I love listening to music, all different types. For the last couple years I have been in a bit of a lull listening to the same thing because I don't know what else to pick. We previously loaded our entire CD collection onto our computer so our music is all in one place but it almost became too much all together. I couldn't just open iTunes and put it on random because I would always end up with some rap or death metal or Christmas music coming on. I've thought (and mentioned) many times that the best gift would be if someone would just make me a couple of playlists of the songs that I like and maybe add some new songs in there too. It hasn't happened and I just don't have the time to sit and make one of my own without just picking the same few songs I always listen to. Now I discovered something awesome recently, exactly what I was looking for. iTunes has a new (I think) feature called Genius. Basically you choose one song from your library and it will make a playlist for you. It will even suggest some new songs that you may like. You can then just listen to it, or save the playlist or refresh it if you're not happy with what you got the first time. I love it! So far I've had good luck with it and rediscovered some music in my collection that I had forgotten about.
Here are a few of the songs I've used to make playlists lately:
"If You Want to Sing Out, Sing Out" Cat Stevens
"California Stars" Billy Bragg & Wilco
"Anywhere from Here" Polly Paulusma
"Only in the Past" The Be Good Tanyas