Jessica is the youngest child of Grace and Sam Bennett. She has a close relationship with her mother, and an antagonistic relationship with her sister Kay.

Mary Elizabeth Winstead, 1999 - 2000

Jessica was a quiet, perfect daughter. She was very close to her mother, working part-time in her mother's craft shop, even though she was only fourteen when the show started. While she loved her sister Kay, the two had an adversarial relationship, mostly because she knew that Kay was always scheming. When push came to shove, though, she was there for Kay, refusing to tell their parents that Kay knew Faith was Grace's sister for weeks before the rest of them found out the truth, and that Kay's schemes to get Miguel are the real reason that Faith and Grace never met. In part because she sees their love for each other, and in part to foil her scheming sibling, Jessica has always been a strong supporter of Charity and Miguel.

Jade Harlow, 2000 - 2003

Jessica's first major act on her own was to switch the voting box at the prom, which Kay had rigged to make sure Miguel was crowned king and she was crowned queen. She was in the background for a long period of time, but has been involved more and more in Kay's plans to get to Miguel by her own secret crush on Miguel. Unfortunately for Jessica, Reese can only see one woman...her older sister Kay. As the youngest character on the show, Jessica is the only one still in high-school. Jessica's faith in her family was shaken by the recent appearance of David and John, but she is determined to support her mother, and help her new brother John acclimate to life with siblings. Although she suspects David is up to no good, she has no idea that John isn't her brother.

Right now Jessica is stuck in the middle of the war between her sister, Kay, their parents, Miguel, and Charity. Jessica was the one who found Kay in Miguel's bed, and for just one moment, saw Charity in the bed instead of Kay. She knows that Miguel believed that it was Charity he was with, and has seen enough of her sister's hatred and evil over the years to know that Kay forced herself on Miguel. But she doesn't have much of a foothold right now, as everyone recently learned that Jessica was secretly involved with Kay's boyfriend Reese for the past few months. When Kay used magic on some popcorn in the hopes of breaking up Charity and Miguel, the plan backfired, and instead, it broke up Jessica and Reese. It wasn't long before Jessica realized her sister was behind her break-up.

Danica Stewart, 2003 - present

After graduating from high-school, Jessica got a job as a 'mark' cosmetics girl to help pay her way. Although currently attending college, much of her time is spent worrying about her family. Since Grace chose David Hastings, Jessica turned her back on her mother, in part because she was vulnerable to her sister Kay's manipulations. Jessica seemed to be the 'good' Bennett sister, never getting into trouble, but when Sam and Ivy's relationship started getting more serious, Jessica ended up on a downward spiral, and began acting out by cutting herself and smoking. She became a club girl, and it wasn't long before she was drugged and raped by an older man named Randy at a club.

Jessica soon met the older Spike, the owner of the sleaziest late-night dive in Harmony. Spike took advantage of Jessica's confusion and pain, and it wasn't long before he had his young lover addicted to drugs, and convinced her that she had to prostitute herself for him on the streets. He used guilt to convince her to do it, because her family was responsible for his club burning down. Every time she tried to fight him to go him, Spike would manipulate her into coming back to him, and it wasn't long before Jessica started experiencing blackouts and waking up next to dead johns. Although Paloma and Simone helped her to cover her role in the murders, even Jessica herself doesn't know if she actually killed the men.

Jessica kept trying to get away from Spike, and it seemed like she finally did in Rome, but even though she was at the point where she was holding a gun on him, Spike again convinced her that he was the only one who was good for her, insisting that she would bring shame upon her family. When they finally caught up to her and Spike and told them that Jessica could put him away, she blurted out that she couldn't -- he was now her husband!