Step 1: Read the Pitchfork Media Top 50 Albums of 2006
Step 2: Count the number of albums you’ve listened too and/or own.
Step 3: Count the number of artists you’ve actually heard of.
If you’re like me, the results of this exercise will make you feel incredibly old. I own exactly two albums from this list and have heard of only nine of the artists.
In all seriousness, I don’t really know how to keep up with current music. At least not without spending a lot of money buying all these album’s on recommendation of Pitchfork, or NPR or whomever. Or subscribing to satellite radio which I am loathe to do. And music played on terrestrial radio is either the same classic rock/oldies I’ve heard a million times before, or dreck.
What a pickle!
Panorama of the Mountains 
I actually find it easier to keep up with current music than I did when I was 17 years old in the early 1990s and living in the middle of a cornfield in Michigan. The radio choices were limited to: 1) classic rock, 2) oldies, 3) Top 40, 4) Christian, 5) country, 6) NPR/classical. I had to find out about Jane’s Addiction by going to camp.
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Boston Globe article on resources for discovering new bands.
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