ROLLERENA FAIRY GODMOTHER came into being on the evening of Saturday, September 16, 1972 through and by a young man from Kentucky who put on a gown, a 1950s hat, and a straw basket and skated up and down Christopher Street in Greenwich Village, New York City. Over time, Rollerena added to her outfit: rhinestone glasses, costume jewelry, a small horn, and a magic wand to bless mortals became regular accessories to her character. She skated in gay neighborhoods, the Easter Parade, Gay Pride marches and in popular discos. The creator of Rollerena did not consider himself a drag queen; instead she became the character of a Fairy Godmother.

The boy who would come to be known as Rollerena was born in Kentucky in 1948. As a teenager, he frequently traveled to Louisville by bus or hitchhiking, earned him the name “the bluegrass belle of the three counties.” At the age of 18, he registered for the draft and graduated from high school in the following spring. He served in the artillery infantry in Vietnam and returned to the States in September 1969. Upon arriving in New York City, he worked on Wall Street and even spent New Year’s Eve of 1969 in Times Square.

He started roller skating to work in 1970 and was often seen practicing his skating on 79th Street and Fifth Avenue. By this time, he was given the nickname “Rollin’ Skeets” and was known to wear a visor, an umbrella on his head, a backpack and a little horn at his waist to alert foot traffic. At the 1971 Gay Pride Parade, he skated around as “Rollin’ Skeets”. He went by this name for two years, until Rollerena was born.

After stepping foot into an antique store on Christopher Street, Rollerena emerged in her classic costume and began skating around the Village. She then entered a bar and “the whole place went absolutely wild!” It was said that “a crowd gathered like they were awaiting Glinda landing in Oz.” She then officially debuted in the 1973 Easter Parade as “Roller Arena the Fairy Godmother” (later shortened to “Rollerena”). Although her skating was limited to well-heeled neighborhoods, gay spots and chic haunts like Studio 54, she became ever popular. As Rollerena became more well-known within and beyond her community, people began to request her presence at various events. She had a post office box, business representatives, disco events, postcards, and was featured in many newspaper articles, TV shows and radio talk programs.

Throughout her history, she collected thirty 1950s hats, costume jewelry earrings, and fifteen pairs of rhinestone glasses. Various newspapers gave different spellings to the Fairy Godmother and these spellings are used in this finding aid as they appear in the articles. They include: “Rollerina,” “Roller Rena,” “Rolla-Reena,” “Rollerarena,” and “Roll-Arena.”