Thank you! This was exactly what I was looking for. I use this to transfer random 5-star songs to my Clie everyday. It wasn't refreshing, but I just didn't realize you could hit delete.

Glad to help!

I don't have a randomize button. Is this an apple-only feature of iTunes?

I find the static random assignments one of the most annoying problems with iTunes. Is there a hidden button that will solve all my problems?

Dave,

The randomize button on Windows is the shuffle button. To re-shuffle shift-click on the shuffle button.

To see the change as you make it, make sure you have the playlist sorted by track number.

Shuffle works fine. Random selection does not. I assume that this is why the method of selecting by "least recenly played" is favored by so many people here.

If you play your iPOD on shuffle a lot, then over time the "least recently played" selection method converges to a true random selection method (at least insofar as shuffle is truly random).

As far as I can tell turning shuffle on and off has no impact on the problem with the static selection of random songs. For example, I have a smart playlist called "Test 1 5-star".

The criteria for "Test 1-5 star" are:

My Rating is *****
Limit to 1 song selected at random
Live Updating

On my iPOD, the song that is selected is The Jam's "That's Entertainment". That never changes. I could add criteria to say I didn't want anything played in the last 7 days, but then after 7 days, "That's Entertainment" would be back on top.

I assume that when a song is added, iTunes must assign it a random number, but once it's assigned, it's fixed. This type of static randomization is almost completely useless.

Does anyone know if Apple considers this to be a bug, and if they do, is there any common terminology they use when they talk about it?