By Matt Caputo
By Devon Maloney
By Chris Chafin
By Village Voice
By Katie Moulton
By Hilary Hughes
By Gili Malinsky
By Bob Ruggiero
Mildred and Benny moved to Los Angeles, where they bought a house at 1307 Coronado, a few blocks off Sunset Boulevard. He was prospering with his bootlegging and she was earning a reputation singing sad songs in local dives. In 1925, she was working for tips at a speakeasy in the Hollywood Hills run by a friend, Jane Jones. The place was a converted private house set back from the road and surrounded by a fence. A lookout vetted customers and ushered them into a large crowded room with tables, a bar, and a small platform for the piano and singer. The regulars, many of them movie stars, could avail themselves of prostitutes as well as booze. When the spirit moved her, Jane Jones, a big woman with a brassy style (Crosby later featured her in his movie East Side of Heaven), would sing a song or two, but her customers preferred the cooing subtlety of Mildred, whose melodramatic warhorses, such as "Ships That Never Came In," generated a river of generous tips.
Mildred was working at Jane's when Al and Bing arrived, unannounced, on her doorstep, hoping she could help start them in show business. She took them in, encouraged them, advised them of auditions, played records she thought they ought to hear, and boarded them until they were on their feet, which did not take long. By then, she had become an obsessive cook, and Al was shocked to see how heavy she was. She instantly hit it off with Bing, who called her Millie. They both liked a good time and shared advanced and expansive tastes in music. Al found her "a little too barrelhouse for me," but to Bing she was "mucho mujer, a genuine artist, with a heart as big as the Yankee Stadium, and a gal who really loved to laugh it up." Within a year, Paul Whiteman hired the boys, who resolved someday to help her attain the break she deserved. Nearly three years later, they had their chance.
The Whiteman band returned to Los Angeles in 1929, to make King of Jazz, but everything went wrong, and after weeks of waiting for the studio to come up with a script, the frustrated bandleader prepared to pull out. Whiteman made it clear he was not hiring anyone, least of all another singer (he had turned down Hoagy Carmichael that week), but Bing and Al were certain that if they could just get him to hear Mildred he would fall under her spell. Millie had become friendly with several guys in the band that summer. She took them horseback riding, cooked up a storm, and served her home brew, which created a sensation, as good beer was hard to find. Bing and Al persuaded her to throw the band a farewell party. Whiteman, a prodigious beer drinker, happily accepted the invitation. As Bing recalled, "Paul didn't know it at the time, but he was a goner when he walked into the house."
Hoagy Carmichael, Roy Bargy, and Lennie Hayton took turns at her Steinway. Rinker described what happened next: "Bing turned to Mildred and said, 'Hey, Millie, why don't you sing a song?' No one had ever heard her sing, but they all joined in, 'Yeah, c'mon, Millie, let's have a song.' At first, Mildred acted reluctant, but I knew it wouldn't last long." She asked Al to accompany her on "(What Can I Say) After I Say I'm Sorry," and "she sang the hell out of the song." After a brief silence, everyone started to cheer, and Whiteman, who had been in the kitchen, asked who was singing. Bing barked, "That was Millie, Al's sister." Whiteman walked over, kissed her, and asked for an encore. "All her past experience singing in speakeasies and night spots came out as she sang. Her small, pure voice gave the songs feeling and meaning, and you knew you were hearing a singer who was very special," Al wrote. That night Paul hired her to sing "Moanin' Low" on his Old Gold radio show. Weeks later she was on a train to New York, a contract in her pursethe first "girl singer" to tour with an orchestra. A year later she was the highest-salaried performer on Whiteman's payroll.
She made her first record in 1929, with Eddie Lang, and became an instant favorite of the jazz elitethe one white woman (she preceded Lee Wiley and Connie Boswell by a couple of years) with an identifiable style who could hold her own in a field dominated by black singers. She had been one of the first to assimilate the styles of Bessie Smith (whose blues she sang in an audition for Hammond), Ethel Waters (whose lighter voice was closer to home), and Louis Armstrong (whose time and invention liberated everyone). She would emerge as a transitional figure between them and the band singers that followed, including Billie Holiday and Ella Fitzgerald, though Bailey had a style all her own. Her high, light voice inclined to a whirring in the top notes while packing plenty of power; her time and enunciation were exemplary. After a couple of years as a sidewoman, indulging in excessive vibrato, she rid herself of affect and ornamentation. She focused on the language of a song, the meaning, the special story it had to tell. She was funny, cool, smooth, and always in a groove.