Bing Crosby might seem an unlikely subject for Gary Giddins, best known as jazz columnist for the Village Voice and author of the 1998 National Book Critics Circle Award winner Visions of Jazz. Yet Giddins found the subject so absorbing that Bing Crosby: A Pocketful of Dreams (Little, Brown) closes in 1940, the year the already popular singer and radio personality became a mega-movie star with the release of Road to Singapore. There was just too much interesting material to cram into a single volume, says Giddins, though he admits he was initially skeptical when Paul Bresnick, who had edited his previous biography of Louis Armstrong, suggested he might want to write at length about Der Bingle.

"I had always loved Crosby's early records.In fact, there's a chapter about him in my very first book, Riding on a Blue Note," recalls the writer, seated in the book- and CD-crammed office of his Greenwich Village apartment. "But I didn't take the later music seriously, and I didn't know the movies. When I looked into it, I was shocked to discover that no one had ever written about him seriously. There had only been fan books and a hatchet job.

"Two things began to interest me about him as a subject for a book," says Giddins. "First of all, I could use Crosby to trace the whole development of American popular culture, something I had always wanted to do. Just by telling his story, I can show how records, radio and movies developed. I can talk about the conversion from acoustic to electric recordings, which changed the way we hear music and was conducive to recording baritones like Crosby. I can talk about the development of radio and the condenser microphone. [Crosby's fabled skill with the mike fostered a more intimate singing style.] I can talk about the change from silent to sound movies, Crosby being one of the first major stars of talking pictures. He was at the center of so many different aspects of the cultural life of that period."

Ironically, Giddins's second reason for thinking a Crosby biography might be interesting proved to be based on misinformation. "I believed the hatchet job," he says, referring to Donald Shepherd and Robert F. Slatzer's controversial 1981 book, Bing Crosby: The Hollow Man. "I assumed that he was an SOB in private life, and this fascinated me: how d s someone who's cold, remote and disagreeable in private create the public illusion that he's the soul of warmth? I thought that was a valid subject. I find so many show business biographies distasteful because they feel like they were written by a puritan tribunal: they take people to task for being philanderers or whatever, and this interferes with the way they see the work. I wanted to connect the two." With this in mind, Giddins wrote a proposal, and his agent, Georges Borchardt, got "a pretty good advance" from Morrow, where Bresnick was an editor. But when he began conducting interviews for the book, Giddins remembers ruefully, "Everybody I talked to said they loved him! It turned out that nothing in The Hollow Man stands up. Their primary source, Al Rinker [Crosby's piano-playing partner in vaudeville and for many years after], was so offended by the book that he wrote a private journal to correct it." Rinker's daughter gave Giddins a copy of the journal, one of the many invaluable primary sources that turned up in those serendipitous, unexpected ways every nonfiction writer cherishes. Crosby's nephew casually handed over a decade's worth of correspondence and legal papers that clarified the singer's fraught business relations with his brothers. A massive cache of letters discarded by Crosby's first wife, Dixie, not only provided a detailed picture of his finances but also gave a much more favorable impression of his behavior toward her as their marriage foundered. Giddins first heard about those letters when they were owned by a collector who declared he would burn them before he'd let Giddins see them. A Pocketful of Dreams was in page proofs when Giddins learned that the collector had given them to the editor of a Crosby fanzine with whom he had a cordial relationship. An impassioned phone call and "the most diplomatic letter I've ever written" persuaded the fanzine editor to send them along.

"I find so many show business biographies distasteful because they feel like they were written by a puritan tribunal."

"It was one of those miracles that makes you really believe there is a Being looking out specifically for you--and this is a major concession for an atheist," jokes Giddins. The letters will be a major source for volume two, but a couple were relevant to the final pages of volume one. Little, Brown delayed printing so that Giddins could rewrite; the new passages were completed so close to publication they aren't even in the advance galleys.

The saga of how a one-volume Bing Crosby biography contracted by Morrow turned into two volumes for Little, Brown is long and stormy, involving several changes of management and one of corporate ownership. Giddins likes a good publishing horror story as well as the next battle-scarred book author (he's published seven books with four companies), and his account contains the usual complaints about unreasonable deadlines and unsympathetic executives--but never about Bresnick, whose "hands were tied." He's grateful to Borchardt for keeping him on a (relatively) even keel throughout, and to Little, Brown publisher Sarah Crichton for picking up the biography and serving as its editor.

The one good result of all this aggravation was Visions of Jazz, originally slated to be Giddins's fourth collection of essays with Oxford University Press. During his wrangling with Morrow, at a point when "I couldn't work on Crosby while I felt nobody gave a damn," the author turned to the Oxford project and discovered he no longer wanted to simply rework previously published articles. "I called up Sheldon Meyer, who had edited the previous collections, and said, 'I just don't have the heart for this. These pieces don't mean anything to me anymore. I want to do a real book.' " Giddins proposed chronicling the 100-year history of jazz through portraits of individual musicians, thematically organized to trace the art form's evolution from "a new music" to "a mainstream music" to "an alternative music" and beyond. Meyer, a jazz buff responsible for Oxford's distinguished publishing in the field, liked the idea, and the result justified his faith. Visions of Jazz vividly displays Giddins's ability to appreciate individual artists' contributions and connect them to a larger story in elegant, enthusiastic prose.

"When you read most jazz histories, you would think jazz existed in some vacuum," the author says. "Popular music, even a world war, they never intrude. It's very evident to me that jazz always reflects the period: the big bands must be during the depression, the avant-garde must be during the '60s. They reflect what's going on in the world; you have to keep bringing that in. Jazz has always bounced off popular culture, from the time Louis Armstrong sang 'Body and Soul' to avant-garde guys playing James Brown riffs."

In taking this broad-ranging, populist approach, Giddins was influenced by the literary critics he admired as a teenager: "Edmund Wilson, Max Beerbohm--Dwight Macdonald was the guy who made me become a writer in the first place. I liked things like his essay on the political meaning of Ben-Hur. It was funny and interesting, and it was the way I understood life and what writing ought to be."

Growing up on Long Island, he was a bookish kid immersed in classic American literature from Hawthorne to Hemingway, Fitzgerald and Faulkner. "Then I started going down the list of National Book Award winners: Bellow, Roth, Ellison, Malamud, Walker Percy. I wanted to be a novelist, because that was what literary people do."

Jazz entered his life like a thunderbolt in 1963, when 15-year-old Gary was on vacation in New Orleans. "Here's a good example of the sociological/historical connection," he says. "The bus pulls up in front of our hotel, I look out the window and see three doors: Men, Women, and Colored Men--Colored Women must have been around the corner. I was brought up in a liberal household where racism was considered the ultimate human sin, and this just gave me the feeling, you're not in Kansas anymore. Then Sunday afternoon, we go to hear jazz at the Royal Orleans Hotel, strictly because that's what tourists do. I walk into this room, and there are black and white people smoking and holding cocktail glasses and talking together. I'd never seen that, even in New York. I thought, 'Wow! This jazz world is really something.' The music was exhilarating, but the whole experience was amazing."

Back in New York, he went out and bought "the album that changed my life": a Columbia recording of Louis Armstrong playing with Earl Hines. "I had grown up with classical music, and I thought the absolute summit of Western civilization was the B-minor Mass. The tracks on this record--'Basin Street Blues,' 'Tight Like That,' 'Muggles'--were the first music that ever moved me emotionally that way, just made the hairs on my neck stand up. From that point on, I was lost. I still thought I was going to be a novelist, but I was completely obsessed with jazz."

At Grinnell College in Iowa, Giddins infuriated rock-oriented students by spending the entire concert budget on jazz acts: "When I brought Cecil Taylor [described in Visions of Jazz as "the eternal outer curve of the avant-garde"], there was actually an impeachment trial in the student congress; I barely squeaked out a vote of confidence." He majored in English, still intending to write fiction until his favorite teacher bluntly told him a short story he'd written was "just terrible." Happily for Giddins's self-esteem, the professor went on to say that he had "an obvious gift for criticism" and should pursue that. "I walked out of there on air," he recalls. "I didn't care that he hated the story. It was the first vote of confidence I'd ever gotten as a writer."

After graduation, Giddins tried to sell jazz reviews to the new rock magazines and got "really nasty rejection letters, not just saying no, but sounding like I was some sort of apostate." It wasn't easy being a jazz fan at the height of rock's hegemony in pop music. Giddins had just started his column at the Voice (named "Weather Bird" in honor of a track on that life-changing Armstrong/Hines album) in 1973 when Robert Christgau became the new music editor. "All I knew about Christgau was that he was a rock critic who had written a piece in Esquire about how much he hated Miles Davis!" Fortunately, Christgau liked Giddins's work, and the two "hit it off right away. Bob is the best line editor I've ever had, and I've worked with some great ones, including Sarah Crichton. But Bob is extraordinary: he's generous, he's scrupulous, and I have learned so much about writing from him."

In Riding on a Blue Note (1981), the first of his three collections published by Oxford, Giddins took some of his longer pieces from the Voice, rewrote and reorganized them to create a unified exploration of the links between jazz and pop. Rhythm-a-ning (1985), "a canvas of where jazz was in the '80s," is the closest to a straight anthology, and Faces in the Crowd (1992) is the author's personal favorite. "Sheldon Meyer suggested doing a reader, which would include my film and literary criticism, and it was a big failure: jazz people didn't think it had enough jazz to warrant their interest, and I didn't have a reputation as a book or movie reviewer, so none of them covered it. But it was written when my wife [Deborah Halper] was pregnant and our daughter [Lea] was born, up until the time she was about two. I was very, very unreasonably happy during that period, and when I look at the book I see that happiness on every page."

Giddins is proud of Celebrating Bird (Beech Tree, 1986), the first substantive portrait of Charlie Parker, and of Satchmo (Dolphin, 1988), a revisionist argument that Louis Armstrong's later music was as important as his revolutionary work in the 1920s, but he considers them "extended essays" rather than full biographies. He believes he worked at a new level of ambition in Visions of Jazz and Bing Crosby, which he sees as companion volumes wrapping up longtime preoccupations. "If anyone wants to know what I know or think about jazz after 35 years of listening to the music, Visions of Jazz is where they would find it." Volume two of Bing Crosby, he adds, will carry his case study of the entertainment industry into the age of television. "In 1946, Crosby singlehandedly changed radio from a live medium to a prerecorded medium. This has been forgotten, because a year later television arrived and radio seemed irrelevant, but television followed the same arc, from a live medium to prerecorded broadcast on videotape. It's a great story."

He's not really sure what comes after that story. "I'm about to take my first vacation in nine years, then there's the book tour, then it's back to volume two that will be my jail for a while."

Smith, a frequent contributor to PW, is the author of Real Life Drama (Knopf).