Between 1936 and 1967, the Negro Motorist Green Book was essential for the survival of thousands of Black Americans in an era of segregation cemented into the American legal system through Jim Crow laws, sundown towns where Black Americans were under threat of violence by white supremacists after sunset, and a sharp increase in lynchings and other forms of hate crimes. For the last year we’ve been working with Candacy Taylor, one of our African American Cultural Heritage Fund fellows, to further explore sites that were included in the Green Book. The 101 Ranch was featured in the Green Book in 1938.

At a time when women couldn’t get credit from a bank or even have their own bank account, Black women found a measure of success and independence by listing their businesses in the Green Book. Nearly 900 hair salons and beauty colleges, more than 1,400 tourist homes (similar to Airbnbs), and dozens of nightclubs were run by women. One of the most outrageous female-run nightclubs I discovered in the Green Book was a sex club in Harlem called the 101 Ranch.

The 101 Ranch, also known as the Daisy Chain, was one of the most popular nightclubs in the 1930s in Harlem. It was run by an international singer and chorus dancer named Hazel Valentine. She was known as “the Red Vampire” and performed throughout the United States and in Europe. Valentine danced in Josephine Baker’s show in Paris, "La Revue Nègre," in 1925 and at “Tan Town Topics” in 1926 at Harlem’s Lafayette Theater (another Green Book site).

While Leroy McDonald and Walter Clark ran the club, it was Valentine who made it one of the most notorious in Harlem history after she featured entertainers who celebrated sexual freedom. Housed in a large railroad flat with a long hall with rooms off to the side, the 101 broke all the rules; it was a place where customers—both Black and white—knew they could explore their fantasies and fetishes.

In addition to a sex club, the 101 Ranch was also a gay cabaret featuring a chorus line of entertainers and drag queens. Sepia Gloria Swanson was a celebrated figure in the Harlem drag scene and lived her life in sequins and feather boas while dancing to “Squeeze Me,” her signature song by Fats Waller. Another memorable drag queen at the 101 was Clarenz, a six-foot-tall svelte female impersonator and acrobat.

Despite its infamy, the 101 Ranch was widely popular among the celebrities. Billie Holiday was a regular, and in 1937 Count Basie wrote “Swinging at the Daisy Chain” to commemorate the club. Fats Waller also wrote a song about it, called “Valentine Stomp” after Hazel. He loved the place so much he even helped pay the rent when money wasn’t flowing as freely as the liquor.