I have a number of smart playlists but, after a month or so, they get stale. Is there any way to get them to refresh periodically and automatically with all new songs that fit the playlist criteria?

We don’t know of any way to do so automatically, but it’s easy to do so manually. Just select all the tracks in a playlist – click one track, then press Command-A – and press the Delete key. These tracks will be removed from the playlist, and iTunes will repopulate it using the conditions you set for it.

However, perhaps you want to use live updating, so playlists change as you play them. If you select the Live updating option in the smart playlist window, iTunes will constantly update the playlist according to the tracks’ metadata. You’d use this for playlists that have a ‘Plays’ or ‘Last Played’ condition; it doesn’t work for metadata that doesn’t change, such as artist, genre and so on. For example, you might want to create a playlist of songs by a certain artist, but only those you haven’t listened to in the past month.

The Live Updating checkbox tells iTunes to update this smart playlist every time a song’s Last Played date changes

When making a smart playlist, there’s a big difference between choosing Any or All at the top of the window

The upper of the two screen shots above shows a smart playlist for music by Bob Dylan. This playlist looks for tracks that haven’t been listened to in the past three months. Every time a track is played, it gets removed from the playlist and another song is added.

Is it possible to create a smart playlist using music from several playlists? I tried, and it would only work if I added just one playlist. As soon as I add a second it doesn’t work.

This is possible, and you probably got snagged by a little option that often trips people up. Set up your smart playlist where Playlist Is name of playlist, then click the plus (+) icon to the right of that line to add another line. Do the same thing for the second playlist, but make sure you’ve selected the little pop-up menu at the top of the window, so it reads ‘Match any of the following rules’. If you don’t, it will match all of the rules, and will look for songs in both playlists, rather than either one.

When I print a playlist from iTunes, the name of the song is always in the first column, the album second and the artist third. I produce a radio show and have to record each song, and if the artist is in the first column, it would save me a lot of writing if I could print out my playlists in the order I have to record. Do you know a way of doing this?

iTunes’ print options are limited, but you can print out lists of music in another way. Set up the music you want in a playlist, and drag the columns into the order you want. Hide any columns you don’t want to see (press Command-J to open the View Options window and untick the column you want to hide.)

Now select all the tracks and press Command-C. Switch to a spreadsheet program like Numbers or Excel, create a new spreadsheet, then press Command-V; this will paste the tags from the playlist, and you can then print out the text. You can also paste the text into a text editor, and it will show up with one track per line. Not all will accept the text correctly, though. If you use Apple’s TextEdit, Command-V pastes the music files, so you may need to try a few different applications to find the one that works for you.