I have my entire music collection queued up in WMP10, and it plays the same ~40 songs out of ~2100 over and over and over...
My solution:
C++
class playlistItem {
public:
string m_songTitle;
int m_songLength; // In seconds
// Other member functions/variables left out for simplicity
};
int playlistLength = 0;
playlistItem myPlaylist[];
// Initialize the list here by reading the music directory //
// Also set the value of playlistLength according to the //
// number of subscripts in the array. //
// Pick a random subscript from the array //
srand(rand()); // Seed the random number generator
int playThisSong = rand() % playlistLength;
playlistItem randomSong = myPlaylist[playThisSong];
// Play the song! //
randomSong.play();