The author of a recent exhaustive biography of Bing Crosby, Gary Giddins, laments that Crosby's imprint has badly faded in recent years. As one participant in a 2002 Crosby conference at Hofstra University in Hempstead, New York, commented: “The image of Frank Sinatra is that of a stylish man standing in the spotlight, in front of a microphone, but the image of Bing Crosby is a grandfatherly man wearing a floppy hat with a golf club on his shoulder.” With the observation that, among other astonishing achievements, Crosby recorded more than four hundred hit songs over a period of thirty years, Giddins asks: “Could a man who spoke so deeply to so many for so long have nothing to say to us now?” Crosby's true standing as an innovative artist, “the epitome of cool,” has been diminished, in Giddins’ view:

But while Giddins is right that Crosby's star has unquestionably dimmed, the preceding comment also points to the seeds of influence that Der Bingle indeed planted with baby-boomers. Crosby's influence on his grandchildren's generation— the rock ‘n’ roll generation—can be seen in a 1993 documentary hosted by comedian Dennis Miller, “Bing! His Legendary Years, 1931–1957,” in which Miller, the “ranting” star of “Saturday Night Live,” HBO specials, and “Monday Night Football,” proclaims his admiration for Crosby. “Nowadays, people may notuse the words ‘Bing Crosby’ and ‘hip’ in the same sentence, but the fact is, I think he embodied the word,” Miller said. Miller described his mother dragging him out of a movie theater after watching one of the Bing Crosby-Bob Hope “Road” movies over and over.