It's not likely this was the "first" drag queen. He would've been imitating a "belle of the cakewalk" or a "cake-walk queen." This was entertainment for "the master" that later became a huge part of minstrel shows. "The Slow drag" was an extremely popular dance. Before becoming "ragtime," the musical genre was commonly referred to as one word: Drag.

"Cakewalkin' was a lot of fun durin' slavery time. Dey swep yards real clean and set benches for de party. Banjos wuz used for music makin'. De women's wor long, ruffled dresses wid hoops in 'em and de mens had on high hats, long split-tailed coats, and some of em used walkin' sticks. De couple dat danced best got a prize. Sometimes de slave owners come to dese parties 'cause dey enjoyed watchin' de dance, and dey 'cided who danced de best. Most parties durin' slavery time, wuz give on Saturday night durin' work sessions, but durin' winter dey wuz give on most any night." - Estella Jones.