In this article, the author describes his use of an old obsolete and quaintly archaic form of entertainment in order to create a more lively academic discussion. He introduced the songs of Scottish folk/pop singer, Al Stewart, as an effective teaching tool in his class. Students listened to several Al Stewart songs: (1) "A League of Notions"--a wary and sardonic account of the mess European leaders made of their own continent after the Great War; (2) "Lindy Comes to Town"--a glance at the sanguine and booming America of 1927 framed by Charles Lindbergh's solo flight to Paris; (3) "Trains," a long narrative that documents the history of rail travel, but also serves as a grim reminder of the Holocaust; and (4) "Post World War Two Blues," a song that documents the attitudes that developed after that war. The author notes that, although the class treated Stewart's music no differently than they had treated Hawthorne's novels, Dickenson's poetry, or Willa Cather's short stories, he had always appreciated how seamlessly Stewart's work fit into academic discussions.