The German-born model and singer Nico is certainly of a time. Her voice hearkens to an era when music was simply different—and candidly, not so overproduced. She is part Bob Dylan and part Lou Reed.

Chicago singer-songwriter Chris Connelly regularly releases an album of new material on his November birthday. For his latest record, Eulogy to Christa: A Tribute to the Music and Mystique of Nico, he ...