I'm a Fool to Want You 1958 Billie Holiday

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Frank Sinatra first recorded the song with the Ray Charles Singers, in an arrangement by Axel Stordahl in New York 1951. It is commonly thought by many listeners that Sinatra was navigating his stormy marriage to Ava Gardner at the time, but Sinatra and Gardner didn't marry until November 7, 1951, nearly 8 months after the song was recorded. It is more likely that he was melancholy about his wife Nancy's refusal to grant him a divorce so he could marry Gardner and his guilt for the impact his very public affair with Gardner was having on his family, especially his three children. To complicate matters, his career was in a freefall and he and Nancy were both Catholics and the Church forbade divorce. His emotional rendering of the song is haunting and it instantly became one of the classic "saloon songs"
It would not have escaped Sinatra that his unbridled and uncontrollable passion for Gardner and the consequential collateral damage it caused his family, reputation, and career made him a fool, not only in his own eyes, but to the world. So, he felt the song was perfect for his current situation and, for him personally, somewhat cathartic. As Gay Talese wrote in his 1966 article for Esquire, "Frank Sinatra Has a Cold," "A friend who was in the studio when Sinatra recorded it recalled: 'Frank was really worked up that night. He did the song in one take, then turned around and walked out of the studio and that was that ... "Writer Mark Steyn quotes longtime Sinatra arranger Nelson Riddle as saying, "It was Ava who taught him how to sing a torch song. That's how he learned. She was the greatest love of his life and he lost her."
The song has become a pop and jazz standard that has been recorded by more than 100 other performers, including Mitski, Billie Holiday, and Bob Dylan.