I have over 100,000 songs in my iTunes library.
Making playlists is a pain in the ass sometimes
Enter The Filter
http://www.thefilter.com
You highlight one or two songs from your library, and the beast goes to work, creating playlists I'd never conceive of.
I highlighted Bootsy Collins - Shock It To Me and Men At Work - Who Can it Be Now
THe resulting playlist included Prince, The Dandy Warhols, Blondie, Starsailor, Rick James, The Brian Jonestown Massacre, Jimi Hendrix, Rocket From The Crypt, Depeche Mode, Radiohead, KC & The Sunshine Band (a few examples)
The results are sometimes bizarre, but always interesting.
My next playlist is building right now, based upon my selection of Filter and Nina Simone.
Can't wait to hear what happens
Oh... just about forgot to mention.
IT'S FREEWARE!!!
A best practice if you have a large library like mine:
Set Party Shuffle for like 5 songs. Highlight two. Create Playlist. Repeat.