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In 1939, Columbia Records refused to let Billie Holiday record the anti-lynching protest song "Strange Fruit". Milt Gabler invited her to record it for his small specialty label Commodore Records, and Columbia granted her a one-time exemption from her contract to do so, in which she recorded four songs (material for two 78rpm records). "Strange Fruit", backed with "Fine and Mellow", turned out to be the biggest selling record of her career. Although she continued to record for Columbia, in 1944, following the 1942–44 musicians' strike, Holiday permanently left Columbia for Commodore. Small labels like Commodore had been quicker to settle with the musician's union than large labels like Columbia, thus Holiday was able to return to recording quicker by switching to the smaller label. The Commodore tracks were more dominated by torch songs and dramatic ballads than her swing oriented Columbia material had been, although her later Columbia sides (e.g. "God Bless the Child") show she had already been evolving in this direction.
Later the same year, Holiday then followed Gabler to Decca Records, to record "Lover Man". Decca had allowed Gabler to keep his own label, while also being employed by them, so long as he directed all potential hits to Decca. Both Holiday and Gabler suspected "Lover Man" had the potential to be a hit, thus it became her first Decca single, and indeed another of her biggest hits. "Lover Man" was notable for featuring a string section, and all her Decca tracks typically featured string arrangements and even choral backing, rather than jazz combos. This was Holiday's choice, as strings were often used in the white pop records of the day, and when she recorded "Lover Man" she wanted the same sound offered to artists like Bing Crosby, and specifically her friend Frank Sinatra. During this same period, Holiday began performing in concert halls rather than nightclubs, and her live performances became more theatrical than jazz, with many of these dramatic songs becoming centrepieces of her set. Holiday continued to record for Decca throughout the 1940s, before again switching to Norman Granz's Clef label (later Verve) in the next decade.
The orchestras Holiday recorded with while at Commodore and Decca were variously led by Toots Camarata, Bob Haggart, Bill Stegmeyer, John Simmons, Buster Harding, Sy Oliver, and Gordon Jenkins.
"Big Stuff" was a Leonard Bernstein single, with Billie doing a new vocal to a song Bernstein had written as the prologue to his 1944 ballet Fancy Free . The b-side was another Bernstein song from the ballet, without Holiday: "Fancy Free (Galop Variation And Finale)" performed by the Ballet Theatre Orchestra Under Direction of Leonard Bernstein.
"You Can't Lose A Broken Heart" and "My Sweet Hunk O' Trash" were collaborations with Louis Armstrong.
"Guilty" was the only track not originally released as a 78rpm record, first appearing on the much later compilation LP The Blues Are Brewin' (Decca – DL 8701) in 1958. [4]
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