I like doing this every now and then. Take your music library/ipod/zune/etc put it on shuffle and list the first 5 songs that come up.
1) Billy Holiday - I'll Get By
2) Silver Jews - Aloyisius, Bluegrass Drummer
3) Erykah Badu - Reprise
4) David Bowie - Suffragette City
5) Nine Inch Nails - Complications