Hammond said the Wilson-Holiday records from 1935 to 1938 were a great asset to Brunswick. According to Hammond, Brunswick was broke and unable to record many jazz tunes. Wilson, Holiday, Young, and other musicians came into the studio without written arrangements, reducing the recording cost. Brunswick paid Holiday a flat fee rather than royalties, which saved the company money. "I Cried for You" sold 15,000 copies, which Hammond called "a giant hit for Brunswick.... Most records that made money sold around three to four thousand."
Another frequent accompanist was tenor saxophonist Lester Young, who had been a boarder at her mother's house in 1934 and with whom Holiday had a rapport. Young said, "I think you can hear that on some of the old records, you know. Some time I'd sit down and listen to 'em myself, and it sound like two of the same voices ... or the same mind, or something like that." Young nicknamed her "Lady Day", and she called him "Prez".