Perhaps one of the most iconic "bad girl" pairings, Jessica Lovejoy (the Reverend’s daughter) proved to be even more devious than Bart. This relationship flipped the dynamic; Bart became the "good" influence while Jessica manipulated him into taking the fall for her antics. The imagery of Bart and Jessica together remains a fan favorite because it explores the idea that Bart actually has a moral compass when compared to a true sociopath. 3. Mary Spuckler: The One That Got Away