Ask the iTunes Guy: Prep your songs for other devices

laptop user

With summer just around the corner, I’ve been getting a lot of questions about taking music from iTunes and playing it in other devices. I address two of those in this week’s column, one about burning CDs with tracks in random order, and another about putting a shuffled playlist on an SD card. I also look at how to listen to audiobooks on an iPod shuffle, and a problem where an artist’s name may show up twice in iTunes or on an iOS device.

Burning CDs with shuffled tracks

Q: I have a very long playlist created from a number of CDs. I would like to randomly mix all 500 tracks and then burn a new set of six CDs in random order. I don’t want to have to drag the tracks around in the playlist to change the order; I just want iTunes to mix them up for me. Is there an easy way to do this?

In previous versions of iTunes, when you clicked the Shuffle button above a playlist, iTunes would mix up the tracks and you would see them in a new order. This changed with iTunes 12: iTunes skips around in a playlist to play songs in shuffle mode, rather than showing you the order in which you’ll hear them.

Nevertheless, there is a way to do what you want. You already have a standard playlist with the songs you want to mix up. Let’s call that Playlist 1.

Next, make a new smart playlist with the condition Playlist is Playlist 1. Below that condition, check the box to limit it to a number of tracks. Enter the number of tracks in Playlist 1 in that box. From the “selected by” menu, choose Random. The playlist should look like this:

random playlist

This smart playlist takes all the songs from a standard playlist and mixes them up in random order.

You can now burn CDs from the smart playlist.

Can’t shuffle an SD card

Q: I want to create a playlist with 20 albums and put it on a micro SD card to use on a portable speaker. How do I put the music on the SD card in shuffle mode? I don’t have the option on the speaker to choose shuffle.

It’s the playback device that chooses the order of the tracks. No matter how you put the tracks on the SD card, they’ll generally play in alphabetical order.

This said, there is a way to do what you want. Most devices that use SD cards can read from an .m3u playlist. Doug Adams’ $5 M3Unify can shuffle tracks, and then export copies of the files, renaming the files using a [play order] prefix. This allows you to saved a shuffled group of tracks to the SD card.

Duplicate artists

Q: I’ve got some artists that show up twice in iTunes and on my iPhone. Each one contains different songs and albums. What did I do wrong?

This is a pretty common problem and one that’s easy to solve. I’ve made a screenshot to show what it looks like.

duplicate artists in iTunes

Here you can see that one artist appears twice.

As you can see, there are two entries for Bill Frisell. This is because one of the artist’s names contains a trailing space. Since that space is at the end of the name, you can’t see it in any list in iTunes, or on an iOS device.

To fix this, select all the tracks by one of the duplicate artists and press Command-I. In the Info window, click to the right of the artist’s name in the Artist field. If there’s an extra space, you’ll see that the text cursor is one space to the right of the name. Press Delete to remove the space, and then click OK. Your artist’s albums will all be grouped correctly.

Audiobooks on iPod shuffle

Q: When I import an audiobook to iTunes in order with the CDs numbered and then put it on my iPod shuffle, the tracks are almost always mixed up. I can’t get the tracks in the correct order on the iPod. Can you help me with this?

It’s probably not iTunes that’s the problem, but the iPod shuffle itself. You can listen to the iPod shuffle in two modes: in order, or in shuffle mode.

Here’s a screenshot from Apple’s web page about the shuffle:

ipod shuffle

Use this button to switch between playing tracks in order or in shuffle mode on an iPod shuffle.

Make sure the shuffle button is in the middle to play tracks in order.

Have questions of your own for the iTunes Guy? Send them along for his consideration.

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