Eleanora "Billie Holiday" Fagan (1915) was just about the opposite from Ella Fitzgerald. Her singing was all about class (her range was just a little over one octave) and emotion (the sound of pain, of both ancestral and personal pain), not power or virtuosity. She had a fondness for disturbing material, and none of her classics was joyful: Abe Lyman's I Cried For You (june 1936), Abel Meeropol's Strange Fruit (april 1939), a protest song about a lynching, her own Fine and Mellow (april 1939), Arthur Herzog's God Bless the Child (may 1941), about the "Great Migration", Johnny Green's I Cover The Waterfront (august 1941), Rezso Seress' Gloomy Sunday (august 1941), about suicide, Roger "Ram" Ramirez's Lover Man (april 1944). Instead of simply delivering lines, Holiday would make each note sigh, bleed and cry. They proved her the closest thing to a French chansonnier that American jazz ever had.
The backing was not orchestral but rarified, mostly by small combos led by Benny Goodman's pianist Teddy Wilson. She recorded with Lester Young a few numbers in a sophisticated chamber-jazz style: George Gershwin's The Man I Love (december 1939) and Seymour Simons' All of Me (march 1941).
For her excesses of drugs and alcohol, she was banned from night-clubs and arrested repeatedly. She died poor at 44 in 1959.