Musical tastes

So I have this archaic mp3 player which serves my needs for the most part. It holds about 385 songs, which I know is puny, but I'm fine with it.
I have discovered that the "shuffle" option doesn't really work all that well. It tends to play the same 15-20 songs at random.
A solution to this is to "*Play all" under the Tracks selection in the library. I get a random sampling of songs and all of them play. However, they play alphabetically by title.
I have noticed some jarring transitions, due primarily to my ecclectic downloads in this alphabetized list. For example:

Can't Keep it In (Cat Stevens)
Carmina Burana -O Fortuna (Carl Orff)
Cecilia (Simon & Garfunkel)
Cello concerto in E flat major (Antonio Vivaldi)

Que Precio Tiene el Cielo (Mark Anthony)
Red Rooster (Howlin' Wolf)
Regina Coeli (Mozart)
Remembrance Day (Midge Ure)

The one that always gets me is the Carmina Burana to Cecilia jump.