Bada Bing!

Bing Crosby--a hipster? Sure, he may have cut more No. 1 singles than the Beatles, but was the smoothly affable elder statesman of Eisenhower-era middle-brow pop ever really...cool? You bet. In Bing Crosby: A Pocketful of Dreams--The Early Years, 1903-1940 (Little, Brown; 728 pages; $30), critic Gary Giddins takes a fresh and compelling look at the forgotten first half of Crosby's long career, turning the clock back to the Roaring Twenties to show how Crosby started out as a hard-drinking, hard-swinging jazzman whose nonchalant way with a song was universally regarded, even in Harlem, as the height of hipness.

The young Crosby, Giddins argues convincingly, was a major musical innovator who all but single-handedly created the modern manner of microphone-assisted singing that dominates pop to this day. He roomed with Bix Beiderbecke, recorded St. Louis Blues with Duke Ellington and formed a mutual-admiration society with Louis Armstrong (Louis taught Bing how to scat; Bing taught Louis how to croon).

By 1940, Crosby had reinvented himself as an easy-to-take movie star, turning his back on hot jazz in order to serve up "musical comfort food" for the masses. But the cutting-edge Crosby of A Pocketful of Dreams remains undiminished by the bass-baritone blandness of his postwar incarnation as the Ghost of Christmas Specials Past. By concentrating on Bing Crosby the jazz master, Gary Giddins does him justice at last.