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After being one of the top finalists in a local model search, Jane began working as a model for retail outlets such as 5-7-9 and David's Bridal. This work gained her a job doing a television commercial for Hooters restaurant. She also entered Hawaiian Tropic beauty contests, one of which led to her winning a walk-on role in the 2003 made for television movie, Baywatch: Hawaiian Wedding.
In August 2002, she was named "Miss Photogenic" by the American Dreams Pageant, and shot commercials for the pageant's sponsors. She embarked on a career as a top bikini model, although she did have a desire to perform in pornography. Jane read an article on Tera Patrick which said that Patrick worked for adult-film production company Digital Playground. She contacted them and was quickly signed to a contract. Her first scene was with Devon in the film No Limits. Within months of winning the contract, she appeared on Showtime Network's, Family Business, where she was filmed at the Adult Video News' awards show and convention.
Jane was a guest star on the HBO comedy series Entourage. The episode is entitled "I Love You Too", and features the foursome making a trip to Comicon where they get some help from the "Pussy Patrol" of which Jane is the leader.
In January 2007, an article in the New York Times stated that Jane intended to have her breast enhancement surgery re-done in an effort to enhance their appearance for high-definition movies. On her official website, she wrote that on 12 February she had her surgery.
In 2007, Jesse became a sex columnist for the Australian magazine Ralph, replying to letters from readers about sex and dating.