Shuffling the (newer) Ipod
Five songs at random. And .... go.

Walking on Broken Glass (Annie Lennox)
Why I downloaded it: It's bouncy and catchy, if a little inconsequential.
What I like about it: The video with a somewhat giddy Hugh Laurie, before he was House. A takeoff of Dangerous Liasons, the video also features John Malkovich. The funniest part of the video is Laurie trying to convince party guests than Lennox is plastered. But I still watch Chuck instead of House on Mondays.

Mona Lisas and Mad Hatters (Elton John)
Why I downloaded it: To me, it's simply the best song Sir Elton has ever done.
What I like about it: It's a deeply personal song for me, a song that seems to strike at loneliness, which was a theme of mine when I bought the Honky Chateau CD in 2004. I was driving through unfamiliar towns and meeting unfamiliar people, and missing Bowling Green. The song has plenty of urban references within its beautiful melody, but it still connected with a 23-year old college kid trying to make it in rural America.

Summer in the City (The Lovin' Spoonful)
Why I downloaded it: It's a classic recording, a rare case where odd sound effects enhance the track.
Why I like it: Add the crucial piano track and the intensity brought out in the recording, and it's a must-have. In my mind, best used in Ken Burns' Baseball, used as the backing music for a section on Carl Yastrzemski and the 1967 Red Sox. That was before I hated the Red Sox.

Africa (Toto)
Why I downloaded it: When I was five, when I was 15, when I was 28, still one of my favorite tracks.
Why I like it: The drum beats were great, but I think this is a song I can't compare to anything else on the radio at the time. I never knew much outside radio as a young kid, but this song always made me stop and listen. Don't care one way or the other about other Toto tracks, but this is one I needed.

Classical Gas (Mason Williams)
Why I downloaded it: Almost any task can seem doable with this in the background.
Why I like it: Who doesn't like this? It's too catchy to hate.