a simple song list with several columns. You can sort your playlist by any of the visible columns (click a column header to sort), and add other columns by selecting their boxes in the View Options window. If you want to sort the tracks by the order in which you added them to the playlist, you must sort by the item number column; click the unlabeled area that contains a caret above the item numbers to do this.
Drag Items to a Playlist in Its Own Window
You can also open a playlist in its own window and drag items to that window.
Create a new playlist in the sidebar, then Control-click the playlist and choose Open in New Window. Rearrange the main Music window and the playlist’s window so you can see both.
Browse your Music library and drag tracks to the playlist window.
If you wish to sort the playlist, follow the steps described just above.
Close the playlist window when you’ve finished.
Now that you’ve made a playlist, you can edit it at any time. You can also add a description to your playlist: just type where it says Add Description. You can manually add or remove items, move them around, change the sort order, and so on. And if you have an Apple Music account, you can check Publish on profile and in search so other Apple Music users can find and play your playlist. You can see a finished playlist in Figure 56.
To play your playlist, select it in the sidebar and click the Play 
icon on the header bar, click the Play 
button, double-click the first track in the playlist, or click the Shuffle 
button to play the tracks in random order.
About Smart Playlists
While you can make your own playlists by manually choosing which tracks they contain, and the order in which they play, smart playlists can make the process easier. They automatically choose songs, based on your desires. You may never want to use smart playlists, because you listen to your albums only in their original order; or you might want to use nothing but smart playlists, because music, like the universe, should obey other laws than linearity.
Smart playlists act like multi-criteria searches of your Music library, automatically adding items that match rules you choose. Apple used to include a few smart playlists (Figure 57) by default so you could have an idea of what they can do. This is no longer the case with the Music app, but I’ll use Apple’s old examples to show you how smart playlists work. (If you upgrade an existing iTunes library, or turn on Cloud Music Library, you may see these playlists.)
The best way to understand smart playlists is to look at some simple ones to see how they work. To edit a smart playlist (or look at its rules), Control-click it in the sidebar and choose Edit Smart Playlist, or select it and press ⌘-I, or select it and click Edit Rules in the playlist header.
Let’s look at the Recently Played playlist that Apple used to generate automatically in iTunes (Figure 58).
This playlist can be summarized like this:
Match [all media] for [all] of the following rules
[Last Played] [in the last] 2 [weeks]
[Love] [is not] [Disliked]
As you can see in the figure just above, this playlist looks for items that were played in the last 2 weeks. By default, this is “all media,” but you can constrain it by choosing “music” from the first menu. (This means that music videos would be ignored.) It also contains a rule to exclude tracks you’ve “disliked;” see Tell Apple Music What You Don’t Like for more or loving and disliking tracks.
The “Live updating” checkbox is selected, meaning the playlist updates as you listen to songs. As a result, whenever a song in your Music library is played (and, consequently, its Last Played date and time are updated), it is added to the playlist automatically.
With this playlist, you can quickly find the songs that you’ve listened to recently; here “recently” is set to 2 weeks, but you could choose 2 days, 2 months, or some other duration. (If you don’t select “Live updating,” you can play the songs in the playlist as is, but the playlist doesn’t change to reflect anything you’ve played since you created the playlist. To update it, edit the playlist and then click OK.)
There are other smart playlist options. You can select “Limit to” and limit the number of items the playlist contains, its total time, or the amount of data it contains. You can pick its contents by any of a dozen criteria. You can also match only checked items, meaning that unchecked items in your library aren’t added. (I talk about checking tracks in the sidebar The Importance of the Little Checkboxes, ahead.)
The playlist shown above, like the other default smart playlists previously included in iTunes (My Top Rated and Top 25 Most Played) is simple; it uses only two rules. But what if you want more complex criteria? Read on.
Create Smart Playlists
To make a smart playlist, choose File > New > Smart Playlist (⌘-Option-N). By default, the first condition is set up so that its rules match all media, and the first rule is set to [Artist] [contains], with a blank field following.
To begin setting up your playlist, you can:
Choose music from the Match pop-up menu at the top of the dialog if you want to exclude music videos.
Use the first rule that Music offers by typing a name in the blank field to match an artist.
Change the first rule that Music offers by choosing a different tag from the first pop-up menu in the rule. Depending on which tag you pick, you get different options. Choose additional pop-up menu items or fill in the field as needed.
When you type in a text field, Music auto-completes as you type, filling in the closest result to what you’ve typed so far from the contents of your library. If it’s what you want, you can stop typing. If not, keep typing.
You can add either new or nested rules like this:
New rule: Click the plus
button following a rule, and then at the top of the dialog, choose whether an item must satisfy all of the rules you have specified or any of them to be added to the list. For example, you could choose three artists—say Frank Sinatra, Dean Martin, and Sammy Davis Jr.—and have a smart playlist that chooses any one of them (any) or only tracks where all three appear (all).Nested rule: Hold down Option and click the More
button that replaces the plus button following a rule. Within a nested rule group, you then choose whether an item must match all or any of the rules in the group to be included in the playlist.
Below the rules are some important checkboxes:
Limit to: With this option, you can limit your smart playlist. You can choose a duration, a number of items, or a size (in file size); the latter is helpful for creating a playlist to fit on an iOS device with limited capacity. For example, to fill a 64 GB iPhone, make a smart playlist of songs limited to about 45 GB (because you never get the advertised capacity on the iPhone, and you’ll also be using space for apps, photos, videos, and more). In this section you can also tell Music to pick items at random or to include them based on various tags or by when, how often, or how recently they were played.
Match only checked items: Use this checkbox to limit your smart playlist to checked tracks. (I discuss checking and unchecking tracks in the sidebar The Importance of the Little Checkboxes, shortly ahead.)
Live updating: This checkbox tells Music to update the smart playlist every time a change is made in your Music library. Use it for playlists that look at such information as play counts and last played dates, but be aware that if you have a large library and a lot of playlists with live updating set, Music may lag a bit when you make changes to your library.
To make changes to your smart playlist, Control-click (right-click) it in the sidebar and choose Edit Rules or select it in the sidebar and press ⌘-I. You can also Option-click it in the sidebar.
Interesting Things You Can Do with Smart Playlists
The basics of making smart playlists are simple, but you need to figure out which ones will be useful for you. Here are some that I use, which might give you ideas:
Not-recently played music by specific artists: I’m a big fan of Bob Dylan, and I have a playlist of his music that I haven’t listened to in 3 months. Since there’s so much of his music—2,692 tracks, currently—it takes me a while to listen to it all.
In my playlist, I set these rules; the last one is because I didn’t like the Christmas album he released in 2009:
Match [music] for [all] of the following rules [Artist] [is] Bob Dylan [Last Played] [not in the last] 3 [months] [Album] [is not] Christmas in the HeartI limit it to contain 3 hours of music selected at random, and I select the “Live updating” checkbox.
I create similar smart playlists for several of my favorite artists, and even for certain box sets of classical music. For example, I listen to a 21-disc set of Schubert lieder, recorded by Dietrich Fischer-Dieskau, in the same way, though I don’t listen to much classical music in random order.
My 1972 Dark Star playlist: I’m a Grateful Dead fan, and I have dozens of live Dead concerts in my Music library (and hundreds that aren’t in the library). 1972 was a great year, especially for their signature song Dark Star, one of the band’s best jamming vehicles. In the fall of 2011, there was an official release of the band’s entire Europe ’72 tour, with 22 shows, which contain 11 rousing versions of the song. But there are also other officially released live recordings, so I have a total of 16 versions of the song from that year.
I have a playlist set up like this:
Match [music] for [all] of the following rules [Artist] [is] Grateful Dead [Name] [contains] Dark Star [Year] [is] 1972Note that I use
[Name] [contains]Dark Starrather than[Name] [is]Dark Star, because convention is that, when songs segue into each other, one uses > following the title of the song that leads into another song.Whenever I want to choose one of these great versions of this long song, I head to that playlist. Of course, for smart playlists like this, you need to make sure all your music has a correct Year tag.
My super-duper audiobook playlist: In How to Rip an Audiobook CD, I explained how to set up an audiobook playlist for audiobooks you’ve ripped, and keep them in your Music library. I use this a lot, setting up one playlist for each audiobook that I’ve ripped. It makes it easy to listen to audiobooks without having to remember which file I listened to last.
My spot-the-skipped-songs playlist: Whenever you listen to music in shuffle mode, you can skip tracks you don’t feel like listening to, by pressing the Next
icon (or the right arrow key, if Music is the frontmost app). I have a playlist set up with [Skips] [is not]0; this shows me which tracks I’ve skipped. This may tell me about music I’m not that interested in listening to on the go, so I can stop syncing it to my iOS device.The favorite songs playlist: This one is easy: just choose
[Rating] [is greater than] [***], to have 4- or 5-star songs, or[Rating] [is] [*****], to have only 5-star songs in a single playlist. I sync this one to my iOS devices all the time.Studio versus live recordings: I’m a fan of jazz pianists Brad Mehldau and Bill Evans. I have both live and studio recordings from each artist. For the studio recordings, I add studio to the Comments tag and for the live recordings, I add live. Sometimes I want to listen to tighter studio recordings, and other times I want more open-ended live jams. So I have playlists for each.
For example, I have one where
[Artist] [is]Brad Mehldauand[Comments] [contains]studio, another with[Comments] [contains]live, and so on.Mono recordings: I like listening to mono recordings from the early days when stereo was just starting to become common. Back then, producers and engineers spent more time perfecting mono mixes of records than they did the stereo mixes, and I’ve found that many mono albums from this period sound better than the slap-dash stereo mixes. I wrote about this on my blog, in an article entitled In Praise of Mono Recordings.
I have named all my mono albums with (Mono) after the titles, and I created a smart playlist with
[Album] [contains](Mono), which lists all the one-channel recordings in my Music library. Sometimes, when I’m in a mono mood, I’ll head over to that playlist and spin an album by Miles Davis, Bob Dylan, The Beatles, or some classical or jazz recordings from the 1940s or 1950s.Make playlists of artists based on the first letter of their names: If you have lots of artists in your Music library, you may find it annoying to browse the Artists list on iOS devices. One way to get around this is to create smart playlists that gather artists according to the first letter of their names.
To do this, create a smart playlist with the rule
[Artist] [begins with]A, and save it as, say, Artist A. Or, add rules to make a playlist with several initial letters: add[Artist] [begins with]Band[Artist] [begins with]C, and save the playlist as Artists A–C. Make as many or as few as you like, choosing which letters you want each to include. They’ll update automatically as you add more music to your Music library.Find which songs are on your computer, and which are in the cloud: If you use Cloud Music Library, two conditions will allow you to pinpoint the locations of your tracks. You can use
[Location] [is] [on this computer]or[Location] [is] [Cloud]to set up playlists showing which music you have locally, and which you need to download.You can also create a
[Cloud Status]rule that has one of several possible values:[Matched],[Purchased],[Uploaded],[Ineligible],[Removed],[Error],[Duplicate],[Apple Music],[No Longer Available], or[Not Uploaded]. These conditions let you make a smart playlist based on the status of songs in your Cloud Music Library.Find which songs are Apple Music files: If you use Apple Music and download files for offline listening, or if you add music from Apple Music to your music library and the music is still in the cloud, you’ll have Apple Music files. You can find all of them by creating a smart playlist with
[Cloud Status] [is] [Apple Music].
Although the above examples only scratch the surface of what you can do with smart playlists, I hope they give you ideas about how you, too, can make your own.
Organize Playlists
In the sidebar, Music sorts playlists alphabetically in two groups: smart playlists first, then standard playlists. Within either of these groups, you can use some tricks to move certain playlists to the top of the list. I use dashes (-) before playlist names to force Music to put them at the top of the list.
For example, these playlists, because of the dashes, sort in this order:
--Classical Rotation
--New Music
--Other Rotation
-Grateful Dead Europe 1972
-Hot Tuna live
Bob Dylan
Brad MehldauAs you can see above, double-dashes sort before single dashes. This lets me create several levels of sorting within a list of playlists.
You can do more, though: you can use folders to organize playlists. To add a folder, choose File > New > Playlist Folder. Name the folder, and then drag any playlists you want into it. You can show or hide a folder’s contents by clicking its disclosure triangle. Folders display above playlists in the sidebar.
If you have a lot of playlists and a lot of folders, you may want to even use subfolders. Just select a folder, then choose File > New > Playlist Folder to create a folder within the selected folder. And so on. You can have folders all the way down.
Coming back to those dashes, you can also use them to keep folders in a specific order. Playlists that aren’t in folders will display below the last folder, in alphabetical order. However, if you start using folders—if you have enough playlists that it’s necessary—you may find it best to create folders to group all your playlists.
Delete a Playlist
If you want to delete a playlist from your library, select it in the sidebar and then press the Delete key. Music asks if you want to delete the playlist. You can check the “Do not ask me again” box if you don’t want to see this warning again. When you delete the playlist, you lose the structure of the playlist; to get it back, you must rebuild it manually, or re-create the rules for a smart playlist. However, deleting a playlist does not delete the tracks in the playlist from your Music library or computer.
You can delete a folder as well. This deletes all the playlists it contains.
Delete Songs from a Playlist
If you want to delete songs from a standard playlist, but retain the playlist, select a song and press the Delete key. You get an alert, asking you to confirm the deletion. Deleting a song from a playlist removes it from the playlist, but does not delete it from your Music library or your computer.
You can’t delete songs from a smart playlist directly; instead, to change a smart playlist, you change its rules. One exception is in the case of a smart playlist that has the “Limit to” checkbox selected so that its tracks are constrained by a factor such as time or size. If your playlist’s conditions match exceed that limit, deleting one or more tracks from the smart playlist is possible (select the track in the playlist and press the Delete key). When you delete a track in this way, Music adds another track to meet your limit.
Delete Songs from Your Library
When you delete a song from your library, you have two options: you can delete the its entry from the library and still keep the file on your disk, or you can delete both the entry and the file. If you do the latter, make sure you have a backup (though you may not want to back up certain files, such as podcasts you’ve heard and don’t want to keep):
Delete a song from your library: Select it in the library (i.e., not in a playlist) and press Delete. You are asked whether you want to keep the file or not. If you use Cloud Music Library, you’ll be asked if you want to remove the download and still keep the song in your library in the cloud. (If you have a local version of a song that’s stored in Cloud Music Library and want to delete that local song, Control-click the track and choose Remove Download.)
Delete a song from both a playlist and your library at the same time: Select it in a playlist and press ⌘-Option-Delete. You see the usual dialog asking you whether you want to keep the file or not.
Eliminate Duplicates From Your Library
You may have songs on both regular and best-of albums; you may have studio and live versions of songs; or you may have—cough—downloaded songs more than once and added them to your library. The Music app can help you find duplicates, items that have the same name and artist in their metadata. It can also find exact duplicates, which have the same name and artist, and album.
To find duplicates in your entire music library, select an item in the sidebar that contains all your music, such as Artists or Genres. Or, if you want to hunt down duplicates in, say, just a playlist, select that playlist.
Now, choose File > Library > Show Duplicate Items. Music displays a list of songs that meet this duplicate criterion in a list view. Click the Name column header so songs with the same name group together. Some may be real duplicates, such as the same song on an original album and a best-of album. In such cases, you may want to keep only one of these, or you may want to uncheck one, so it doesn’t play or sync. If you have studio and live versions of a song, however, you’ll probably want to keep both. To whittle down your duplicates to show only those on the same album, click Same Album in the Header Bar.
To see exact duplicates—those where the song name, artist, and album are the same—click Done at the bottom of the Music window. Then, hold down Option and choose File > Library > Show Exact Duplicate Items.
When you’ve finished examining your duplicates, you can decide whether you want to delete any of them (see Delete Songs from Your Library). When you’ve finished perusing duplicates, click the Done button at the top of the window to see all your content again.