STYLETHREAD -- LET'S TALK SHOP!

i have noticed this...and i kind of assumed it was because i used to always let it start on the first song, now i start playing a song in the middle of my playlist (just scroll down and click without paying much attention) and it seems to be a bit better.

there is an setting in your iTunes preferences, i would assume it transfers to the iPod, but you know, it might not...anyway, it's called Smart Shuffle and it at least decreases the likelihood of hearing the same artist/album in succession, which is part of the problem talked about in that article Maddie posted.

in iTunes, it's under the Edit menu > Preferences > Playback tab...there's also a choice to shuffle songs, albums, or "groupings" and i'm not sure what that part does.  maybe worth an experiment though?