Ask anyone to name the greatest entertainer of the 20th century and responses will likely range from Sinatra and Garland to Elvis and Aretha. Chances are Bing Crosby will rarely, if ever, be mentioned. At his height, Crosby was untouchable, the world’s first multimedia superstar; but after his death in 1977, age 74, his star faded quickly. Fortunately, back in 2001, esteemed jazz and film writer Gary Giddins set out to fully chronicle his tremendous heft, publishing A Pocketful of Dreams, spanning Crosby’s first 36 years, from his early days in Spokane to his rise to the top of the Hollywood heap.
Expectation was that Giddins would shape a companion volume covering the rest of Crosby’s life. Instead, part two of what will ultimately stand as the definitive Crosby analysis and appreciation covers just seven years. As Giddins so superbly demonstrates, more than any other period, the stretch from the early- to mid-1940s was not only Crosby’s most influential but also served to shape a canonized public persona that lasted his lifetime.