A little ways into the list I posted a comment where I thought I noticed a pattern in these. Songs played the most tend to fall into three categories:
1. I have had them on my iPod for a very long time.
2. They show up on multiple preset playlists of mine.
3. Short songs are more likely to be higher on the list simply because my iPod doesn't add a "play" to the play counter unless a song is played in its entirety -- and I'm more likely to cut off a longer song before the end (especially when I am playing it on the road and I reach my destination).
Oh, and where’s Santana? :)