Long John Blues by Dinah Washington (1949)

The narrator of Long John Blues has a toothache, goes to see a dentist named Long John, and reports that he is extremely good at his job. He fills her "cavity". He has a "drill". He tells her to open wide and she does. It was a top-three rhythm and blues hit in 1949, and a reminder that the golden age of the double entendre was not the sixties or the seventies but the years immediately after the war, when records like this sold in enormous numbers to an audience that understood every word and booked a check-up.

Washington's delivery is the whole thing. She sings it as a woman describing an appointment, with total composure, and the composure is the joke: the more matter-of-fact she is about the dentist's technique, the funnier it gets. The band swings hard behind her and the saxophone takes a solo that is, in context, fairly rude, and possibly a second opinion.

Its afterlife is an introduction. Most people know her for What a Diff'rence a Day Makes and have never been told about Long John; this is where they get told. With the trombone record five years later it makes the case that Dinah Washington was the most sophisticated dirty-song singer of her era, and the only woman on this list with two entries, both involving tools.