I got tired of hearing the same songs over and over during my train rides, so I wrote an app that plays your songs with no repeats ever until you've heard them all.
I priced it high on the theory that people with lots of music have already put hundreds or thousands of dollars into their music collections and wouldn't mind spending a little to enjoy all their songs in a useful way. I actually tried a free version at one point and it sold the same number of copies as the $4.99 version, so I ditched it and just have the paid version.
EDIT - Don't want to feel spammy here, and wasn't going to include a link to my app, but for those who do want a "listen to all my songs with no repeats" solution, True Shuffle does the job. Hit me up for a promo code if you need one, eh.
iTunes will play all of your songs without repeats until you have heard them all as-is. A user would simply go to their music collection, select the shuffle action, and then begin playing a song. No song will be repeated until all of them have been played, which you should have been able to take away if you read the OP or the comment thread. As for the fact that your app is $5, I will refrain from saying anything besides do not spam the link to it on HN please.
http://itunes.apple.com/app/true-shuffle-pro/id355913111?mt=... , if you're interested.
I priced it high on the theory that people with lots of music have already put hundreds or thousands of dollars into their music collections and wouldn't mind spending a little to enjoy all their songs in a useful way. I actually tried a free version at one point and it sold the same number of copies as the $4.99 version, so I ditched it and just have the paid version.
EDIT - Don't want to feel spammy here, and wasn't going to include a link to my app, but for those who do want a "listen to all my songs with no repeats" solution, True Shuffle does the job. Hit me up for a promo code if you need one, eh.