[3] The family moved again, this time to Oklahoma City, where Sherman was again drawn into the bootlegging business by another of his older brothers.

When his brother ran out on his Detroit mob partners, he left for New York, with Sherman joining him within a short time.

[4] He promoted the club by selecting prominent debutantes to frequent parties there and bring in society cliental.

In 1941, he dubbed Betty Cordon, a debutante from North Carolina, as New York's "Number One Glamour Girl"[5] One of Billingsley's mistresses in the late 1930s was actress Ethel Merman.

Billingsley married Hazel Donnelly (1902–1991) on August 25, 1924, and they had three daughters, Jacqueline (Rorke, 1926–1998), Barbara (Mohler, ~1936–2010), and Shermane (1944–2023).