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 appeared on the cover of
Texas-based metal band Drowning Pool's second album Desensitized and was featured in the music video for the album's first hit single "Step Up". Jane states that Drowning Pool is one of her favorite bands.
On the July 25, 2006 episode of The Tonight Show with Jay Leno during the "Jay Walking" segment, she gave her name as "Cindy", and said that she currently worked at Hooters. An adult magazine cover featuring her as Jesse Jane was then shown onscreen.
In 2005, she was featured as UnRated Magazine's Vixen, to launch the favorable music review magazine's new edition of Vixens. The films in which Digital Playground cast Jane, such as No Limits, Beat the Devil, and Loaded, proved popular enough to warrant her own line of sex toys, as well as secure nominations for several awards. She starred in the erotic film series "Pirates".
Jane co-hosts (with fellow Digital Playground contract performers Devon and Teagan Presley) the live, Internet-based, adult industry talk show DP Tonight. The show features industry gossip, adult film star guests and audience/host interactivity.
Jane was a guest star on the HBO dramedy series Entourage on the second season in the ninth episode. 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 March 2006, Jane and Kirsten Price became the hosts of Playboy TV's most popular live show, Night Calls. In addition, Jane also hosts Playboy TV's Naughty Amateur Home Videos and is the sex columnist for Cheri, with contributions starting in the January 2007 issue.
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 2009 Jesse appeared in the reality series The Bad Girls Club.
In a 2009 CNBC documentary titled "Porn: Business of Pleasure", Jesse was the focus of the final 10 minute segment detailing her career and her life outside the porn industry.
In 2000, Jane gave birth to a boy.
- 2003 Nightmoves Entertainment Awards - Best New Starlet (Editor's Choice)
- 2004 Venus Award - Best Actress USA
- 2004 Delta di Venere Award - Best American Actress
- 2006 AVN Award – Best All-Girl Sex Scene (Video) – Pirates
- 2006 Nightmoves Entertainment Awards - Best Actress (Editor's Choice)
- 2006 FOXE Award - Female Fan Favorite
- 2006 Scandinavian Adult Awards - Best Selling International Star
- 2007 AVN Award – Best All-Girl Sex Scene (Video) – Island Fever 4
- 2007 F.A.M.E. Award – Hottest Body
- 2007 Exotic Dancer Awards - Adult Movie Feature Entertainer of the Year
- 2007 Venus Award - Best US Actress
- 2008 F.A.M.E. Award – Hottest Body
- 2008 Medien eLINE Award - Best US Actress
- 2009 AVN Award – Best All-Girl Group Sex Scene – Cheerleaders
- 2009 F.A.M.E. Award – Hottest Body
- 2009 Hot d'Or – Best American Actress – Pirates II: Stagnetti’s Revenge