Bob Dylan began his career as a performing musician during a period when the vinyl LP was being adopted as a medium for creating an atmosphere and ambience. Frank Sinatra’s themed albums that evoked specific moods began appearing as 78 rpm disc collections from 1946.1 The more robust 12-inch, 33⅓ record was introduced by Columbia Records in June 1948, and allowed Sinatra to introduce albums on one long player (LP) with a series of acclaimed collections during the 1950s. Dylan has acknowledged Sinatra’s work throughout his career, even paying homage by performing “Restless Farewell” at the older performer’s 80th birthday celebrations in 1995, and releasing Shadows in the Night in 2015. The album featured renditions of songs popularized and defined by the interpretations of Sinatra and his imaginative arrangers and it was followed by Fallen Angels (2016) and Triplicate (2017) with further selections from the Great American Songbook (see Chapter 11).