I've had great results creating a playlist from iTunes 'Party Shuffle Feature.'
Open 'Party Shuffle' in iTunes and select 100 for upcoming songs. Then COMMAND+A (Select All) and FILE > Create Playlist from Selection
I usually name it Random Music I ... II ... III and so on until I fill that last bit of space on my iPhone.
I've heard some excellent music that I'd forgotten I had using this method!
Open 'Party Shuffle' in iTunes and select 100 for upcoming songs. Then COMMAND+A (Select All) and FILE > Create Playlist from Selection
I usually name it Random Music I ... II ... III and so on until I fill that last bit of space on my iPhone.
I've heard some excellent music that I'd forgotten I had using this method!