- “You're bad, and I like it.”
- ―Jessica Lovejoy[src]
While appearing sweet and calm on the outside, Jessica actually has a penchant for mischief and chaos, and can cross the line farther than Bart himself, despite her being raised by very religious parents. Amongst boys smitten by her, she falls right into the role of femme fatale, and isn't afraid to use it. She has been portrayed as having the ability to draw young men under her spell; one, a library assistant, rode on a bicycle to pick her up as she hoodwinked Bart into cleaning the church steps in her stead. She uses her beauty to manipulate boys and uses timidity to manipulate adults and girls.
Jessica went to a boarding school, but was allegedly expelled for destroying school property including toilets, supposedly with a pipe bomb, and stealing from the school collection plate. After her expulsion, she briefly dated Bart Simpson. According to Bart's experiences with her, Jessica encouraged his negative behavior and eventually pushed him down an extremely steep hill littered with truck accidents on his skateboard. Later, Jessica went as far as to activate the fire alarm at Springfield Elementary during the school day as a prank, causing a mass panic at the school. It is stated (by Bart) that she has an IQ of 108, and that "she's like a Milk Dud; sweet on the outside, poison on the inside." She inevitably went too far, however, by stealing the collection money from the First Church of Springfield (where her father is minister) and blaming it on Bart. Lisa, however, brought her to justice. After showing the evidence that Jessica is bad, her father actively ignores the fact that his daughter is a criminal, and continues to blame the theft on Bart until Jessica finally admits to her crime. Later, Bart is once again taken in by her charms as he works to scrub clean the church steps (a punishment meant for Jessica) while she rides off on a date with another boy, one unidentified (yet allegedly well read) library volunteer, but comes to do a subpar job on the steps to punish her further.
Despite the fact that she's a wicked, misbehaving, antisocial girl, she does try to get attention from her father, who is shown to ignore and deny her behavioral problems. She also explains that her behavior, in part, is because of her desire for attention from her father.
Jessica has since made cameos throughout the series. She and her father were participants in Robot Rumble. Their creation, a centipede-like machine by the name of Kill-a-Puss, was defeated by "Chief Knock-A-Homer", Homer and Bart's entry. Jessica makes a cameo appearance as a player in a soccer game where she gets the ball past Sherri and Terri. However she is unfairly accused of committing a foul when Lisa unsuccessfully attempts to get the ball from her and trips. She was also taken to Weasel Island by her father on Mother's Day. When Springface was introduced to Springfield, she became one of Lewis' online friends. She then appeared in a photo that Bart kept alongside the photos of his other past girlfriends. It can be assumed that Bart actually didn't visit Jessica, unlike the rest of his ex-girlfriends, because of what happened between them during their relationship. She also appears in The Simpsons Movie sitting the front row at church when Reverend Lovejoy says, "Lord hear our prayer."
Jessica also appears in the new opening sequence, playing the flute in the school's music class.
Jessica has long straight black hair with bangs and a thick non-receding hairline. She usually wears pink and purple outfits. She also has high cheek bones, large dimples and eyelashes of unusually long length. Her usual outfit consists of a pink headband with a bow in her hair, a pink dress, a light purple T-shirt, and white socks with purple shoes.
Jessica is an expert troublemaker. As a reckless prankster, she gets along well with Bart to an extent. Putting on a front, she gets away with her crimes. Her disregard for social norms, rules, and obligations get other people in problematic situations. She doesn't listen to anyone, and is prone to putting people on edge. She is also an adrenaline junkie, attracted to risks and dangers. She has a passion for skateboards, motorcycles and snowboards. She mocks her father behind his back. She has such a fiery determination to ignore rules that even Bart Simpson thought she was going too far. She also occasionally smokes.
It’s possible that she might be adopted, since her mother is rumored to be transgender. However, this has not yet been explicitly confirmed.
Note: Most of her appearances are brief, background roles. The episode in which she has a star role is in bold.