New Favorite Thing in iTunes
The "Genius" playlist. If you click on a particular song, which I'll do as the entirety of my music is on "shuffle," the "genius" will select songs that go along with it for a 25 song playlist. Of course you can modify the song count and you have to let Apple access your iTunes info so it can apply whatever algorithm those clever dicks have cobbled up to your music library. I was reluctant at first to do so as I do like my privacy but I ended up accepting Apple's protestation of respect for the individual's personal info.
In comments, give me a song and if I have it, I'll generate a playlist and list the songs in a later post if you'd like a sample. I'm grooving to Donal Fagen's "Snowbound" right now after listening to Paul Simon, The Pretenders, Joni Mitchell, Joe Jackson. All generated off Fagen's "It's What I Do" from "Morph the Cat."