Do the iPod shuffle!
Once you get a significant number of songs onto your iPod (bear with me, it's a new toy and I will be talking about it a lot), the "Shuffle" function acts almost like a mini radio station, but with some really far ranging options (e.g. Jazz, Bluegrass, Hip Hop/R&B). Here's the last six songs I heard on my iPod:
"I'm Just A Killer For Your Love" - Blur
"Batman Theme Reprise" - Danny Elfman
"Venus De Milo" - Miles Davis
"Keep On The Sunny Side" - The Whites
"Tape You" - N*E*R*D
"The Phantom of the Opera" - Michael Crawford and Sarah Brightman