Iris Dement's charming 1992 debut, Infamous Angel, came across as a family scrapbook filled with rustic reminders of front-porch romances and back-yard daydreams, a twangy celebration of country-music tradition and small-town life from a sweet-voiced optimist who looks at the Mason jar and always says it's half full.

But her new album, My Life, is more like a diary, a bittersweet collection of...