This series is a documentary-style road trip and cultural primer with Michael Feinstein as the leader of an expedition through the history of American popular song. Viewers follow him both on stage and backstage, hear personal stories about the songwriters and entertainers he has known over a 30-year career, travel to flea markets, dig through dusty storage units, and swap treasures with fellow collectors. Rare archival audio and film footage combine to reveal the social and historical forces behind the music that helped shape the style, attitude, and self-image of America for more than a century. Filled with generous portions of live performance, this series offers both an intimate portrait of a unique entertainer, and a history of 20th century pop culture.