Frank: The Voice by James Kaplan

DiMaggio swinging a bat, Sinatra made it
look
easy.
    A quarter century later, Simon wrote in
Billboard
what he really thought of Sinatra that night: “He sounded somewhat like a shy boy out on his first date—gentle, tender but frightfully unsure of himself.” Be that as it may, when the Music Makers hit the Panther Room of the Hotel Sherman in Chicago a couple of weeks after the Roseland gig, Betty Grable, whose star was rising in Hollywood (and who would in a few years replace Louise Tobin as Mrs. Harry James), dragooned a young reporter named James Bacon into going to hear Sinatra. Bacon had never heard of the guy. “I’ll never forget,” he recalled years later. “The minute Sinatra started singing, every girl left her partner on the dance floor and crowded around the microphone on the bandstand. He was so skinny, the microphone almost obscured him.”
    Afterward, Bacon congratulated Harry James on his new boy singer. “Not so loud,” James replied. “The kid’s name is Sinatra. He considers himself the greatest vocalist in the business. Get that! No one ever heard of him. He’s never had a hit record. He looks like a wet rag. But he says he is the greatest. If he hears you compliment him, he’ll demand a raise tonight.”
    Frank Sinatra was anything but unsure of himself. Along with his abilities, the other thing he was certain of was precisely how the girls liked him to sound. The boys didn’t always agree. During the Chicagostand, a
Billboard
reviewer wrote that Sinatra sang “the torchy ballads in a pleasing way in good voice,” but then went on: “He touches the songs with a little too much pash, which is not all convincing.”
    Or maybe all that pash was simply unsettling because it was so new. Among the smooth-as-silk baritones of the day, led by Crosby, Sinatra was an anomaly, a hot artist rather than a cool one, a harbinger of his own singular future.

    Harry James, too, was a hot artist: a hepcat, a weed-puffing wild man. He was also a strangely self-defeating character—alcoholic, remote, and persistently broke. That summer, he lost everything he had in a settlement over an auto accident. (Connie Haines, whose salary he could no longer afford, had to leave.) And in a country crowded with big-band talent—Tommy Dorsey, Benny Goodman, Charlie Barnet, Count Basie, Jimmy Dorsey, Duke Ellington, Bob Crosby, Jimmie Lunceford, Glenn Miller, and Artie Shaw were all crisscrossing the land with their outfits in the swinging late 1930s—James was having a hard time making a go of it. Some nights, as the Music Makers worked their way westward, the band only pulled down $350—and that had to pay seventeen band members and a bus driver, not to mention defray food, gas, and accommodations. There were times the outfit seemed snakebit. Other bands had hit records; Harry James couldn’t catch a break. Meanwhile, a music-business brouhaha—the three-way royalty beef between ASCAP, the American Federation of Musicians, and the radio stations, a dispute that led ASCAP to ban radio performances of all the songs it licensed—didn’t help.
    Frank Sinatra, who would record over thirteen hundred songs in his career, cut just ten sides in his six months with the Harry James band. The first time he went into the Brunswick studios at 550 Fifth Avenue—the date was July 13, 1939—was only the second time he had ever set foot in a recording studio. In all, Sinatra and James recorded three times in New York that summer (subsequent sessions would takeplace in Chicago in October and Los Angeles in November), on each occasion laying down two sides of a 78-rpm platter. The third session took place on Thursday, August 31, the day before the Nazis stormed through Poland—cool and cloudy in Manhattan; double-decker buses cruising up Fifth Avenue; big fans whirring in the studio. That day the Music Makers recorded one take of a soupy, utterly forgettable Frank Loesser ballad called “Here Comes the Night” (“Here comes