Create a Smart Playlist
You can create a playlist the usual way, song by song, or you can save time with Smart Playlist. Click File, New, then Smart Playlist. When the pop-up appears, choose song criteria: Album, Artist, BPM, Date Added, Genre, Size, and Year, and so on. Then iTunes uses your preferences to create the perfect playlist.
Show or hide the playlist sidebar
If your playlists have vanished from the lefthand sidebar, there’s an easy way to make them reappear. Place your cursor to the right of the Playlists title, and when Show appears, click it. If your playlists are already showing and you want to hide them, then go through the same steps to make Hide appear and then click it.
Guilty-pleasure songs: You love them but don’t want to play them when friends are around, because you’ll never hear the end of it. Just untick those songs so that they never get added to Smart Playlists. Make sure to also tick Match Only Checked Items in the Smart Playlist pop-up window.
Queue your songs in temporary playlists
Playlists and Smart Playlists are great, but if you’d rather DJ on the fly, there’s a feature for that. Go to the song you want to play next, hit Control, and then select Play Next or Add to Up Next. To see your list, click the hamburger icon next to the currently playing track.
Get album art automagically
Your tracks look downright naked without covers. To retrieve album art — for either iTunes purchases or tracks you’ve ripped to iTunes — right-click an album and choose Get Album Artwork. iTunes will more often than not find the appropriate image to insert.
Insert album art manually
If you ripped your CDs but iTunes can’t find the art, then you’ll have to manually add the album covers. Click an album cover and select its entire track list. Then press Command-I. Open Safari and search for the image in Google. Drag the image into the empty cover box under Details, and you’re good to go.
Use comments for personalized searches
Save comments in the Comments field under Album Details — it’s a great way to group songs in a more personalized manner, rather than just by by artist, album, or genre. Just click a song or album, and under Details, type something in the Comments section that’s meaningful to you, such as “summer jams” or “roadtripping music.” Later you can use those search terms to pull up songs for your playlists.
Clean up duplicates
If your library is riddled with song duplicates and you don’t want to spend all day playing search and destroy, there’s an easy fix. Click My Music, then View, then Show Duplicates, and you’ll see all your duplicates on one page, so you can delete them in less time.
Get missing purchases
Not seeing all your purchases? Click Store, then Check for Available Downloads. If there are any, they’ll be added.
Get rid of unplayed tracks
Click My Music, then Songs from the drop-down list at the far right. Then tap Plays to see the songs you play ordered by frequency of play. Delete the ones you’ve listened to least.
Switch to Mini Player
iTunes takes up a lot of screen real estate. If you’d rather see iTunes in miniature, use the keyboard shortcut Shift-Command-M to switch to the Mini Player, which reduces iTunes to the size of a toolbar. Press Shift-Command-M to bring it back to full size.
Control iTunes with your iPhone
If you want to change the current song or setlist but are too lazy to walk all the way to your Mac, iOS apps like BTT Remote give you remote control over your Mac.
Share your music
You can share your music with others on the same Wi-Fi. Go to File, Home Sharing, Turn on Home Sharing, and then enter your Apple ID and password to launch the service. Repeat this on up to five other computers to allow others to stream your library. All they have to do is tap the little house icon on the top left to access your music.
Use iSight to redeem a gift card
It’s a pain trying to type in those tiny, often indecipherable numbers on the back of your iTunes gift card. But there is a far easier way to redeem: Scan those numbers using your Mac’s built-in camera. Click the iTunes Store tab, then Redeem under Music Quicklinks on the top left, and then Use Camera.
Use 2FA for iTunes purchases
Make sure you’re the only person who has access to your iTunes account: Set up 2FA at the Apple ID site. After you sign in with your Apple ID, go to Two-Step Verification under Security Settings. You’ll be asked a couple security questions before setup begins. Once set up, you (and anyone else who tries to access your account) will have to enter an extra verification code sent to your phone before you can buy anything in iTunes.