Leatherdale started his career in New York City during the early eighties where he first served as Robert Mapplethorpe's office manager. Also an assistant curator to Sam Wagstaff, he soon became involved in documenting the vibrant club and fashion scene of New York City in the 1980s. He was featured in The New Yorker, Elle, Vanity Fair, Artforum, and Art in America and has collaborated with such artists as Madonna, Trisha Brown, and Kathy Acker.