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According to my iTune play count the most played track is "Burn-In Tones" from the Sheffield/XLO Test disc. The test disc has 3 of the top 10 most played tracks. The most listened to music is David Baerwald's "Wondering". Other artist in the top 10 played tracks are Dixie Chicks, Amy Winehouse, Seal and Lucinda Williams. Statistics can be a little misleading since my go to track is Bryan Ferry's "The Right Stuff".
Migueca, you nailed it for me but on that album my favs are Private Investigations and Telegraph Road. But other frequent albums are:
David & David-Boomtown
Renaissance-Live at Carnegie Hall (great performance/poor recording)
Roger Waters-Radio K.A.O.S.
Bruce Cockburn-World of Wonders
just to name a few that come to mind