stylistic:style_transfer, linguistic:paraphrasing
1940–1947: Commercial success

Holiday's mother Sadie, nicknamed "The Duchess", opened a restaurant called Mom Holiday's. She used money from her daughter while playing dice with members of the Count Basie band, with whom she toured in the late 1930s. "It kept Mom busy and happy and stopped her from worrying and watching over me", Holiday said. Fagan began borrowing large amounts from Holiday to support the restaurant. Holiday obliged but soon fell on hard times herself. "I needed some money one night and I knew Mom was sure to have some", she said. "So I walked in the restaurant like a stockholder and asked. Mom turned me down flat. She wouldn't give me a cent." The two argued, and Holiday shouted angrily, "God bless the child that's got his own", and stormed out. With Arthur Herzog, Jr., a pianist, she wrote a song based on the lyric, " God Bless the Child ", and added music. "God Bless the Child" became Holiday's most popular and most covered record. It reached number 25 on the charts in 1941 and was third in Billboard ' s songs of the year, selling over a million records. In 1976, the song was added to the Grammy Hall of Fame. Herzog claimed Holiday contributed only a few lines to the lyrics. He said she came up with the line "God bless the child" from a dinner conversation the two had had.

On June 12, 1942, in Los Angeles, Holiday recorded " Trav'lin Light " with Paul Whiteman for a new label, Capitol Records. Because she was under contract to Columbia, she used the pseudonym "Lady Day". The song reached number 23 on the pop charts and number one on the R&B charts, then called the Harlem Hit Parade. On October 11, 1943, Life magazine wrote, "She has the most distinctive style of any popular vocalist, is imitated by other vocalists."

Milt Gabler, in addition to owning Commodore Records, became an A&R man for Decca Records. He signed Holiday to Decca on August 7, 1944, when she was 29. Her first Decca recording was " Lover Man " (number 16 Pop, number 5 R&B), one of her biggest hits. The success and distribution of the song made Holiday a staple in the pop community, leading to solo concerts, rare for jazz singers in the late 1940s. Gabler said, "I made Billie a real pop singer. That was right in her. Billie loved those songs." Jimmy Davis and Roger "Ram" Ramirez, the song's writers, had tried to interest Holiday in the song. In 1943, a flamboyant male torch singer, Willie Dukes, began singing "Lover Man" on 52nd Street. Because of his success, Holiday added it to her shows. The record's flip side was " No More ", one of her favorites. Holiday asked Gabler for strings on the recording. Such arrangements were associated with Frank Sinatra and Ella Fitzgerald. "I went on my knees to him", Holiday said. "I didn't want to do it with the ordinary six pieces. I begged Milt and told him I had to have strings behind me." On October 4, 1944, Holiday entered the studio to record "Lover Man", saw the string ensemble and walked out. The musical director, Toots Camarata, said Holiday was overwhelmed with joy. She may also have wanted strings to avoid comparisons between her commercially successful early work with Teddy Wilson and everything produced afterwards. Her 1930s recordings with Wilson used a small jazz combo; recordings for Decca often involved strings. A month later, in November, Holiday returned to Decca to record " That Ole Devil Called Love ", "Big Stuff", and " Don't Explain ". She wrote "Don't Explain" after she caught her husband, Jimmy Monroe, with lipstick on his collar.

Holiday did not make any more records until August 1945, when she recorded "Don't Explain" for a second time, changing the lyrics "I know you raise Cain" to "Just say you'll remain" and changing "You mixed with some dame" to "What is there to gain?" Other songs recorded were "Big Stuff", " What Is This Thing Called Love? ", and "You Better Go Now". Ella Fitzgerald named "You Better Go Now" her favorite recording of Holiday's. "Big Stuff" and "Don't Explain" were recorded again but with additional strings and a viola. In 1946, Holiday recorded " Good Morning Heartache ". Although the song failed to chart, she sang it in live performances; three live recordings are known.

In September 1946, Holiday began her only major film, New Orleans, in which she starred opposite Louis Armstrong and Woody Herman. Plagued by racism and McCarthyism, producer Jules Levey and script writer Herbert Biberman were pressed to lessen Holiday's and Armstrong's roles to avoid the impression that black people created jazz. The attempts failed because in 1947 Biberman was listed as one of the Hollywood Ten and sent to jail. Several scenes were deleted from the film. "They had taken miles of footage of music and scenes", Holiday said, but "none of it was left in the picture. And very damn little of me. I know I wore a white dress for a number I did... and that was cut out of the picture." She recorded "The Blues Are Brewin'" for the film's soundtrack. Other songs included in the movie are " Do You Know What It Means to Miss New Orleans? " and "Farewell to Storyville". Holiday's drug addictions were a problem on the set. She earned more than one thousand dollars per week from club ventures but spent most of it on heroin. Her lover, Joe Guy, traveled to Hollywood while Holiday was filming and supplied her with drugs. Guy was banned from the set when he was found there by Holiday's manager, Joe Glaser.

By the late 1940s, Holiday had begun recording a number of slow, sentimental ballads. Metronome expressed its concerns in 1946 about "Good Morning Heartache", saying, "there's a danger that Billie's present formula will wear thin, but up to now it's wearing well." The New York Herald Tribune reported of a concert in 1946 that her performance had little variation in melody and no change in tempo.