Shuffling Songs

It totally bugs me now that even when i have "toggle playlist shuffling" set to on on Winamp, that it doesn't exactly shuffle properly. The music i have on winamp is in alphebitical order. At the minute if i've been listening to Dream Theatre, i'll get Dream Theatre as the next song as well. Literally out of just over a day's worth of music, not short of 400 songs, it keeps picking a song very close the the one it's currently playing to play next. Annoying...