I wasn't challenged, but I'll do you one better anyway.
I just found a new feature on my Windows media player that lets me see how many times a given song has been played on my computer. So I sorted my library by this, so I could see the songs that had been played most. Here's a list of my top artists, based on the first song of their's that appears when songs are sorted this way. I did it this way because all my top songs are Guster or Jimmy Buffett just because I have so much more by them, and pretty much the top half of my played list is a mix-and-match of these names. These are just the top song by each.

1. Guster (Either Way)
2. Paul Simon (You Can Call Me Al)
3. Jimmy Buffett (Tryin' to Reason With the Hurricane Season)
Billy Joel (The Longest Time)
4. Black Eyed Peas (The Apl Song)
5. Brooks & Dunn (We'll Burn That Bridge)
6. Jerry Jeff Walker (Viva Luchenbach)
Ray Charles (Busted)
7. Elton John (Daniel)
The Beatles (Yesterday)
8. Johnny Cash (I Walk the Line)
Bob James Trio (Jody Grind)
Athaneum (Different Situation)
9. Marvin Gaye (Too Busy Thinking About My Baby)
10. Everclear (Normal Like You)