Amanda (born Armand) Lepore, New York's favorite post-op transsexual, has been a ubiquitous figure on the downtown nightlife scene since her induction in the early 1990s as a fixture at Michael Alig's "Disco 2000" parties. Lepore says she started wearing women's clothes at age 14, while still in Cedar Hill, NJ, where she was born. As a teenager, she befriended a transsexual at a club who started giving her hormone pills in exchange for Lepore's elaborate, handmade outfits. By the time she reached her senior year of high school, she'd undergone sexual reassignment surgery, paid for by her high school boyfriend's parents. After moving to New York, Lepore became a fixture at downtown clubs, where was paid, as she puts it, "to dress up, look freaky and flashy and over the top, and to dance." She gained wider renown through her friendship with superstar avant-garde photographer David LaChapelle, who considers Lepore his muse and has featured her in numerous projects, including a "Time Tranny" watch released by Swatch in 1999. In 2003, Lepore released her first single, a trance song written with her notable drag queen friend Lady Bunny, and has since released two albums and a number of singles ("My Pussy," "My Hair Looks Fierce," and "Cotton Candy," to name a few). She's also appeared in music videos by other artists, such as Elton John, Grace Jones, and her friend and frequent collaborator Cazwell.

[Image via Getty]