I have no idea how Bing Crosby felt about bebop. But given his roots, one can only assume he viewed the jazz style as noisy, foolish and faddish. A veteran of Paul Whiteman's band in the '20s and the sweet vocal romanticism of the '30s, Crosby preferred his jazz straightforward and laid back. Though he certainly became more jazz-minded by the '40s, his hip recordings during the decade were more likely a reflection of his ties to Decca and his exposure to the label's major jazz artists than specific personal choices.
One senses that Crosby was always a pop singer at heart and knew where his bread was buttered. You also sense that deep down he viewed jazz singing as necessary slumming. Smooth but edge-less, most of Crosby's recordings now sound hopelessly bland and dated. Creating large volumes of music that purposefully avoid making waves or taking risks will do that to your long-term legacy.
Throughout his career, Crosby was an eager novelty crooner, happily embracing all kinds of gimmicky songs bearing humorous twists and jokey lyrics—particularly if the material cast him as "jes folks." In some ways he had little choice, since there were only two types of songs then—straight renditions of American Songbook fare and cornball. He also knew that the more barbershop he seemed, the more likable he was and the more records he would sell. Which is certainly no crime. But to insist that his recordings are essential listening today would be stretching it in all honesty.
As far as I can tell, Crosby in the novelty category ventured into bop just once, recording Bebop Spoken Here twice in April 1949—once with with Patty Andrews and again with Peggy Lee. It's a goofy song but in both cases, Crosby doesn't seem to be in the spirit. And there's nothing like bebop to separate the at-ease from the uptight.
The Andrews' date occurred on April 14 for Decca with Victor Schoen and his Orchestra. The second was recorded during a live broadcast for Philco on April 27 with John Scott Trotter and his Orchestra. One assumes the latter was done on the radio in the wake of some moderate success for the first.
The initial version captures Andrews at her minxy best, scatting in cartoonish bop-ese. The second shows off Lee doing the same—but with a cooler and more sultry intonation. In both cases, Crosby executes smoothly but plays the surprised foil, as if embarrassed by the whole silly affair. It's impossible to know whether his superior and detached tone was scripted by cautious handlers or Crosby adapted that position himself to hedge any negative reaction from his core mainstream audience. To give Crosby the benefit of the doubt, one has to figure that Tony Bennett today would probably toss off a similar air if asked to rap a duet. Or maybe not.
Of course, the very fact that Bing Crosby was singing a bop novelty song in April '49 was a sure sign that the bop craze had crested. And in fact it had. Though bop would remain a staple of jazz for decades, new jazz styles were forming thanks to Miles Davis, Lennie Tristano, Lee Konitz, Gerry Mulligan and Clifford Brown. At least Crosby tried.