I have to admit that I was hesitant to make Rickie Lee Jones’ Pirates the subject of this week’s Cratedigger. The weather has been gloomy here in New Jersey all week, the Yankees dropped the first game of the World Series to Philadelphia, and my finances are in the sewer. Since Pirates is perhaps the most heartbreaking album I’ve ever encountered, I was afraid listening to it again would throw me into an even deeper funk. Despite the sorrow, when pressed, I will tell you that Pirates is one of the best albums ever made, and it is easily ensconced in my personal Top Five, where it has resided since its release in July, 1981.

Rickie Lee Jones burst on the scene with her eponymous debut, and it’s massive hit single, “Chuck E.’s In Love,” in 1979. She was part of a bohemian L.A. crowd that included the aforementioned Chuck E. Weiss and singer/songwriter Tom Waits, with whom Jones was in a relationship. The songs on her second album, Pirates, are largely a wistful reflection on her time with Waits, following their breakup. “We Belong Together,” “A Lucky Guy,” and the title track all refer to her relationship with him, and “Living It Up” and “Traces of the Western Slopes” (written with new boyfriend Sal Bernardi) are peopled with characters from the bohemian milieu that they moved in. The most devastating heartbreak of all, however, comes in the song “Skeletons,” based on the true story of a young man who was killed by the Los Angeles police in a case of mistaken identity as he was driving his wife to the hospital to give birth. (more…)