If you go looking for a solution to this problem, one of the first things you’ll come up with is the Skip when Shuffling option in iTunes. This allows you to mark which songs should be omitted when you’re using the Shuffle Songs option. Bizarrely though, there is no way to apply this setting to multiple files at once. So if you have a couple hundred files or more that you’d like to apply this to… well, you get the picture I hope.

The solution I’ve finally settled on is a little less than perfect, but it works. It involves putting a unique comment into each of the songs that you’d normally like to be skipped when shuffling, then creating a smart playlist to skip just those songs. And here’s how you do it:

1. Fire up iTunes and start selecting the songs you’d like to skip.
   You don’t have to select them all at once; just do it in batches, i.e.: select whole albums or sort by genre and select all the Jazz songs for example.
2. Right-click (Ctrl-Click on the Mac) one of the selected songs and choose Get Info.
   At this point, iTunes might warn you that you’re about to edit multiple files at once… that’s fine; that’s just what we want to do.
3. On the Info tab, add the text “noshuffle” (without the quotes) to the comments text box.
4. Click OK, and all the selected songs will be updated.
5. Repeat the steps until you’ve done this for all the files to be skipped.
6. Create a new smart playlist
   File > New Smart Playlist…
7. Set up a new rule where “Comment” “does not contain”, then enter “noshuffle” (again without the quotes) into the text box.
8. Make sure the Live Updating check box is ticked, then click OK.
9. Give your new playlist a descriptive name like “Shuffle”.
   
10. Sync the updates to your iPod.
    

The playlist will now appear in the list of playlists on your iPod. We’ve still not shuffled this new playlist though. Once again, Apple could have made our lives a whole lot easier by adding a shuffle option to the New Smart Playlist dialogue. For now though, before playing your new playlist, make sure you set the Shuffle option under Settings to “Songs”.

Whenever you add new music to your library, make sure you add the “noshuffle” comment if you want the files to be skipped when shuffling, and iTunes will automatically update your playlist.

An alternative to putting a “noshuffle” comment into each of your files, is to give all of them a rating of 1 star and then setting up your smart playlist to ignore songs with a 1 star rating.

Of course the big drawback to this solution is that you keep having to turn the shuffle on and off from the settings menu (why does the iPod have no option to turn on shuffling during playback?), but it works for me, for now. If you have a better solution, let me know!

Some Sony car stereos (such as mine) have a Unilink system, which is used for connecting up auxiliary devices such as CD shuttles. The Unilink system consists of standard RCA (component) inputs (picture 1, below), and a proprietary Unilink input (a round, black plug - pictures 2 and 3). Therefore, to hook up an auxiliary device to your car stereo, you would need to connect it to both the component and Unilink inputs. A bit of a problem for us if we want to hook up our iPod. We’d want to connect the iPod to the component inputs, but what do we do about the Unilink connector?

So I did what any normal person would do in this situation… I googled. I quickly found an excellent article entitled Connecting the iPod to Your Sony Car Stereo. The author details a number of methods to get your iPod playing through your car stereo, including:

• FM transmitters and modulators
• Cassette adapters
• A few relatively expensive solutions offered by Sony
• And a few “hacky” solutions, which didn’t really appeal to me

In fact, none of the solutions offered in the article seemed like a good fit for me, although I urge you to check it out for yourself… There are some very complete and integrated solutions there that will probably satisfy most people. I don’t like spending a lot of money, and I don’t really like taking the hacker approach.

I googled some more and came across this little gem: An Autoleads PC7-100 Aux Input Adapter for Sony car stereos — the link is to a UK based site (I have no affiliation, but it’s the cheapest I could find at £25). Feel free to search for it your own area though, although at the time of writing, I think it’s only available in the UK. It’s basically a one-ended lead that connects to your Unilink input and fools the car stereo into thinking that a CD shuttle is attached.

Then all you have to do is run a lead (mini stereo jack to RCA) from the component inputs on the back of the car stereo to the cabin of the car, plug in your iPod, select the CD or source button on your stereo, and that’s it!

Additional resources

You may find the following links useful:

Connecting the iPod to your Sony Car Stereo
Sony Unilink to iPod Hookup