It's a little hard to know exactly what's in your library. Assuming
you used Release Year, how many actual tracks are listed from
different albums ? It's quite possible using a single selection (such
as "before 1940") you might have only those 2 albums matching.

You can bracket a duration by adding multiple criteria, for example,
set one as "Is After 1950", and add a second filter as "Is Before
1960"

You could use Criteria : Randomise if you want them in no particular
sequence.

To do that, add criteria to the existing ones, then scroll to the
bottom of the criteria list, click More... and choose "Randomise
Playback Order" from the extended list.

Supposing you *did* only want 2 tracks from each of 3 albums, you can
then choose Title Is / Contains (album name) and Limit number of items
to 2 as a second criteria. Then, repeat twice using the "And also
include... music in my library" with the other 2 album names.

If you wanted your least played tracks, you could also choose Sort By

As you can see there are lots of possible combinations to get close to
what you're after, though I'm sure there's no one-size-fits-all way to
do this. The filters included seem pretty powerful compared to older
WMP though.

HTH
Cheers - Neil
------------------------------------------------
Digital Media MVP : 2004-2007
http://mvp.support.microsoft.com/mvpfaqs