Smart playlists

You want to choose Genre CONTAINS Jazz (for example)
The select the check box before LIMIT TO 200 (or whatever) songs selected by RANDOM.

Now, if this is how you have it picked, random may very well include multiple songs by the same artist. It's random. No way to really set that.

If you choose 'least played' . . . or not played within last however many days, you might get a better mix, and hear songs you've not heard before, or in a while . . . you also might find this sight helpful in randomizing your music, as well: www.smartplaylists.com

Good luck!

There's a difference between sorting and selectivity.

You can sort any playlist by anything, by simply clicking the column header of the playlist.

You can make a smart playlist selective by telling it to limit itself to some amount of songs, sorted by X. This sorts the list before it marks the cutoff point, it doesn't control the final sorting of the list.

So if you have it set to pick 5 songs sorted by Random, then it picks 5 random songs. But you can later sort those 5 random songs by artist or anything else.

See the difference?

Turn on shuffle. It's the button in the lower right corner that looks like two arrows crossed, kinda in the form of an X. This will remain set on a per playlist basis.