Discs one through six, and disc seven tracks one through fourteen present the master takes in chronological recorded order. The remainder of disc seven, and discs eight through ten, present the alternate takes and other items, also in chronological recorded order. The other items consist of eight tracks not part of the general body of Wilson/Holiday recordings from 1935 to 1941. The first, track 15 of disc seven "Saddest Tale" with the Duke Ellington Orchestra, was taken from the soundtrack to the movie short Symphony in Black by Paramount Pictures in 1935. Disc eight, tracks three through five, contain airchecks with the Count Basie Orchestra from 1937, the only documentation of Holiday's year-long tenure as Basie's band singer. Disc nine, tracks seven and eight, feature recordings broadcast on the Camel Caravan radio variety program of January 17, 1939; with backing by the Benny Goodman Orchestra, Billie sings alongside Johnny Mercer, Martha Tilton, and Leo Watson on the second song, Mercer's "Jeepers Creepers".
The final two tracks of the set, numbers 22 and 23 of disc ten, are from the Esquire Award Winners Concert at the Metropolitan Opera, broadcast and recorded on V-Discs for distribution to servicemen fighting overseas during World War II. Holiday had won top female jazz vocalist for 1943, and became the first African-American woman to sing at the Met. "Do Nothing 'Til You Hear From Me" and "Billie's Blues," under a different title, are performed accompanied by other Esquire poll winners, Roy Eldridge, Barney Bigard, Art Tatum, Al Casey, Oscar Pettiford, and Sidney Catlett. This recording took place more than two years after the final studio session in 1941, and during the Petrillo recording ban; the AFM waived the strike terms for the recording of V-discs.