The Drag Queen or Ladies and Gentlemen paintings were the idea of a protegé of the art dealer Iolas named Anselmino. He had previously commissioned Andy to do an edition of one hundred prints of Warhol's Man Ray portrait. When Andy went to Turin to sign the prints, he said that he wanted to commission a larger edition of prints, and maybe paintings as well. He first suggested that Andy do a series of drag queens, suggesting portraits of Candy Darling, Jackie Curtis and Holly Woodlawn. Andy told him that Candy was dead and that dealing with Jackie and Holly would drive him crazy. He asked Anselmino to come up with another idea.
Later, at dinner, Anselmino suggested doing a series of "funny-looking" transvestites - ones with beards who were obviously men trying to pass as women. Andy suggested putting a wig on Bob Colacello who was at dinner with them.
Bob did pose in a wig for Andy but it was unusable. Most of the models were found (at Andy's suggestion) at The Gilded Grape - "a bizarre little bar on Eighth Avenue and West 45th Street, frequented by black and Hispanic transvestites (average height: six feet two) and white truck-driver types (average weight: 275 pounds)". (BC222)
"We would ask them to pose for 'a friend' for $50 an hour. The next day, they'd appear at the Factory and Andy, whom we never introduced by name would take their Polaroids. And the next time we saw them at the Gilded Grape, they invariably would say, "Tell your friend I do a lot more for fifty bucks." (BC228)
Because of the interest at the exhibit by Italian journalists who asked Warhol if he was a Communist - Andy remarked later that night to Bob Colacello, "Maybe I should do real Communist paintings next. They would sell a lot in Italy." According to Colacello, "Thus was conceived the 1977 Hammers and Sickles series." (BC228)
One large painting from the Ladies and Gentlemen series went for $176,000 at Christies (from the estate of Jean-Michel Basquiat) - the highest price of anything sold in that sale.
According to Bob Colacello in Holy Terror, the Drag Queen paintings were never shown in the United States. (BC228) However, in the same book, Colacello mentioned that in March 1976, they accepted an ad for Interview magazine in the March 1976 issue from the Max Protech Gallery in Washington DC for a show of Drag Queen prints. (BC266)