Bing Crosby was, without a doubt, the most popular and influential multi-media star of the first half of the twentieth century. His remarkable appeal, which continues to this day, was in his seemingly effortless ability to pull an audience in to his intimate, laid-back voice and innate charm. For over three decades, through radio, film, television, and records he reigned supreme. A brilliant entrepreneur, Crosby played an important role in the development of the postwar recording industry. As one of Hollywood's most popular actors, he won the Oscar for 1944's Going My Way and starred in the iconic "Road" films with Bob Hope. Crosby recorded nearly 400 hit singles, an achievement no one-not Sinatra, Elvis or the Beatles-has come close to matching. Thirty-seven years after his death, he remains the most recorded performer in history. Narrated by Stanley Tucci and directed by Emmy-winner Robert Trachtenberg (American Masters-Mel Brooks: Make a Noise), this film explores the life and legend of this iconic performer, revealing a personality far more complex than the image the public had only thought they'd known.