I love this feature! With over 4,000 songs on my iPod ranging from classical to jazz to classic rock to rap/hip hop to metal to blues to musicals to stand up comedy to movie music, etc., I just never know what's coming next. Sometimes it's surprisingly funny (example, Jimi Hendrix ending one song, introducing another, and then having an Abbott & Costello routine then follow) and sometimes just cool (hearing a song I haven't heard in ages).
Love putting the iPod on shuffle for my morning and evening dog walks. Awesome feature!