James R. Herndon (July 2, 1892 – December 16, 1983) was Lexington's best-known and well-loved African-American
transvestite, appearing on the streets in drag as early as the 1920s.
Surprisingly, Herndon was not scorned but embraced by the community. Worked at
Good Samaritan Hospital for most of his life. He was generally known not by
his real name but by his Drag names, "Sweet Evening Breeze" or "Miss Sweets".
In a famous court case, Herndon, along with fellow drag queen Leigh Angelique, was responsible for overturning Lexington's archaic law on the books against crossdressing.
For his achievement of being himself against the odds, the Royal Sovereign Imperial Court of All Kentucky named its highest honor the James Herndon Award.
