So today I've had three songs so far come on my iPod that make me think of people from my past.
"Michelle" by The Beatles - A girl I was fascinated with in college, and I believe was named for this song. One a related note, my first crush (in second grade) was on a girl named after The Beach Boys song "Barbara Ann".
"Don't Give Up" by Peter Gabriel - My senior year of high school, I got turned down from all of the universities I applied to. I listened to this with my then girl friend, Kim, and the two helped me through it.
The Extremist by Joe Satriani - I wasn't paying enough attention when this came on to track the song title, but the whole album has importance to me. My friend Steve (SecondLife not The Rooster) drove me to my first and only Society for Creative Anachronism (SCA) event in Stockton. He said I could go through his music and choose what to listen to, and I found this album. We left it in and it was the soundtrack for the drive to and from the event. I think this was the point where Steve went from being just an RPG buddy to a full on friend.
There are a lot of other songs that I catch that bring back other memories. Any that were on the radio in early 1984 remind me of Ultima III (which I got for Christmas 1983). Sometimes I'll be in a store and some song will come on over the music system, and I'll turn to Jennifer, and say, "This is an All-Skate." And the music from 1995 to 1997 is embedded in my head from being in grad school.
That's why I love my iPod.