It Never Entered My Mind
A & B
This is a song about a bewildered, self-inflicted loneliness. The protagonist reflects on the repeated warnings that never entered their mind. Now alone, they are forced to confront a diminished reality, getting by on their own.
The original setting of the song (1940) has the protagonist remembering her “darling dope” with fondness and longing. The word play keeps things from being too devastating. Benny Goodman’s version increases the tempo and punchiness, so the singer doesn’t sound beat up at all. “It never entered my mind” feels more like an assertion of toughness than an admission of personal fault.
Contrast that with Frank Sinatra’s first recording of the song. He takes the tempo very slow and gentle. He sings very close to the microphone, focusing on diction, tone, and melody. This is one of the most sad renditions. When he says “wish that you were there again,” you can feel the weight of that wish. The xylophone evokes the dancing starlight of the “wee small hours.” When he returned to the song a decade later for the album of that name, he sings it with more of the classic “Sinatrisms”. In my opinion, he sounds detached; he’s just singing a song.
The most famous interpreter is perhaps Miles Davis. He recorded it twice. On Workin’, his group
C
personal stories
D
expand on the subject or memory
E
free association