I’m a music obsessive with over 200GBs of MP3s in my iTunes library. I use a 16GB iPhone and had been loading it principally with my ‘New’ finds and stuck with a few ‘No Deletes,’ leading to a selection of music that rarely suited my moods and provided very few safe old favorites. All too often, I found myself flummoxed by carrying hundreds of records, but totally sick of everything I had on it.
Shuffle play has its place, but I still love to listen to albums start to finish, letting the artist present their music in their own context. After playing around a bit last week with Smart Playlists, I’m pleased to offer this post on filling your iPod/iPhone with random albums. Doing this has brought up a lot of forgotten favorites and released space on my portable device from newer albums that I liked, was tired of but couldn’t bring myself to delete. It’s entirely refreshed my whole portable listening experience by digging out records I haven’t thought about in years.
Here is an easy step-by-step for getting it done:
1) In the Control Menu, set Shuffle to “by Album”

2) Create a new Playlist Folder for your iPod or iPhone. (For the rest of this post, I’m just going to call it an iPod, OK?)

3) Create a regular Playlist for your “Musts,” the albums that you still feel like you absolutely must have handy – or perhaps albums you’ve recently acquired.

4) Drag your Musts into that list and note at the bottom of the iTunes screen how much hard drive space they take up.
5) This is the critical step. Create a Smart Playlist. Use the three setting shown in the illustration below:Artist contains [press Space Bar once], Media Kind is Music (to keep out pesky Audiobooks and Podcasts) and Playlist is not [the name of your Musts Playlist], which prevents duplicates. Use the “Limit” line at the bottom to be however many GBs are remaining on your iPod after you subtract the amount of space reserved for your Musts from Step 4 plus anything else you keep on your iPod (Podcasts, Photos, Videos, etc). You can add on more lines to fine-tune it for your needs by adding lines like “Last Played is more than 90 days ago,” excluding certain artists or genres, or whatever you fancy.

6) Now plug in your iPod and select it from the left sidebar. On the Music tab, select Sync Music: Selected Playlists and deselect the “Automatically fill free space with songs” button. Down below select the Folder that has your Musts and Random playlists.

7) Sync and be happily surprised next time you’re out & about with your iPod.
You likely wound up with a few dud albums on your Random Smart Playlist. Use the Grid View to delete it. The list will automatically refill to your level of GBs. Sync again and you’re set.
An important note about maintaining your Random Smart Playlist: Because you are filling with Albums to some level of GBs, you will inevitably have an incomplete album at the bottom of the playlist. My suggestion is tonever sort the random playlist in List View. That way you can always go into List View to delete those fragments from the bottom of the list. If you don’t do this, after refilling your Random Playlist you will wind up with a number of incomplete albums, obviously an undesirable situation. Of course you can always Go Nuclear and delete everything in your Random Smart Playlist to refill from scratch, too. Happy listening!