My Funny Valentine (Chet Baker)

Chet Baker is the progenitor of heroin chic. A distinctive - though consistently low-key - trumpeter, Chet left his most lasting impact with his paper-thin, but always compelling, vocals. This is his take on one of the greatest songs of the American songbook. Let's get lost.

Columbus Stockade Blues (Doc Watson)

Old Guy Clark sang, "I have seen The David and the Mona Lisa too, and I have heard Doc Watson play the Columbus Stockade Blues." Born on this day in 1923, the great Doc Watson.

There's a Wall in Washington (Iris DeMent)

Somehow I missed Memorial Day - or Decoration Day as it was known in the old South - even though I posted about my grandfather and World War I. Here is my favorite - respectful and bitter - song about those who gave their lives for our nation. This song betrays my youth and the sense of futility we all felt about "America's longest war."

Tired of Being Alone (The Reverend Al Green)

I thought of my friend, Hope Kurtz, today. In 1985, I was a neighbor of her and her husband Steve Kurtz while we were all in graduate school in Tallahassee. We were all very different people from very different backgrounds - but in spite of it all, we found a way to become great friends. Steve taught me about punk and post-punk music - a decade I had missed altogether. Hope loved soul music and would come over mid-morning and we would listen to her favorite artist, the Reverend Al Green. Our visits were purely platonic and were only about the music. Hope died much too young in 2004. I do not know how many times since then that I have stopped mid-morning and played Al Green and thought fondly of Hope. I love you Hope - and Steve. RIP.

Dublin Blues (Guy Clark)

The Late Guy Clark was - and is - one of the great American treasures. If you don't think the greatest music comes from Texas, then you need to reconsider your position. There are so many great songs to pick from - but I pick this one because of Jerry Douglas' great dobro interlude. "Well, I wish I was in Austin, in the Chili Parlor Bar, drinking Mad Dog Margaritas. not caring where you are."

Angry All The Time (Bruce Robison)

Bruce Robison, the writer of this great song, once said, "There are two kinds of songs: sad songs and slightly faster sad songs." How true. (Of course, his greatest accomplishment was marrying the outstanding vocalist, Kelly Willis, who joins him in this performance.)

At Seventeen (Janis Ian)

This is the most bitter song I have ever heard. I dated a woman once - a professor - who shared a lot of the emotional baggage behind this song. When we parted, a lot of invective followed - you know, generational curses and that sort of thing. I don't think those of us on the other side of these relationships ever understand the depth of hurt that we witnessed - and I am not convinced we caused.