Having been born in 1959, she started late in the adult film industry, and her reasons for doing so are not quite clear. During her adult video career spanning from 1989 to present, Chessie Moore performed in more than 200 adult videos; she also directed four videos during 1998. She is known for her intense performances during which she performs any sex acts called upon, including (at least in earlier instances) bestiality, and her ability to place herself in contortionist positions of an odd sort.

She states that her favorite male co-stars are Peter North and Ray Victory. Her first magazine spread was the cover feature of the April 1990 issue of Gent (an experience she reports disliking strongly). Although her first experience was negative, she subsequently appeared as a featured model in numerous magazines from 1990-1996, and fondly recalls her shoot for the July 1991 Hustler Erotic Video Guide, an issue that also featured a short article about her. Chessie has frequently demonstrated her front-bending contortionist skills by assuming a "pretzel" pose with one or both legs knotted behind her head while receiving cunnilingus or anal penetration.

Chessie and Steve still operate a personal phone sex service and a paysite. Although she has made numerous appearances in American strip clubs and pornographic magazines, today she prefers private functions for fans, including the production of made-to-order private videos. She advertises that she will perform on film whatever a fan requests, specifically making that video for them, with the rights to market it for others if she desires to do so.