Random order and custom order of an iTunes music playlist

I listen to music almost nightly on my iPod Nano Touch. I’ve been doing that for a while now and one thing bugs me. Not from the songs, but from the sorting options and the shuffle on the iPod. The former has resulted too often in repeat order and the latter is never random enough. In fact, despite shaking options to randomize the shuffle, too often the same songs end up in the first-plays of a shuffle, just with a few different ones around them, and in a different order than the last play. Talk about annoying.

I wanted to jumble a playlist order by a static means – do it before I start using the iPod. Call it a static shuffle that randomly arranged things. The results I kept finding on Google search results were pointing to Apple forums with people asking the same question and the answer being a proverbial shrug with directions simply to employ shuffle to do the job. That’s frustrating.

Last night, though, I did something random on iTunes, just a shot in the dark attempt. Maybe I already have crossed this option in the past and done the deed and I had just forgotten. Maybe it’s already widely known as well as posted online on another instruction-attempt article/blog post (or several dozens of them), but there is indeed a means to randomize a playlist (with the program doing the first bit of work and you gaining the liberty to do the rest).

Note: This was done with iTunes version 12.7.14. If it works with later versions, grand. I’m certain it works with earlier versions of the software too.

1. Open iTunes
2. Select a playlist that you want to jumble/randomly arrange.
3. Look at the list sorting options at the top of the list (things like name, play count, last played – they are fields that you have had the ability to randomly set).
4. On the far left side, there will be no option above the numeric ordering column. Click on that sort area.

What should happen is there will be a re-sort – call it a jumble – of the playlist order. The most important thing is here that you now have the ability to randomly sort the song list order; highlight a song on the list and drag it up or down to the position you want it in the order.

You won’t get a jumble-sort again by clicking the number-sort field over and over again. It’d be a plus if users did get that. There’s no guarantee a static, visible playlist order shuffle is going to be truly random (just as I complained the Nano shuffle was not random enough), but having the manual ordering ability is a plus that will likely be more beneficial to short playlists than the long ones. The latter would take a lot more time to get just right, with no guarantee you ever make it through the entire list.