Wow - how the heck do you do that?

It’s been discussed before and it takes a little bit of time to set up, bet here’s how I’ve got mine set up:

-First you create your "weighted shuffle" playlist and create a single playlist underneath it that has “select X tracks” checked and set to 14 (or whatever number you like. 14 tends to be a solid hour if you don’t skip any songs).
-Copy and paste the new playlist into the “weighted shuffle” playlist a dozen or so times so that it’s repeated about a dozen times.
-Now under the new playlist you just copied create a separate playlist for each artist you like.
-For each artist set the “select 1 track” option so that for each artist that’s selected you’ll only get 1 track at random
-Copy the songs you like into each of the appropriate artist playlists. You can optionally make certain songs come up more often by using similar techniques with sub-playlists at this point.

This has the effect of selecting around a hundred and fifty relatively equally weighted songs. Sometimes you do get two songs by the same artist close together (like the end of one set of 14 and the beginning of the next set), but the more artists you have the more rare this becomes. Even when it does happen, I generally find it’s not undesirable and you don’t here the same artist for at least another 14 songs.

There actually is a way to take this to another level of ridiculousness so as to NEVER get songs by the same artist close together (by making yet another sub level with half of the artists in each) but I’ve found the method outlined above works just fine.

Other people I believe simply create on list with every artist set to select one song per artist, but my method feels more like a “radio station” to me so that’s what I do.